CHEBI:42504 - pentadecanoic acid

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ChEBI Name pentadecanoic acid
ChEBI ID CHEBI:42504
Definition A straight-chain saturated fatty acid containing fifteen-carbon atoms.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:39108, CHEBI:42502
Supplier Information ChemicalBook:CB7187490, eMolecules:530424, ZINC000030731069
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Pentadecylic acid, also known as pentadecanoic acid or C15:0, is an odd-chain saturated fatty acid. Its molecular formula is CH3(CH2)13CO2H. It is a colorless solid. A laboratory preparation involves permanganate oxidation of 1-hexadecene (CH3(CH2)13CH=CH2). It is one of the most common odd-chain fatty acids, although it is rare in nature. Pentadecylic acid is found primarily in dairy fat, as well as in ruminant meat and some fish and plants. The butterfat in cow milk is its major dietary source, comprising 1.2% of cow milk fat. Rare genetic disorders causing unusually high concentrations of C15:0 and C17:0, including Refsum disease, Zellweger Syndrome, and propionic acidemia, confirmed endogenous synthesis of these odd-chain FAs in humans, involving alpha-oxidation.
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Formula C15H30O2
Net Charge 0
Average Mass 242.39750
Monoisotopic Mass 242.22458
InChI InChI=1S/C15H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15(16)17/h2-14H2,1H3,(H,16,17)
InChIKey WQEPLUUGTLDZJY-UHFFFAOYSA-N
SMILES CCCCCCCCCCCCCCC(O)=O
Metabolite of Species Details
Hypericum roeperianum (NCBI:txid269018) See: PubMed
Chlamydomonas reinhardtii (NCBI:txid3055) See: PubMed
Daphnia magna (NCBI:txid35525) See: PubMed
Homo sapiens (NCBI:txid9606) Found in blood serum (BTO:0000133). See: MetaboLights Study
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
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.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
food component
A physiological role played by any substance that is distributed in foodstuffs. It includes materials derived from plants or animals, such as vitamins or minerals, as well as environmental contaminants.
human blood serum metabolite
Any metabolite (endogenous or exogenous) found in human blood serum samples.
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ChEBI Ontology
Outgoing pentadecanoic acid (CHEBI:42504) has role Daphnia magna metabolite (CHEBI:83056)
pentadecanoic acid (CHEBI:42504) has role algal metabolite (CHEBI:84735)
pentadecanoic acid (CHEBI:42504) has role food component (CHEBI:78295)
pentadecanoic acid (CHEBI:42504) has role human blood serum metabolite (CHEBI:85234)
pentadecanoic acid (CHEBI:42504) has role plant metabolite (CHEBI:76924)
pentadecanoic acid (CHEBI:42504) is a long-chain fatty acid (CHEBI:15904)
pentadecanoic acid (CHEBI:42504) is a straight-chain saturated fatty acid (CHEBI:39418)
pentadecanoic acid (CHEBI:42504) is conjugate acid of pentadecanoate (CHEBI:78795)
Incoming (14R)-14-hydroxypentadecanoic acid (CHEBI:78996) has functional parent pentadecanoic acid (CHEBI:42504)
(3S,4S)-3-hydroxytetradecane-1,3,4-tricarboxylic acid (CHEBI:15615) has functional parent pentadecanoic acid (CHEBI:42504)
1,2-di-O-pentadecanoyl-sn-glycero-3-phosphocholine (CHEBI:86088) has functional parent pentadecanoic acid (CHEBI:42504)
1-docosanoyl-2-pentadecanoyl-sn-glycero-3-phosphoethanolamine (CHEBI:134229) has functional parent pentadecanoic acid (CHEBI:42504)
1-nonanoyl-2-pentadecanoyl-sn-glycero-3-phosphocholine (CHEBI:86281) has functional parent pentadecanoic acid (CHEBI:42504)
1-octadecanoyl-2-pentadecanoyl-sn-glycero-3-phosphocholine (CHEBI:134076) has functional parent pentadecanoic acid (CHEBI:42504)
1-oleoyl-2-pentadecanoyl-sn-glycero-3-phosphate (CHEBI:74852) has functional parent pentadecanoic acid (CHEBI:42504)
1-pentadecanoyl-2-[(5Z,8Z,11Z,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:86344) has functional parent pentadecanoic acid (CHEBI:42504)
1-pentadecanoyl-2-docosanoyl-sn-glycero-3-phosphoethanolamine (CHEBI:134232) has functional parent pentadecanoic acid (CHEBI:42504)
1-pentadecanoyl-2-linoleoyl-sn-glycero-3-phosphocholine (CHEBI:133617) has functional parent pentadecanoic acid (CHEBI:42504)
1-pentadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine (CHEBI:134075) has functional parent pentadecanoic acid (CHEBI:42504)
1-pentadecanoyl-2-octadecanoyl-sn-glycero-3-phosphoethanolamine (CHEBI:136139) has functional parent pentadecanoic acid (CHEBI:42504)
1-pentadecanoyl-2-oleoyl-sn-glycero-3-phosphocholine (CHEBI:133623) has functional parent pentadecanoic acid (CHEBI:42504)
1-pentadecanoyl-sn-glycero-3-phosphocholine (CHEBI:131924) has functional parent pentadecanoic acid (CHEBI:42504)
14-methylpentadecanoic acid (CHEBI:84890) has functional parent pentadecanoic acid (CHEBI:42504)
15-hydroxypentadecanoic acid (CHEBI:79169) has functional parent pentadecanoic acid (CHEBI:42504)
2-hydroxypentadecanoic acid (CHEBI:84853) has functional parent pentadecanoic acid (CHEBI:42504)
N-(pentadecanoyl)sphinganine-1-phosphocholine (CHEBI:72759) has functional parent pentadecanoic acid (CHEBI:42504)
N-pentadecanoylsphingosine-1-phosphocholine (CHEBI:64485) has functional parent pentadecanoic acid (CHEBI:42504)
O-pentadecanoylcarnitine (CHEBI:131886) has functional parent pentadecanoic acid (CHEBI:42504)
cholesteryl pentadecanoate (CHEBI:84318) has functional parent pentadecanoic acid (CHEBI:42504)
DG(15:0/15:0/0:0) (CHEBI:88705) has functional parent pentadecanoic acid (CHEBI:42504)
methyl pentadecanoate (CHEBI:142657) has functional parent pentadecanoic acid (CHEBI:42504)
pentadecanoyl-CoA (CHEBI:74574) has functional parent pentadecanoic acid (CHEBI:42504)
pentadecanoate (CHEBI:78795) is conjugate base of pentadecanoic acid (CHEBI:42504)
IUPAC Name
pentadecanoic acid
Synonyms Sources
15:00 ChEBI
C15 ChEBI
C15:0 ChEBI
n-pentadecanoic acid NIST Chemistry WebBook
n-Pentadecanoic acid KEGG COMPOUND
PENTADECANOIC ACID PDBeChem
pentadecylic acid NIST Chemistry WebBook
Pentadecylic acid KEGG COMPOUND
Manual Xrefs Databases
C00007423 KNApSAcK
C16537 KEGG COMPOUND
F15 PDBeChem
HMDB0000826 HMDB
LMFA01010015 LIPID MAPS
Pentadecanoic_acid Wikipedia
View more database links
Registry Numbers Types Sources
1002-84-2 CAS Registry Number NIST Chemistry WebBook
1002-84-2 CAS Registry Number ChemIDplus
1773831 Reaxys Registry Number Reaxys
Citations
Tanemossu SA, Franke K, Arnold N, Schmidt J, Wabo HK, Tane P, Wessjohann LA (2014)
Rare biscoumarin derivatives and flavonoids from Hypericum riparium.
Phytochemistry 105, 171-177 [PubMed:24930002]
[show Abstract]
Coroian A, Erler S, Matea CT, Mireșan V, Răducu C, Bele C, Coroian CO (2013)
Seasonal changes of buffalo colostrum: physicochemical parameters, fatty acids and cholesterol variation.
Chemistry Central journal 7, 40 [PubMed:23442377]
[show Abstract]
Last Modified
06 July 2021