methyl-branched fatty acid |
|
CHEBI:62499 |
|
Any branched-chain fatty acid containing methyl branches only. |
|
This entity has been manually annotated by the ChEBI Team.
|
|
R. Stephan
|
|
|
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
|
|
View more via ChEBI Ontology
Outgoing
|
methyl-branched fatty acid
(CHEBI:62499)
is a
branched-chain fatty acid
(CHEBI:35819)
methyl-branched fatty acid
(CHEBI:62499)
is conjugate acid of
methyl-branched fatty acid anion
(CHEBI:67013)
|
|
Incoming
|
ω-hydroxy-15-methylpalmitic acid
(CHEBI:84939)
is a
methyl-branched fatty acid
(CHEBI:62499)
ω-hydroxyphytanic acid
(CHEBI:84925)
is a
methyl-branched fatty acid
(CHEBI:62499)
(+/-)-ethylitaconic acid
(CHEBI:200136)
is a
methyl-branched fatty acid
(CHEBI:62499)
(12)(13)-methyltetradecanoic acid
(CHEBI:232769)
is a
methyl-branched fatty acid
(CHEBI:62499)
(14)(15)-methylhexadecanoic acid
(CHEBI:232770)
is a
methyl-branched fatty acid
(CHEBI:62499)
(16)(17)-methyloctadecanoic acid
(CHEBI:232771)
is a
methyl-branched fatty acid
(CHEBI:62499)
(2E,6E,10E)-geranylgeranic acid
(CHEBI:84971)
is a
methyl-branched fatty acid
(CHEBI:62499)
(2E,6E,10E,14E)-ω-hydroxygeranylgeranic acid
(CHEBI:84977)
is a
methyl-branched fatty acid
(CHEBI:62499)
(2E,6E,11E,13E)-18-(2,6-dioxopiperidin-4-yl)-9-hydroxy-8-methoxy-10,12,14-trimethyl-15-oxooctadeca-2,6,11,13-tetraenoic acid
(CHEBI:183989)
is a
methyl-branched fatty acid
(CHEBI:62499)
(2S)-2-methylheptadecanoic acid
(CHEBI:85218)
is a
methyl-branched fatty acid
(CHEBI:62499)
(3E)-2-Propylpent-3-enoic acid
(CHEBI:195734)
is a
methyl-branched fatty acid
(CHEBI:62499)
(E)-11-methyldodec-2-enoic acid
(CHEBI:87153)
is a
methyl-branched fatty acid
(CHEBI:62499)
10,13-dimethyltetradecanoic acid
(CHEBI:149651)
is a
methyl-branched fatty acid
(CHEBI:62499)
10-methyldodecanoic acid
(CHEBI:84872)
is a
methyl-branched fatty acid
(CHEBI:62499)
10-methylundecanoic acid
(CHEBI:84889)
is a
methyl-branched fatty acid
(CHEBI:62499)
12-methyloctadecanoic acid
(CHEBI:85058)
is a
methyl-branched fatty acid
(CHEBI:62499)
12-methylpentadecanoic acid
(CHEBI:131411)
is a
methyl-branched fatty acid
(CHEBI:62499)
13-methylpentadecanoic acid
(CHEBI:131414)
is a
methyl-branched fatty acid
(CHEBI:62499)
14-methylhexadecanoic acid
(CHEBI:84874)
is a
methyl-branched fatty acid
(CHEBI:62499)
14-methylpentadecanoic acid
(CHEBI:84890)
is a
methyl-branched fatty acid
(CHEBI:62499)
16-methyl-octadeca-5Z,9Z,12Z-trienoic acid
(CHEBI:186921)
is a
methyl-branched fatty acid
(CHEBI:62499)
16-methylheptadecanoic acid
(CHEBI:84896)
is a
methyl-branched fatty acid
(CHEBI:62499)
16-methyloctadecanoic acid
(CHEBI:84875)
is a
methyl-branched fatty acid
(CHEBI:62499)
17-methyloctadecanoic acid
(CHEBI:133136)
is a
methyl-branched fatty acid
(CHEBI:62499)
18-methylicosanoic acid
(CHEBI:84877)
is a
methyl-branched fatty acid
(CHEBI:62499)
18-methylnonadecanoic acid
(CHEBI:84899)
is a
methyl-branched fatty acid
(CHEBI:62499)
2,2-dimethyl-4-pentenoic acid
(CHEBI:179475)
is a
methyl-branched fatty acid
(CHEBI:62499)
2,4-Dimethyl-2-pentenoic acid
(CHEBI:173500)
is a
methyl-branched fatty acid
(CHEBI:62499)
2,6-dimethylheptanoic acid
(CHEBI:143886)
is a
methyl-branched fatty acid
(CHEBI:62499)
2-ethyl-2-methyl valeric ccid
(CHEBI:179957)
is a
methyl-branched fatty acid
(CHEBI:62499)
2-ethyl-2-methyl-butanoic acid
(CHEBI:180006)
is a
methyl-branched fatty acid
(CHEBI:62499)
2-isopropyl trans-crotonic acid
(CHEBI:179477)
is a
methyl-branched fatty acid
(CHEBI:62499)
2-Methyl-2-pentenoic acid
(CHEBI:173385)
is a
methyl-branched fatty acid
(CHEBI:62499)
2-Methyl-3-pentenoic acid
(CHEBI:173389)
is a
methyl-branched fatty acid
(CHEBI:62499)
2-methylbut-2-enoic acid
(CHEBI:36432)
is a
methyl-branched fatty acid
(CHEBI:62499)
2-Methylglutaconic acid
(CHEBI:165425)
is a
methyl-branched fatty acid
(CHEBI:62499)
2-methylhexadecanoic acid
(CHEBI:85057)
is a
methyl-branched fatty acid
(CHEBI:62499)
2-methyloctadecanoic acid
(CHEBI:144310)
is a
methyl-branched fatty acid
(CHEBI:62499)
2-methylvaleric acid
(CHEBI:167644)
is a
methyl-branched fatty acid
(CHEBI:62499)
2-n-Propyl-2-pentenoic acid
(CHEBI:80639)
is a
methyl-branched fatty acid
(CHEBI:62499)
2-n-Propyl-3-pentenoic acid
(CHEBI:80640)
is a
methyl-branched fatty acid
(CHEBI:62499)
2-n-Propyl-4-pentenoic acid
(CHEBI:80634)
is a
methyl-branched fatty acid
(CHEBI:62499)
2-Propyl-2,4-pentadienoic acid
(CHEBI:80642)
is a
methyl-branched fatty acid
(CHEBI:62499)
2-propyl-2-pentenoic acid
(CHEBI:124938)
is a
methyl-branched fatty acid
(CHEBI:62499)
20-methyldocosanoic acid
(CHEBI:84878)
is a
methyl-branched fatty acid
(CHEBI:62499)
20-methylhenicosanoic acid
(CHEBI:84901)
is a
methyl-branched fatty acid
(CHEBI:62499)
22-methyltetracosanoic acid
(CHEBI:84882)
is a
methyl-branched fatty acid
(CHEBI:62499)
22-methyltricosanoic acid
(CHEBI:84903)
is a
methyl-branched fatty acid
(CHEBI:62499)
24-methylhexacosanoic acid
(CHEBI:84884)
is a
methyl-branched fatty acid
(CHEBI:62499)
24-methylpentacosanoic acid
(CHEBI:84905)
is a
methyl-branched fatty acid
(CHEBI:62499)
26-methylheptacosanoic acid
(CHEBI:84907)
is a
methyl-branched fatty acid
(CHEBI:62499)
26-methyloctacosanoic acid
(CHEBI:84885)
is a
methyl-branched fatty acid
(CHEBI:62499)
28-methylnonacosanoic acid
(CHEBI:84908)
is a
methyl-branched fatty acid
(CHEBI:62499)
28-methyltriacontanoic acid
(CHEBI:84887)
is a
methyl-branched fatty acid
(CHEBI:62499)
3,13,19-trimethyltricosanoic acid
(CHEBI:188172)
is a
methyl-branched fatty acid
(CHEBI:62499)
3,4-dimethyl valeric acid
(CHEBI:180004)
is a
methyl-branched fatty acid
(CHEBI:62499)
3,7-dimethylocta-2,6-dienoate(1−)
(CHEBI:142930)
is a
methyl-branched fatty acid
(CHEBI:62499)
3-[(methoxycarbonyl)amino]-2,2,3-trimethylbutanoic acid
(CHEBI:183336)
is a
methyl-branched fatty acid
(CHEBI:62499)
3-Isopropenylpentanedioic acid
(CHEBI:173787)
is a
methyl-branched fatty acid
(CHEBI:62499)
3-methyl-2Z-pentenoic acid
(CHEBI:180390)
is a
methyl-branched fatty acid
(CHEBI:62499)
3-Methyl-3Z-pentenoic acid
(CHEBI:165360)
is a
methyl-branched fatty acid
(CHEBI:62499)
3-methyl-4-pentenoic acid
(CHEBI:180391)
is a
methyl-branched fatty acid
(CHEBI:62499)
3-methylbut-2-enoic acid
(CHEBI:37127)
is a
methyl-branched fatty acid
(CHEBI:62499)
3-methylglutaconic acid
(CHEBI:144330)
is a
methyl-branched fatty acid
(CHEBI:62499)
3-methylundecanoic acid
(CHEBI:85059)
is a
methyl-branched fatty acid
(CHEBI:62499)
3-methylvaleric acid
(CHEBI:166883)
is a
methyl-branched fatty acid
(CHEBI:62499)
3-oxopristanic acid
(CHEBI:63891)
is a
methyl-branched fatty acid
(CHEBI:62499)
3-tert-Butyl-3-butenoic acid
(CHEBI:165365)
is a
methyl-branched fatty acid
(CHEBI:62499)
4,4-dimethyl valeric acid
(CHEBI:180005)
is a
methyl-branched fatty acid
(CHEBI:62499)
4,4-dimethyl-2E-pentenoic acid
(CHEBI:179474)
is a
methyl-branched fatty acid
(CHEBI:62499)
4,4-dimethyl-2Z-pentenoic acid
(CHEBI:179476)
is a
methyl-branched fatty acid
(CHEBI:62499)
4,8,12-trimethyltridecanoic acid
(CHEBI:58966)
is a
methyl-branched fatty acid
(CHEBI:62499)
4-((1-acetoxy-3-methylpentan-2-yl)amino)-3-methyl-4-oxobutanoic acid
(CHEBI:218501)
is a
methyl-branched fatty acid
(CHEBI:62499)
4-aminovaleric acid betaine
(CHEBI:145241)
is a
methyl-branched fatty acid
(CHEBI:62499)
4-Methyl-2-pentenoic acid
(CHEBI:173387)
is a
methyl-branched fatty acid
(CHEBI:62499)
4-methyl-4-pentenoic acid
(CHEBI:180384)
is a
methyl-branched fatty acid
(CHEBI:62499)
4-methylpent-3-enoic acid
(CHEBI:143856)
is a
methyl-branched fatty acid
(CHEBI:62499)
7-methyloctanoic acid
(CHEBI:37108)
is a
methyl-branched fatty acid
(CHEBI:62499)
alpha,alpha-dimethyl valeric acid
(CHEBI:180000)
is a
methyl-branched fatty acid
(CHEBI:62499)
alpha-ethyl valeric acid
(CHEBI:180002)
is a
methyl-branched fatty acid
(CHEBI:62499)
beta,beta-dimethyl valeric acid
(CHEBI:179999)
is a
methyl-branched fatty acid
(CHEBI:62499)
dimethylbutyric acid
(CHEBI:38648)
is a
methyl-branched fatty acid
(CHEBI:62499)
farnesoic acid
(CHEBI:36969)
is a
methyl-branched fatty acid
(CHEBI:62499)
geranic acid
(CHEBI:67264)
is a
methyl-branched fatty acid
(CHEBI:62499)
isobutyric acid
(CHEBI:16135)
is a
methyl-branched fatty acid
(CHEBI:62499)
isocaproic acid
(CHEBI:74903)
is a
methyl-branched fatty acid
(CHEBI:62499)
isoheptadecanoic acid
(CHEBI:70850)
is a
methyl-branched fatty acid
(CHEBI:62499)
isopentadecanoic acid
(CHEBI:39250)
is a
methyl-branched fatty acid
(CHEBI:62499)
Isopropenylacetic acid
(CHEBI:178220)
is a
methyl-branched fatty acid
(CHEBI:62499)
isotridecanoic acid
(CHEBI:77359)
is a
methyl-branched fatty acid
(CHEBI:62499)
methyl-branched fatty acid 11:0
(CHEBI:141073)
is a
methyl-branched fatty acid
(CHEBI:62499)
methyl-branched fatty acid 12:0
(CHEBI:141076)
is a
methyl-branched fatty acid
(CHEBI:62499)
methyl-branched fatty acid 14:0
(CHEBI:141079)
is a
methyl-branched fatty acid
(CHEBI:62499)
methyl-branched fatty acid 15:0
(CHEBI:141080)
is a
methyl-branched fatty acid
(CHEBI:62499)
methyl-branched fatty acid 16:0
(CHEBI:141081)
is a
methyl-branched fatty acid
(CHEBI:62499)
methyl-branched fatty acid 16:1(9Z)
(CHEBI:141082)
is a
methyl-branched fatty acid
(CHEBI:62499)
methyl-branched fatty acid 17:0
(CHEBI:141083)
is a
methyl-branched fatty acid
(CHEBI:62499)
methyl-branched fatty acid 18:0
(CHEBI:141084)
is a
methyl-branched fatty acid
(CHEBI:62499)
methyl-branched fatty acid 18:1
(CHEBI:141085)
is a
methyl-branched fatty acid
(CHEBI:62499)
methyl-branched fatty acid 18:2
(CHEBI:141086)
is a
methyl-branched fatty acid
(CHEBI:62499)
methyl-branched fatty acid 20:0
(CHEBI:141088)
is a
methyl-branched fatty acid
(CHEBI:62499)
methyl-branched fatty acid 20:1(11Z)
(CHEBI:141089)
is a
methyl-branched fatty acid
(CHEBI:62499)
methyl-branched fatty acid 21:0
(CHEBI:141091)
is a
methyl-branched fatty acid
(CHEBI:62499)
methyl-branched fatty acid 22:0
(CHEBI:141092)
is a
methyl-branched fatty acid
(CHEBI:62499)
methyl-branched fatty acid 22:1(13Z)
(CHEBI:141093)
is a
methyl-branched fatty acid
(CHEBI:62499)
methyl-branched fatty acid 23:0
(CHEBI:141095)
is a
methyl-branched fatty acid
(CHEBI:62499)
methylbutyric acid
(CHEBI:38653)
is a
methyl-branched fatty acid
(CHEBI:62499)
mycocerosic acid
(CHEBI:143082)
is a
methyl-branched fatty acid
(CHEBI:62499)
Pentanedioic acid 2-(1-methylethenyl)-5-methyl ester
(CHEBI:215248)
is a
methyl-branched fatty acid
(CHEBI:62499)
Pentanedioic acid 2-(1-methylethylidene)-5-methyl ester
(CHEBI:211326)
is a
methyl-branched fatty acid
(CHEBI:62499)
Pestalotiopin A
(CHEBI:202196)
is a
methyl-branched fatty acid
(CHEBI:62499)
phytanic acid
(CHEBI:16285)
is a
methyl-branched fatty acid
(CHEBI:62499)
pivalic acid
(CHEBI:45133)
is a
methyl-branched fatty acid
(CHEBI:62499)
pristanic acid
(CHEBI:51340)
is a
methyl-branched fatty acid
(CHEBI:62499)
trimethyl acrylic acid
(CHEBI:180389)
is a
methyl-branched fatty acid
(CHEBI:62499)
tuberculostearic acid
(CHEBI:68565)
is a
methyl-branched fatty acid
(CHEBI:62499)
Z-3-Methylpent-2-en-1,5-dioic acid
(CHEBI:198535)
is a
methyl-branched fatty acid
(CHEBI:62499)
methyl-branched fatty acid anion
(CHEBI:67013)
is conjugate base of
methyl-branched fatty acid
(CHEBI:62499)
|
methyl-branched fatty acids
|
ChEBI
|
Rontani JF, Zabeti N, Aubert C (2009) Double bond migration to methylidene positions during electron ionization mass spectrometry of branched monounsaturated fatty acid derivatives. Journal of the American Society for Mass Spectrometry 20, 1997-2005 [PubMed:19747846] [show Abstract] Electron ionization mass spectra of several monounsaturated methyl-branched fatty acid methyl and trimethylsilyl esters were examined. These spectra exhibited some intensive fragment ions, whose formation could be explained after double-bond migration to methylidene position. This preferential migration (substantiated by deuterium labeling) acts significantly in the case of monounsaturated fatty acid methyl and trimethylsilyl esters possessing a methyl branch localized between the penultimate and the C(4) positions (relative to the ester group), whatever the position of the double-bond. Allylic cleavage and gamma-hydrogen rearrangement of the ionized methylidene group thus formed afforded very interesting fragment ions, which could be particularly useful to determine branching positions of monounsaturated methyl-branched fatty acid methyl and trimethylsilyl esters without additional treatment. | Johnston JB, Kells PM, Podust LM, Ortiz de Montellano PR (2009) Biochemical and structural characterization of CYP124: a methyl-branched lipid omega-hydroxylase from Mycobacterium tuberculosis. Proceedings of the National Academy of Sciences of the United States of America 106, 20687-20692 (Source: SUBMITTER) [PubMed:19933331] [show Abstract] Mycobacterium tuberculosis (Mtb) produces a variety of methyl-branched lipids that serve important functions, including modulating the immune response during pathogenesis and contributing to a robust cell wall that is impermeable to many chemical agents. Here, we report characterization of Mtb CYP124 (Rv2266) that includes demonstration of preferential oxidation of methyl-branched lipids. Spectrophotometric titrations and analysis of reaction products indicate that CYP124 tightly binds and hydroxylates these substrates at the chemically disfavored omega-position. We also report X-ray crystal structures of the ligand-free and phytanic acid-bound protein at a resolution of 1.5 A and 2.1 A, respectively, which provide structural insights into a cytochrome P450 with predominant omega-hydroxylase activity. The structures of ligand-free and substrate-bound CYP124 reveal several differences induced by substrate binding, including reorganization of the I helix and closure of the active site by elements of the F, G, and D helices that bind the substrate and exclude solvent from the hydrophobic active site cavity. The observed regiospecific catalytic activity suggests roles of CYP124 in the physiological oxidation of relevant Mtb methyl-branched lipids. The enzymatic specificity and structures reported here provide a scaffold for the design and testing of specific inhibitors of CYP124. | Jackson M, Stadthagen G, Gicquel B (2007) Long-chain multiple methyl-branched fatty acid-containing lipids of Mycobacterium tuberculosis: biosynthesis, transport, regulation and biological activities. Tuberculosis (Edinburgh, Scotland) 87, 78-86 [PubMed:17030019] [show Abstract] The cell envelope of pathogenic mycobacteria is highly distinctive in that it contains a number of lipids esterified with structurally related long-chain multi-methyl-branched fatty acids. These lipids have long been thought to play important roles in the cell envelope structure as well as in the pathogenicity of the tubercle bacillus. This review summarizes what is known about the biosynthesis of long-chain multiple methyl-branched fatty acid-containing lipids in Mycobacterium tuberculosis and describes the most recent findings about their regulation, transport across the different layers of the cell envelope and their biological functions. |
|