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call loadScript javascripts\jsmol\core\package.js call loadScript javascripts\jsmol\core\core.z.js -- required by ClazzNode call loadScript javascripts\jsmol\J\awtjs2d\WebOutputChannel.js Jmol JavaScript applet jmolApplet0_object__6154525598135305__ initializing getValue debug = null getValue logLevel = null getValue allowjavascript = null AppletRegistry.checkIn(jmolApplet0_object__6154525598135305__) call loadScript javascripts\jsmol\core\corestate.z.js viewerOptions: { "name":"jmolApplet0_object","applet":true,"documentBase":"https://www.ebi.ac.uk/chebi/searchId.do;jsessionid=D346EF8034455895070C4C022C877027?chebiId=CHEBI%3A28842","platform":"J.awtjs2d.Platform","fullName":"jmolApplet0_object__6154525598135305__","display":"jmolApplet0_canvas2d","signedApplet":"true","appletReadyCallback":"Jmol._readyCallback","statusListener":"[J.appletjs.Jmol.MyStatusListener object]","codeBase":"https://www.ebi.ac.uk/chebi/javascripts/jsmol/","syncId":"6154525598135305","bgcolor":"#000" } (C) 2012 Jmol Development Jmol Version: 13.2.7 $Date: 2013-10-01 11:35:15 -0500 (Tue, 01 Oct 2013) $ java.vendor: j2s java.version: 0.0 os.name: j2s Access: ALL memory: 0.0/0.0 processors available: 1 useCommandThread: false appletId:jmolApplet0_object (signed) starting HoverWatcher_1 getValue emulate = null defaults = "Jmol" getValue boxbgcolor = null getValue bgcolor = #000 backgroundColor = "#000" getValue ANIMFRAMECallback = null getValue APPLETREADYCallback = Jmol._readyCallback APPLETREADYCallback = "Jmol._readyCallback" getValue ATOMMOVEDCallback = null getValue CLICKCallback = null getValue ECHOCallback = null getValue ERRORCallback = null getValue EVALCallback = null getValue HOVERCallback = null getValue LOADSTRUCTCallback = null getValue MEASURECallback = null getValue MESSAGECallback = null getValue MINIMIZATIONCallback = null getValue PICKCallback = null getValue RESIZECallback = null getValue SCRIPTCallback = null getValue SYNCCallback = null getValue STRUCTUREMODIFIEDCallback = null getValue doTranslate = null language=en_US getValue popupMenu = null getValue script = null Jmol applet jmolApplet0_object__6154525598135305__ ready call loadScript javascripts\jsmol\core\corescript.z.js call loadScript javascripts\jsmol\J\script\FileLoadThread.js starting QueueThread0_2 script 1 started starting HoverWatcher_3 starting HoverWatcher_4 The Resolver thinks Mol Marvin 12161112203D starting HoverWatcher_5 Time for openFile( Marvin 12161112203D 56 55 0 0 0 0 999 V2000 3.0821 4.5679 5.9627 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6582 5.2642 4.9460 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5964 5.1540 6.9038 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0352 3.0624 5.9092 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8519 2.5681 6.7425 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8531 1.0411 6.7621 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6782 0.5517 7.6117 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7188 -0.9758 7.7217 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5281 -1.6375 6.3504 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8831 -1.3912 5.8061 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9926 -2.0201 4.4143 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4234 -1.9091 3.8807 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8357 -0.4484 3.6431 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9131 0.2301 2.6206 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5996 1.4825 2.0494 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9348 2.4905 3.1549 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6811 3.2524 3.5984 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9866 4.0184 4.8938 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1744 4.9685 4.7007 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5990 5.5128 6.0684 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6817 6.2755 4.9749 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9827 2.6514 6.3188 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9153 2.7367 4.8538 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9032 2.9324 6.2936 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9423 2.9523 7.7810 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8069 0.6759 7.1993 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7491 0.6562 5.7251 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2759 0.8624 7.1346 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7473 0.9972 8.6271 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0930 -1.3110 8.4021 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7021 -1.2821 8.1385 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6911 -2.7320 6.4502 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2690 -1.2155 5.6381 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0713 -0.2984 5.7374 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6311 -1.8544 6.4845 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7086 -3.0924 4.4756 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3031 -1.4929 3.7209 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1171 -2.3634 4.6202 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4907 -2.4632 2.9200 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7793 0.1052 4.6047 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8788 -0.4237 3.2615 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6938 -0.4800 1.7948 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9646 0.5238 3.1189 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5400 1.1802 1.5407 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9198 1.9657 1.3155 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3574 1.9470 4.0269 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6840 3.2156 2.7712 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3826 3.9693 2.8040 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8541 2.5326 3.7781 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0928 4.6094 5.1869 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2304 3.2914 5.6978 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0218 4.4183 4.2388 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8754 5.8108 4.0406 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6095 5.1271 6.3225 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6245 6.6232 6.0331 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8715 5.1820 6.8403 H 0 0 0 0 0 0 0 0 0 0 0 0 19 20 1 0 0 0 0 18 19 1 0 0 0 0 17 18 1 0 0 0 0 16 17 1 0 0 0 0 15 16 1 0 0 0 0 14 15 1 0 0 0 0 13 14 1 0 0 0 0 12 13 1 0 0 0 0 11 12 1 0 0 0 0 10 11 1 0 0 0 0 9 10 1 0 0 0 0 8 9 1 0 0 0 0 7 8 1 0 0 0 0 6 7 1 0 0 0 0 5 6 1 0 0 0 0 4 5 1 0 0 0 0 1 4 1 0 0 0 0 1 3 2 0 0 0 0 1 2 1 0 0 0 0 21 2 1 0 0 0 0 22 4 1 0 0 0 0 23 4 1 0 0 0 0 24 5 1 0 0 0 0 25 5 1 0 0 0 0 26 6 1 0 0 0 0 27 6 1 0 0 0 0 28 7 1 0 0 0 0 29 7 1 0 0 0 0 30 8 1 0 0 0 0 31 8 1 0 0 0 0 32 9 1 0 0 0 0 33 9 1 0 0 0 0 34 10 1 0 0 0 0 35 10 1 0 0 0 0 36 11 1 0 0 0 0 37 11 1 0 0 0 0 38 12 1 0 0 0 0 39 12 1 0 0 0 0 40 13 1 0 0 0 0 41 13 1 0 0 0 0 42 14 1 0 0 0 0 43 14 1 0 0 0 0 44 15 1 0 0 0 0 45 15 1 0 0 0 0 46 16 1 0 0 0 0 47 16 1 0 0 0 0 48 17 1 0 0 0 0 49 17 1 0 0 0 0 50 18 1 0 0 0 0 51 18 1 0 0 0 0 52 19 1 0 0 0 0 53 19 1 0 0 0 0 54 20 1 0 0 0 0 55 20 1 0 0 0 0 56 20 1 0 0 0 0 M END): 16 ms reading 56 atoms ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false 1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them. Default Van der Waals type for model set to Babel 56 atoms created ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation Script completed Jmol script terminated
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Stearic acid ( STEER-ik, stee-ARR-ik) is a saturated fatty acid with an 18-carbon chain. The IUPAC name is octadecanoic acid. It is a soft waxy solid with the formula CH3(CH2)16CO2H. The triglyceride derived from three molecules of stearic acid is called stearin. Stearic acid is a prevalent fatty-acid in nature, found in many animal and vegetable fats, but is usually higher in animal fat than vegetable fat. It has a melting point of 69.4 °C (156.9 °F) °C and a pKa of 4.50.
Its name comes from the Greek word στέαρ "stéar", which means tallow. The salts and esters of stearic acid are called stearates. As its ester, stearic acid is one of the most common saturated fatty acids found in nature and in the food supply, following palmitic acid. Dietary sources of stearic acid include meat, poultry, fish, eggs, dairy products, and foods prepared with fats; beef tallow, lard, butterfat, cocoa butter, and shea butter are rich fat sources of stearic acid. |
Read full article at Wikipedia
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InChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20) |
QIQXTHQIDYTFRH-UHFFFAOYSA-N |
C(CCCCCCCCCC)CCCCCCC(=O)O |
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Neolitsea daibuensis
(IPNI:466954-1)
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Found in
root
(BTO:0001188).
Cold MeOH extract of dried root, obtained as a mixture of stearic acid and docosanoic acid
See:
PubMed
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Chlamydomonas reinhardtii
(NCBI:txid3055)
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See:
PubMed
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Daphnia magna
(NCBI:txid35525)
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See:
Mixtures of similarly acting compounds in Daphnia magna: From gene to metabolite and beyondTine Vandenbrouck, Oliver A.H. Jones, Nathalie Dom, Julian L. Griffin, Wim De CoenEnvironment International 36 (2010) 254-268
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Centella asiatica
(NCBI:txid48106)
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See:
MetaboLights Study
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Homo sapiens
(NCBI:txid9606)
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See:
PubMed
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Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
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View more via ChEBI Ontology
Outgoing
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octadecanoic acid
(CHEBI:28842)
has parent hydride
octadecane
(CHEBI:32926)
octadecanoic acid
(CHEBI:28842)
has role
Daphnia magna metabolite
(CHEBI:83056)
octadecanoic acid
(CHEBI:28842)
has role
algal metabolite
(CHEBI:84735)
octadecanoic acid
(CHEBI:28842)
has role
human metabolite
(CHEBI:77746)
octadecanoic acid
(CHEBI:28842)
has role
plant metabolite
(CHEBI:76924)
octadecanoic acid
(CHEBI:28842)
is a
long-chain fatty acid
(CHEBI:15904)
octadecanoic acid
(CHEBI:28842)
is a
saturated fatty acid
(CHEBI:26607)
octadecanoic acid
(CHEBI:28842)
is a
straight-chain saturated fatty acid
(CHEBI:39418)
octadecanoic acid
(CHEBI:28842)
is conjugate acid of
octadecanoate
(CHEBI:25629)
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Incoming
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α-D-Gal-(1→4)-β-D-Gal-(1→4)-β-D-Glc-(1↔1')-Cer(d18:1/18:0)
(CHEBI:84690)
has functional parent
octadecanoic acid
(CHEBI:28842)
α-Neu5Ac-(2→3)-β-D-Gal-(1→3)-β-D-GalNAc-(1→4)-[α-Neu5Ac-(2→8)-α-Neu5Ac-(2→8)-α-Neu5Ac-(2→3)]-β-D-Gal-(1→4)-β-D-Glc-(1↔1')-Cer(d18:1/18:0)
(CHEBI:84682)
has functional parent
octadecanoic acid
(CHEBI:28842)
α-Neu5Ac-(2→3)-β-D-Gal-(1→4)-β-D-Glc-(1↔1')-Cer(d18:1/18:0)
(CHEBI:84675)
has functional parent
octadecanoic acid
(CHEBI:28842)
β-D-galactosyl-(1→4)-β-D-glucosyl-(1↔1)-N-octadecanoylsphingosine
(CHEBI:84759)
has functional parent
octadecanoic acid
(CHEBI:28842)
β-D-galactosyl-(1↔1ʼ)-N-octadecanoylsphinganine
(CHEBI:90498)
has functional parent
octadecanoic acid
(CHEBI:28842)
β-D-galactosyl-N-octadecanoylsphingosine
(CHEBI:84720)
has functional parent
octadecanoic acid
(CHEBI:28842)
β-D-glucosyl-(1↔1ʼ)-N-octadecanoylsphinganine
(CHEBI:84697)
has functional parent
octadecanoic acid
(CHEBI:28842)
β-D-glucosyl-N-octadecanoylsphingosine
(CHEBI:84719)
has functional parent
octadecanoic acid
(CHEBI:28842)
β-GalNAc-(1→4)-[α-Neu5Ac-(2→8)-α-Neu5Ac-(2→8)-α-Neu5Ac-(2→3)]-β-Gal-(1→4)-β-Glc-(1→1')-Cer(d18:1/18:0)
(CHEBI:84685)
has functional parent
octadecanoic acid
(CHEBI:28842)
(13Z)-8-hydroxyoctadecene-9,11-diynoic acid
(CHEBI:73751)
has functional parent
octadecanoic acid
(CHEBI:28842)
(9R,10S)-dihydroxyoctadecanoic acid
(CHEBI:136767)
has functional parent
octadecanoic acid
(CHEBI:28842)
(9S,10R)-10-hydroxy-9-(phosphonooxy)octadecanoic acid
(CHEBI:85632)
has functional parent
octadecanoic acid
(CHEBI:28842)
(9S,10R)-dihydroxyoctadecanoic acid
(CHEBI:85633)
has functional parent
octadecanoic acid
(CHEBI:28842)
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoic acid
(CHEBI:49253)
has functional parent
octadecanoic acid
(CHEBI:28842)
1,2-dioctadecanoyl-sn-glycero-3-cytidine 5'-diphosphate
(CHEBI:104121)
has functional parent
octadecanoic acid
(CHEBI:28842)
1,2-dioctadecanoyl-sn-glycerol
(CHEBI:41847)
has functional parent
octadecanoic acid
(CHEBI:28842)
1,2-dioleoyl-3-stearoyl-sn-glycerol
(CHEBI:77686)
has functional parent
octadecanoic acid
(CHEBI:28842)
1,2-distearoyl-sn-glycero-3-phosphocholine
(CHEBI:83718)
has functional parent
octadecanoic acid
(CHEBI:28842)
1,2-distearoyl-sn-glycero-3-phosphoserine
(CHEBI:84519)
has functional parent
octadecanoic acid
(CHEBI:28842)
1,2-distearoylphosphatidylethanolamine
(CHEBI:47764)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-O-stearoyl-N-acetylsphingosine
(CHEBI:76074)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-[(7Z,10Z,13Z,16Z)-docosatetraenoyl]-2-octadecanoyl-sn-glycero-3-phosphocholine
(CHEBI:86200)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-[(8Z,11Z,14Z,17Z)-icosatetraenoyl]-2-octadecanoyl-sn-glycero-3-phospho-1D-myo-inositol
(CHEBI:89250)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-[(9Z,12Z)-octadecadienoyl]-2-octadecanoyl-sn-glycero-3-phosphocholine
(CHEBI:86112)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-[(9Z,12Z)-octadecadienoyl]-2-octadecanoyl-sn-glycerol
(CHEBI:86337)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-acyl-2-octadecanoyl-sn-glycero-3-phosphate
(CHEBI:64864)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-acyl-2-stearoyl-sn-glycero-3-phospho-(1D-myo-inositol)
(CHEBI:84317)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-eicosanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine
(CHEBI:86166)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-heptadecanoyl-2-stearoyl-sn-glycero-3-phosphate
(CHEBI:85385)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine
(CHEBI:73000)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-hexadecanoyl-2-octadecanoyl-sn-glycerol
(CHEBI:86975)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-hexadecyl-2-octadecanoyl-sn-glycero-3-phosphocholine
(CHEBI:86229)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-hexanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine
(CHEBI:86282)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-myristoyl-2-stearoyl-sn-glycero-3-phosphocholine
(CHEBI:86090)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine
(CHEBI:84829)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoethanolamine
(CHEBI:79109)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-sn-glycero-3- phosphocholine
(CHEBI:73865)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-(5E,8E,11E,14E-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine
(CHEBI:84837)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-(6Z,9Z,12Z,15Z,18Z-docosapentaenoyl)-sn-glycero-3- phosphocholine
(CHEBI:84151)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycero-3-phosphocholine
(CHEBI:84565)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-(9Z)-hexadecenoyl-sn-glycero-3-phosphate
(CHEBI:75073)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-[(10Z,12Z)-octadecadienoyl]-sn-glycero-3-phosphocholine
(CHEBI:84819)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-[(11Z)-eicosenoyl]-sn-glycero-3-phosphocholine
(CHEBI:86173)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-[(13Z)-docosenoyl]-sn-glycero-3-phosphocholine
(CHEBI:86196)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-[(15Z)-tetracosenoyl]-sn-glycero-3-phosphocholine
(CHEBI:86219)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-[(2E,4E)-octadecadienoyl]-sn-glycero-3-phosphocholine
(CHEBI:84820)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-[(4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl]-sn-glycero-3-phosphoethanolamine
(CHEBI:131665)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-[(5Z,8Z,11Z)-eicosatrienoyl]-sn-glycero-3-phosphocholine
(CHEBI:86176)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-[(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl]-sn-glycero-3-phosphocholine
(CHEBI:86181)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-[(6Z,9Z)-octadecadienoyl]-sn-glycero-3-phosphocholine
(CHEBI:84821)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-[(6Z,9Z,12Z)-octadecatrienoyl]-sn-glycero-3-phosphocholine
(CHEBI:86117)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-[(6Z,9Z,12Z,15Z)-octadecatetraenoyl]-sn-glycero-3-phosphocholine
(CHEBI:86134)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-[(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl]-sn-glycero-3-phosphocholine
(CHEBI:86203)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-[(8Z,10Z,12Z,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine
(CHEBI:84823)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-[(8Z,11Z,14Z)-eicosatrienoyl]-sn-glycero-3-phosphocholine
(CHEBI:86177)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine
(CHEBI:86097)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-[(9Z,11Z,13Z,15Z,17Z,19E)-docosahexaenoyl]-sn-glycero-3-phosphocholine
(CHEBI:84830)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-[(9Z,12Z)-octadecadienoyl]-sn-glycero-3-phosphocholine
(CHEBI:84822)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-acyl-sn-glycero-3-phospho-1D-myo-inositol
(CHEBI:65090)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-docosanoyl-sn-glycerol
(CHEBI:87241)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-dodecanoyl-sn-glycero-3-phosphocholine
(CHEBI:138215)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-eicosanoyl-sn-glycero-3-phosphocholine
(CHEBI:86167)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-hexanoyl-sn-glycero-3-phosphocholine
(CHEBI:138212)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-nonanoyl-sn-glycero-3-phosphocholine
(CHEBI:138214)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-octadecenoyl-sn-glycero-3-phosphocholine
(CHEBI:84818)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-octanoyl-sn-glycero-3-phosphocholine
(CHEBI:138213)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-pentadecanoyl-sn-glycero-3-phosphocholine
(CHEBI:134076)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-pentanoyl-sn-glycero-3-phosphocholine
(CHEBI:138211)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecanoyl-2-tetracosanoyl-sn-glycero-3-phosphocholine
(CHEBI:86212)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-octadecyl-2-octadecanoyl-sn-glycero-3-phosphocholine
(CHEBI:86239)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-oleoyl-2-stearoyl-sn-glycero-3-phospho-L-serine
(CHEBI:75103)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-oleoyl-2-stearoyl-sn-glycero-3-phosphocholine
(CHEBI:76073)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-oleoyl-2-stearoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:85076)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-oleoyl-2-stearoyl-sn-glycerol
(CHEBI:75448)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-palmitoleoyl-2-stearoyl-sn-glycero-3-phosphocholine
(CHEBI:84570)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-palmitoleoyl-2-stearoyl-sn-glycerol
(CHEBI:84418)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-palmitoyl-2-lauroyl-sn-glycero-3-phospho-(1ʼ-sn-glycerol)
(CHEBI:77122)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-palmitoyl-2-oleoyl-3-stearoyl-sn-glycerol
(CHEBI:77623)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-palmitoyl-2-stearoyl-sn-glycero-3-phosphoserine
(CHEBI:84520)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-palmitoyl-3-stearoyl-sn-glycerol
(CHEBI:77624)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-palmityl-2-acetyl-3-stearoyl-sn-glycerol
(CHEBI:77677)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-pentadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine
(CHEBI:134075)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-pentadecanoyl-2-octadecanoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:136139)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl 2-acylglycerolipid
(CHEBI:87007)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-(α-linolenoyl)-sn-glycero-3-phosphocholine
(CHEBI:78022)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-sn-glycero-3-phosphate
(CHEBI:77258)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-sn-glycerol
(CHEBI:77129)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycero-3-phosphoserine
(CHEBI:84506)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-(7Z,10Z,13Z,16Z-docosatetraenoyl)-sn-glycerol
(CHEBI:84435)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-(8-epi-prostaglandin F2α)-sn-glycero-3-phosphocholine
(CHEBI:77329)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-(8Z,11Z,14Z-icosa-8,11,14-trienoyl)-sn-glycerol
(CHEBI:84433)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-(8Z,11Z,14Z-icosatrienoyl)-sn-glycero-3-phosphoserine
(CHEBI:84512)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-acetyl-sn-glycero-3-phosphocholine
(CHEBI:75220)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-arachidonoyl-3-oleoyl-sn-glycerol
(CHEBI:75729)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphate
(CHEBI:77239)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-(1ʼ-sn-glycerol)
(CHEBI:75646)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-(1D-myo-inositol 3,4,5-triphosphate)
(CHEBI:83980)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-1D-myo-inositol
(CHEBI:84153)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-biphosphate
(CHEBI:77276)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-1D-myo-inositol 4-phosphate
(CHEBI:77271)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-arachidonoyl-sn-glycero-3-phospho-1D-myo-inositol 5-phosphate
(CHEBI:77345)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphocholine
(CHEBI:74965)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:79110)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-arachidonoyl-sn-glycero-3-phosphoserine
(CHEBI:79113)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-arachidonoyl-sn-glycerol
(CHEBI:75728)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-arachidonoylglycerol
(CHEBI:83288)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-arachidonoylphosphatidic acid
(CHEBI:84165)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-linoleoyl-sn-glycero-3-phosphate
(CHEBI:77248)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-linoleoyl-sn-glycero-3-phospho-1D-myo-inositol 5-phosphate
(CHEBI:77344)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-linoleoyl-sn-glycero-3-phospho-L-serine
(CHEBI:84513)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-linoleoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:133600)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-linoleoyl-sn-glycerol
(CHEBI:77097)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-myristoyl-sn-glycero-3-phosphocholine
(CHEBI:86089)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-oleoyl-sn-glycero-3-phosphate
(CHEBI:74847)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-oleoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-biphosphate
(CHEBI:77279)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-oleoyl-sn-glycero-3-phospho-1D-myo-inositol 4-phosphate
(CHEBI:77277)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-oleoyl-sn-glycero-3-phospho-1D-myo-inositol 5-phosphate
(CHEBI:77347)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-oleoyl-sn-glycero-3-phosphoserine
(CHEBI:79096)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-oleoylglycerol
(CHEBI:75590)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-2-palmitoyl-sn-glycero-3-phosphocholine
(CHEBI:75026)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-sn-glycero-3-phosphate
(CHEBI:74850)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-sn-glycero-3-phospho-1D-myo-inositol
(CHEBI:83054)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-sn-glycero-3-phosphocholine
(CHEBI:73858)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:83047)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-stearoyl-sn-glycero-3-phosphoserine
(CHEBI:85403)
has functional parent
octadecanoic acid
(CHEBI:28842)
1-tetracosanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine
(CHEBI:86208)
has functional parent
octadecanoic acid
(CHEBI:28842)
10-hydroxyoctadecanoic acid
(CHEBI:143095)
has functional parent
octadecanoic acid
(CHEBI:28842)
10-PAHSA
(CHEBI:84460)
has functional parent
octadecanoic acid
(CHEBI:28842)
11-PAHSA
(CHEBI:84464)
has functional parent
octadecanoic acid
(CHEBI:28842)
12-(octadecanoyloxy)octadecanoic acid
(CHEBI:137089)
has functional parent
octadecanoic acid
(CHEBI:28842)
12-(phosphonooxy)octadecanoic acid
(CHEBI:85133)
has functional parent
octadecanoic acid
(CHEBI:28842)
12-methyloctadecanoic acid
(CHEBI:85058)
has functional parent
octadecanoic acid
(CHEBI:28842)
12-PAHSA
(CHEBI:84468)
has functional parent
octadecanoic acid
(CHEBI:28842)
13-(octadecanoyloxy)octadecanoic acid
(CHEBI:137091)
has functional parent
octadecanoic acid
(CHEBI:28842)
13-PAHSA
(CHEBI:84469)
has functional parent
octadecanoic acid
(CHEBI:28842)
16-DOXYL-stearic acid
(CHEBI:184306)
has functional parent
octadecanoic acid
(CHEBI:28842)
16-methyloctadecanoic acid
(CHEBI:84875)
has functional parent
octadecanoic acid
(CHEBI:28842)
17-methyloctadecanoic acid
(CHEBI:133136)
has functional parent
octadecanoic acid
(CHEBI:28842)
2,3-distearoyl-sn-glycerol
(CHEBI:77395)
has functional parent
octadecanoic acid
(CHEBI:28842)
2-methyloctadecanoic acid
(CHEBI:144310)
has functional parent
octadecanoic acid
(CHEBI:28842)
2-octadecanoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:133145)
has functional parent
octadecanoic acid
(CHEBI:28842)
2-oxooctadecanoic acid
(CHEBI:30820)
has functional parent
octadecanoic acid
(CHEBI:28842)
2-stearoyl-sn-glycero-3-phosphocholine
(CHEBI:76076)
has functional parent
octadecanoic acid
(CHEBI:28842)
2-stearoylglycerol
(CHEBI:75456)
has functional parent
octadecanoic acid
(CHEBI:28842)
3-oxooctadecanoic acid
(CHEBI:50576)
has functional parent
octadecanoic acid
(CHEBI:28842)
5-DOXYL-stearic acid
(CHEBI:184308)
has functional parent
octadecanoic acid
(CHEBI:28842)
5-PAHSA
(CHEBI:84457)
has functional parent
octadecanoic acid
(CHEBI:28842)
7-PAHSA
(CHEBI:84479)
has functional parent
octadecanoic acid
(CHEBI:28842)
8-PAHSA
(CHEBI:84486)
has functional parent
octadecanoic acid
(CHEBI:28842)
9-(octadecanoyloxy)octadecanoic acid
(CHEBI:137097)
has functional parent
octadecanoic acid
(CHEBI:28842)
9-PAHSA
(CHEBI:84425)
has functional parent
octadecanoic acid
(CHEBI:28842)
all-trans-retinyl stearate
(CHEBI:70761)
has functional parent
octadecanoic acid
(CHEBI:28842)
N-(octadecanoyl)-pentadecasphing-4-enine-1-phosphoethanolamine
(CHEBI:86516)
has functional parent
octadecanoic acid
(CHEBI:28842)
N-(octadecanoyl)ethanolamine
(CHEBI:85299)
has functional parent
octadecanoic acid
(CHEBI:28842)
N-(octadecanoyl)hexadecasphingosine-1-phosphocholine
(CHEBI:136273)
has functional parent
octadecanoic acid
(CHEBI:28842)
N-octadecanoyl-(4E,14Z)-sphingadienine
(CHEBI:136461)
has functional parent
octadecanoic acid
(CHEBI:28842)
N-octadecanoyl-15-methylhexadecasphingosine-1-phosphocholine
(CHEBI:119713)
has functional parent
octadecanoic acid
(CHEBI:28842)
N-octadecanoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:85668)
has functional parent
octadecanoic acid
(CHEBI:28842)
N-octadecanoylglycine
(CHEBI:136623)
has functional parent
octadecanoic acid
(CHEBI:28842)
N-octadecanoylsphingadienine-1-phosphocholine
(CHEBI:136281)
has functional parent
octadecanoic acid
(CHEBI:28842)
N-octadecanoylsphingosine
(CHEBI:72961)
has functional parent
octadecanoic acid
(CHEBI:28842)
N-octadecanoylsphingosine 1-phosphate
(CHEBI:73144)
has functional parent
octadecanoic acid
(CHEBI:28842)
N-octodecanoylsphinganine
(CHEBI:67033)
has functional parent
octadecanoic acid
(CHEBI:28842)
N-stearoyl-1,2-dioleoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:85791)
has functional parent
octadecanoic acid
(CHEBI:28842)
N-stearoyl-1-oleoyl-sn-glycero-3-phosphoethanolamine
(CHEBI:85660)
has functional parent
octadecanoic acid
(CHEBI:28842)
N-stearoyl-D-galactosylsphingosine
(CHEBI:83867)
has functional parent
octadecanoic acid
(CHEBI:28842)
N-stearoylhexadecasphinganine
(CHEBI:82811)
has functional parent
octadecanoic acid
(CHEBI:28842)
N-stearoylserotonin
(CHEBI:134065)
has functional parent
octadecanoic acid
(CHEBI:28842)
N-stearoylsphingosine-1-phosphocholine
(CHEBI:83358)
has functional parent
octadecanoic acid
(CHEBI:28842)
N-stearoyltaurine
(CHEBI:132479)
has functional parent
octadecanoic acid
(CHEBI:28842)
O-octadecanoyl-L-carnitine
(CHEBI:84644)
has functional parent
octadecanoic acid
(CHEBI:28842)
O-stearoylcarnitine
(CHEBI:73074)
has functional parent
octadecanoic acid
(CHEBI:28842)
butyl octadecanoate
(CHEBI:85983)
has functional parent
octadecanoic acid
(CHEBI:28842)
CDP-1-stearoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-sn-glycerol
(CHEBI:85846)
has functional parent
octadecanoic acid
(CHEBI:28842)
CDP-1-stearoyl-2-arachidonoyl-sn-glycerol
(CHEBI:85829)
has functional parent
octadecanoic acid
(CHEBI:28842)
CDP-1-stearoyl-2-linoleoyl-sn-glycerol
(CHEBI:85838)
has functional parent
octadecanoic acid
(CHEBI:28842)
CDP-1-stearoyl-2-oleoyl-sn-glycerol
(CHEBI:85841)
has functional parent
octadecanoic acid
(CHEBI:28842)
cholesteryl stearate
(CHEBI:82750)
has functional parent
octadecanoic acid
(CHEBI:28842)
epoxystearic acid
(CHEBI:134617)
has functional parent
octadecanoic acid
(CHEBI:28842)
hydroxyoctadecanoic acid
(CHEBI:24747)
has functional parent
octadecanoic acid
(CHEBI:28842)
monoacylglycerol 18:0
(CHEBI:87255)
has functional parent
octadecanoic acid
(CHEBI:28842)
octadecanamide
(CHEBI:34900)
has functional parent
octadecanoic acid
(CHEBI:28842)
octadecanoate ester
(CHEBI:75925)
has functional parent
octadecanoic acid
(CHEBI:28842)
stearonitrile
(CHEBI:133638)
has functional parent
octadecanoic acid
(CHEBI:28842)
stearoyl-CoA
(CHEBI:15541)
has functional parent
octadecanoic acid
(CHEBI:28842)
tristearoylglycerol
(CHEBI:45956)
has functional parent
octadecanoic acid
(CHEBI:28842)
tuberculostearic acid
(CHEBI:68565)
has functional parent
octadecanoic acid
(CHEBI:28842)
corn oil
(CHEBI:195250)
has part
octadecanoic acid
(CHEBI:28842)
soybean oil
(CHEBI:166975)
has part
octadecanoic acid
(CHEBI:28842)
octadecanoate
(CHEBI:25629)
is conjugate base of
octadecanoic acid
(CHEBI:28842)
|
18:0
|
ChEBI
|
acide octadécanoïque
|
ChEBI
|
acide stéarique
|
ChEBI
|
C18:0
|
ChemIDplus
|
CH3‒[CH2]16‒COOH
|
IUPAC
|
n-octadecanoic acid
|
NIST Chemistry WebBook
|
Octadecanoic acid
|
KEGG COMPOUND
|
Octadecansäure
|
ChemIDplus
|
octadecoic acid
|
ChEBI
|
Oktadekansäure
|
ChEBI
|
STEARIC ACID
|
PDBeChem
|
stearic acid
|
ChEBI
|
Stearinsäure
|
ChemIDplus
|
4611
|
DrugCentral
|
C00001238
|
KNApSAcK
|
C01530
|
KEGG COMPOUND
|
D00119
|
KEGG DRUG
|
DB03193
|
DrugBank
|
HMDB0000827
|
HMDB
|
LMFA01010018
|
LIPID MAPS
|
STE
|
PDBeChem
|
Stearic_acid
|
Wikipedia
|
STEARIC_ACID
|
MetaCyc
|
View more database links |
11738
|
Gmelin Registry Number
|
Gmelin
|
57-11-4
|
CAS Registry Number
|
NIST Chemistry WebBook
|
57-11-4
|
CAS Registry Number
|
ChemIDplus
|
608585
|
Reaxys Registry Number
|
Reaxys
|
Mansour S, Tocheva AS, Cave-Ayland C, Machelett MM, Sander B, Lissin NM, Molloy PE, Baird MS, Stübs G, Schröder NW, Schumann RR, Rademann J, Postle AD, Jakobsen BK, Marshall BG, Gosain R, Elkington PT, Elliott T, Skylaris CK, Essex JW, Tews I, Gadola SD (2016) Cholesteryl esters stabilize human CD1c conformations for recognition by self-reactive T cells. Proceedings of the National Academy of Sciences of the United States of America 113, E1266-75 [PubMed:26884207] [show Abstract] Cluster of differentiation 1c (CD1c)-dependent self-reactive T cells are abundant in human blood, but self-antigens presented by CD1c to the T-cell receptors of these cells are poorly understood. Here we present a crystal structure of CD1c determined at 2.4 Å revealing an extended ligand binding potential of the antigen groove and a substantially different conformation compared with known CD1c structures. Computational simulations exploring different occupancy states of the groove reenacted these different CD1c conformations and suggested cholesteryl esters (CE) and acylated steryl glycosides (ASG) as new ligand classes for CD1c. Confirming this, we show that binding of CE and ASG to CD1c enables the binding of human CD1c self-reactive T-cell receptors. Hence, human CD1c adopts different conformations dependent on ligand occupancy of its groove, with CE and ASG stabilizing CD1c conformations that provide a footprint for binding of CD1c self-reactive T-cell receptors. | Bordbar A, Mo ML, Nakayasu ES, Schrimpe-Rutledge AC, Kim YM, Metz TO, Jones MB, Frank BC, Smith RD, Peterson SN, Hyduke DR, Adkins JN, Palsson BO (2012) Model-driven multi-omic data analysis elucidates metabolic immunomodulators of macrophage activation. Molecular systems biology 8, 558 [PubMed:22735334] [show Abstract] Macrophages are central players in immune response, manifesting divergent phenotypes to control inflammation and innate immunity through release of cytokines and other signaling factors. Recently, the focus on metabolism has been reemphasized as critical signaling and regulatory pathways of human pathophysiology, ranging from cancer to aging, often converge on metabolic responses. Here, we used genome-scale modeling and multi-omics (transcriptomics, proteomics, and metabolomics) analysis to assess metabolic features that are critical for macrophage activation. We constructed a genome-scale metabolic network for the RAW 264.7 cell line to determine metabolic modulators of activation. Metabolites well-known to be associated with immunoactivation (glucose and arginine) and immunosuppression (tryptophan and vitamin D3) were among the most critical effectors. Intracellular metabolic mechanisms were assessed, identifying a suppressive role for de-novo nucleotide synthesis. Finally, underlying metabolic mechanisms of macrophage activation are identified by analyzing multi-omic data obtained from LPS-stimulated RAW cells in the context of our flux-based predictions. Our study demonstrates metabolism's role in regulating activation may be greater than previously anticipated and elucidates underlying connections between activation and metabolic effectors. | Robinson DM, Martin NC, Robinson LE, Ahmadi L, Marangoni AG, Wright AJ (2009) Influence of interesterification of a stearic acid-rich spreadable fat on acute metabolic risk factors. Lipids 44, 17-26 [PubMed:18982377] [show Abstract] Chemical and enzymatic interesterification are used to create spreadable fats. However, a comparison between the two processes in terms of their acute metabolic effects has not yet been investigated. A randomised crossover study in obese (plasma TAG > 1.69 mmol/L, and BMI > 30 (BMI = kg/m(2)) or waist circumference > 102 cm, n = 11, age = 59.3 +/- 1.8 years) and non-obese (plasma triacylglycerol (TAG) < 1.69 mmol/L, and BMI < 30 or waist circumference < 102 cm, n = 10, age = 55.8 +/- 2.2 years) men was undertaken to compare the effects of chemical versus enzymatic interesterification on postprandial risk factors for type 2 diabetes (T2D) and cardiovascular disease (CVD). TAG, cholesterol, glucose, insulin and free fatty acid concentrations were measured for 6 h following consumption of 1 g fat/kg body mass of non-interesterified (NIE), chemically interesterified (CIE), enzymatically interesterified (EIE) stearic acid-rich fat spread or no fat, each with 50 g available carbohydrate from white bread. Interesterification did not affect postprandial glucose, insulin, free fatty acids or cholesterol (P > 0.05). Following ingestion of NIE, increases in serum oleic acid were observed, whereas both oleic and stearic acids were increased with CIE and EIE (P < 0.05). While postprandial TAG concentrations in non-obese subjects were not affected by fat treatment (P > 0.05), obese subjects had an 85% increase in TAGs with CIE versus NIE (P < 0.05). The differences in TAG response between non-obese and obese subjects suggest that interesterification may affect healthy individuals differently compared to those already at risk for T2D and/or CVD. | Evans LM, Cowey SL, Siegal GP, Hardy RW (2009) Stearate preferentially induces apoptosis in human breast cancer cells. Nutrition and cancer 61, 746-753 [PubMed:19838949] [show Abstract] Stearic acid (stearate) is an 18-carbon saturated fatty acid that has been shown to inhibit invasion and proliferation and induce apoptosis in various human cell types. The specificity of stearate-induced apoptosis for cancerous versus noncancerous breast cells has not been examined, and the mechanism underlying stearate-induced apoptosis is unknown. Morphological analysis, cell viability, and caspase-3 activity assays demonstrated that stearate activated apoptosis preferentially in cancerous breast cells in a time- and dose-dependent manner. Inhibition of de novo diacylgycerol synthesis or protein kinase C (PKC) blocked stearate-induced caspase-3 activity, indicating the involvement of a novel or classical PKC isozyme. To our knowledge this is the first study showing that stearate induces apoptosis preferentially in breast cancer cells and implicates protein kinase C in the signaling cascade. These results raise the possibility of dietary stearate having a beneficial role in the prevention or treatment of breast cancer. | Van Rhijn I, Young DC, De Jong A, Vazquez J, Cheng TY, Talekar R, Barral DC, León L, Brenner MB, Katz JT, Riese R, Ruprecht RM, O'Connor PB, Costello CE, Porcelli SA, Briken V, Moody DB (2009) CD1c bypasses lysosomes to present a lipopeptide antigen with 12 amino acids. The Journal of experimental medicine 206, 1409-1422 [PubMed:19468063] [show Abstract] The recent discovery of dideoxymycobactin (DDM) as a ligand for CD1a demonstrates how a nonribosomal lipopeptide antigen is presented to T cells. DDM contains an unusual acylation motif and a peptide sequence present only in mycobacteria, but its discovery raises the possibility that ribosomally produced viral or mammalian proteins that commonly undergo lipidation might also function as antigens. To test this, we measured T cell responses to synthetic acylpeptides that mimic lipoproteins produced by cells and viruses. CD1c presented an N-acyl glycine dodecamer peptide (lipo-12) to human T cells, and the response was specific for the acyl linkage as well as the peptide length and sequence. Thus, CD1c represents the second member of the CD1 family to present lipopeptides. lipo-12 was efficiently recognized when presented by intact cells, and unlike DDM, it was inactivated by proteases and augmented by protease inhibitors. Although lysosomes often promote antigen presentation by CD1, rerouting CD1c to lysosomes by mutating CD1 tail sequences caused reduction in lipo-12 presentation. Thus, although certain antigens require antigen processing in lysosomes, others are destroyed there, providing a hypothesis for the evolutionary conservation of large CD1 families containing isoforms that survey early endosomal pathways. | Castrillo JI, Zeef LA, Hoyle DC, Zhang N, Hayes A, Gardner DC, Cornell MJ, Petty J, Hakes L, Wardleworth L, Rash B, Brown M, Dunn WB, Broadhurst D, O'Donoghue K, Hester SS, Dunkley TP, Hart SR, Swainston N, Li P, Gaskell SJ, Paton NW, Lilley KS, Kell DB, Oliver SG (2007) Growth control of the eukaryote cell: a systems biology study in yeast. Journal of biology 6, 4 [PubMed:17439666] [show Abstract]
BackgroundCell growth underlies many key cellular and developmental processes, yet a limited number of studies have been carried out on cell-growth regulation. Comprehensive studies at the transcriptional, proteomic and metabolic levels under defined controlled conditions are currently lacking.ResultsMetabolic control analysis is being exploited in a systems biology study of the eukaryotic cell. Using chemostat culture, we have measured the impact of changes in flux (growth rate) on the transcriptome, proteome, endometabolome and exometabolome of the yeast Saccharomyces cerevisiae. Each functional genomic level shows clear growth-rate-associated trends and discriminates between carbon-sufficient and carbon-limited conditions. Genes consistently and significantly upregulated with increasing growth rate are frequently essential and encode evolutionarily conserved proteins of known function that participate in many protein-protein interactions. In contrast, more unknown, and fewer essential, genes are downregulated with increasing growth rate; their protein products rarely interact with one another. A large proportion of yeast genes under positive growth-rate control share orthologs with other eukaryotes, including humans. Significantly, transcription of genes encoding components of the TOR complex (a major controller of eukaryotic cell growth) is not subject to growth-rate regulation. Moreover, integrative studies reveal the extent and importance of post-transcriptional control, patterns of control of metabolic fluxes at the level of enzyme synthesis, and the relevance of specific enzymatic reactions in the control of metabolic fluxes during cell growth.ConclusionThis work constitutes a first comprehensive systems biology study on growth-rate control in the eukaryotic cell. The results have direct implications for advanced studies on cell growth, in vivo regulation of metabolic fluxes for comprehensive metabolic engineering, and for the design of genome-scale systems biology models of the eukaryotic cell. | Wang ZJ, Li GM, Nie BM, Lu Y, Yin M (2006) Neuroprotective effect of the stearic acid against oxidative stress via phosphatidylinositol 3-kinase pathway. Chemico-biological interactions 160, 80-87 [PubMed:16448636] [show Abstract] Stearic acid is a long-chain saturated fatty acid consisting of 18 carbon atoms without double bonds. In the present study, we reported the neuroprotective effects and mechanism of stearic acid on cortical or hippocampal slices insulted by oxygen-glucose deprivation, NMDA or hydrogen peroxide (H(2)O(2)) in vitro. Different types of models of brain slice injury in vitro were developed by 10 min of oxygen/glucose deprivation, 0.5 mM NMDA or 2 mM H(2)O(2), respectively. After 30 min of preincubation with stearic acid (3-30 microM), cortical or hippocampal slices were subjected to oxygen-glucose deprivation, NMDA or H(2)O(2). Then the tissue activities were evaluated by using the 2,3,5-triphenyltetrazolium chloride (TTC) method. Population spikes were recorded in randomly selected hippocampal slices. Stearic acid (3-30 microM) dose-dependently protected brain slices from oxygen-glucose deprivation, NMDA and H(2)O(2) insults. Its neuroprotective effect against H(2)O(2) insults can be completely blocked by wortmannin (inhibitor of PI3K) and partially blocked by H7 (inhibitor of PKC) or genistein (inhibitor of TPK). Treatment of cortical or hippocampal slices with 30 microM stearic acid resulted in a significant increase in PI3K activity at 5, 10, 30 and 60 min. These observations reveal that stearic acid can protect cortical or hippocampal slices against injury induced by oxygen-glucose deprivation, NMDA or H(2)O(2), and its neuroprotective effects are via phosphatidylinositol 3-kinase dependent mechanism. | Kim JY, Kinoshita M, Ohnishi M, Fukui Y (2001) Lipid and fatty acid analysis of fresh and frozen-thawed immature and in vitro matured bovine oocytes. Reproduction (Cambridge, England) 122, 131-138 [PubMed:11425337] [show Abstract] The lipid content and fatty acid composition of fresh immature and in vitro matured bovine oocytes cultured in media with or without serum, and also those of frozen-thawed immature oocytes were analysed. All oocytes were ranked (A or B) on the basis of their cytoplasmic quality. Fatty acid composition (mol %; w/w) in the total lipid fraction was analysed by gas chromatography. Triglyceride, total cholesterol, phospholipid (phosphocholine-containing phospholipid) and non-esterified fatty acid contents of immature and in vitro matured oocytes were determined using lipid analysis kits. Phosphocholine-containing phospholipid and non-esterified fatty acid contents were determined in frozen-thawed immature bovine oocytes. Palmitic acid was the most abundant fatty acid in immature oocytes (A: 35%, B: 36%), and in in vitro matured oocytes cultured in the medium containing serum (A: 36%, B: 35%) or polyvinyl alcohol (A: 33%, B: 36%). Oleic acid was the second most abundant fatty acid in all A ranked oocytes, whereas stearic acid was the second most abundant fatty acid in all B ranked oocytes. There were significant differences (P < 0.05) in linoleic and arachidonic acid fractions between A and B ranked immature oocytes. In vitro matured oocytes had significantly (P < 0.05) lower proportions of linoleic and arachidonic acids, and significantly (P < 0.01) lower contents of triglyceride and total cholesterol compared with those of immature oocytes. The fatty acid composition of in vitro matured oocytes cultured in medium containing fetal calf serum or polyvinyl alcohol was similar, but significant differences (P < 0.01) in triglyceride and the total cholesterol content were observed. There was a significant decrease (P < 0.05) in the arachidonic acid proportion in frozen-thawed immature oocytes compared with that in fresh immature oocytes. In addition, significant (P < 0.05) decreases in both phospholipid (15.8--10.6 pmol) and non-esterified fatty acid (11.0--4.1 pmol) were found in frozen--thawed immature oocytes. The results indicate that lipids are available for use as an energy source for maturation and that serum lipids are incorporated into the oocyte cytoplasm during in vitro maturation. The changes in the lipid content (mainly phospholipid) and fatty acid composition were also observed in frozen--thawed immature oocytes. The study indicates that the alteration of fatty acid composition in bovine oocytes might improve maturation and cryopreservation. | Okabe M, Tsuchiyama Y, Okamoto R (1993) Development of a cyclodextrin production process using specific adsorbents. Bioprocess technology 16, 109-130 [PubMed:7763343] [show Abstract] Novel adsorbents that are composed of ligand, spacer, and support were chemically synthesized, and the two consecutive screenings made it possible to determine the adsorbents that were most suitable for alpha- and beta-CD production, respectively. Stearic acid was the most effective ligand for alpha-CD, whereas cyclohexanepropanamide-n-caproic acid was best for beta-CD. The adsorption selectivity of adsorbents derived from carboxylic acids (stearic or palmitic acid) and Chitosan beads was almost 100%, and their adsorption capacities were large enough to meet the demand for economical production and purification of CDs on an industrial scale. Next we discussed a novel process of alpha-CD production using the newly synthesized adsorbent characterized by the exceedingly powerful selectivity of alpha-CD from other CDs. alpha-CD production was carried out in the closed system converted to CDs by CGTase, and the column was packed with the adsorbent selective for alpha-CD. The yield of alpha-CD was 22.3%, and alpha-CD occupied a fraction of 57.4% in the overall CD reaction mixture. In the batch system without adsorbent, the yields of alpha-CD and its fraction were 10.8 and 24%, respectively. This novel process is particularly useful for the large-scale production of alpha-CD, in which the use of organic solvent is not preferable. We will now develop a novel process for the industrial production of CDs other than alpha-CD, such as gamma-CD, by using specific adsorbents. |
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