CHEBI:28716 - palmitoleic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name palmitoleic acid
ChEBI ID CHEBI:28716
Definition A hexadec-9-enoic acid in which the double bond at position C-9 has cis configuration.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:7897, CHEBI:44696, CHEBI:25836
Supplier Information
Download Molfile XML SDF
Formula C16H30O2
Net Charge 0
Average Mass 254.409
Monoisotopic Mass 254.22458
InChI InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7-
InChIKey SECPZKHBENQXJG-FPLPWBNLSA-N
SMILES C(CCCCCCC/C=C\CCCCCC)(=O)O
Metabolite of Species Details
Daphnia galeata (NCBI:txid27404) See: Is the fatty acid composition of Daphnia galeata determined by the fatty acid composition of the ingested diet?Weers P.M.M., Siewertsen K., and Gulati R.D.Freshwater Biology (1997), 38, 731-738
Chlamydomonas reinhardtii (NCBI:txid3055) See: PubMed
Escherichia coli (NCBI:txid562) 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): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
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.
EC 3.1.1.1 (carboxylesterase) inhibitor
Any EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that inhibits the action of carboxylesterase (EC 3.1.1.1 ).
human blood serum metabolite
Any metabolite (endogenous or exogenous) found in human blood serum samples.
Daphnia galeata metabolite
A Daphnia metabolite produced by the species Daphnia galeata.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing palmitoleic acid (CHEBI:28716) has role Daphnia galeata metabolite (CHEBI:83038)
palmitoleic acid (CHEBI:28716) has role Escherichia coli metabolite (CHEBI:76971)
palmitoleic acid (CHEBI:28716) has role algal metabolite (CHEBI:84735)
palmitoleic acid (CHEBI:28716) has role EC 3.1.1.1 (carboxylesterase) inhibitor (CHEBI:78444)
palmitoleic acid (CHEBI:28716) has role human blood serum metabolite (CHEBI:85234)
palmitoleic acid (CHEBI:28716) is a hexadec-9-enoic acid (CHEBI:72004)
palmitoleic acid (CHEBI:28716) is conjugate acid of palmitoleate (CHEBI:32372)
Incoming 1,2,3-tripalmitoleoylglycerol (CHEBI:75841) has functional parent palmitoleic acid (CHEBI:28716)
1,2-di-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphate (CHEBI:75071) has functional parent palmitoleic acid (CHEBI:28716)
1,2-di-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphoethanolamine (CHEBI:138792) has functional parent palmitoleic acid (CHEBI:28716)
1,2-di-[(9Z)-hexadecenoyl]glycerol (CHEBI:131830) has functional parent palmitoleic acid (CHEBI:28716)
1,2-di-palmitoleoyl-2-sn-glycerol (CHEBI:84417) has functional parent palmitoleic acid (CHEBI:28716)
1,2-dipalmitoleoyl-sn-glycero-3-phosphocholine (CHEBI:83717) has functional parent palmitoleic acid (CHEBI:28716)
1,2-dipalmitoyl-3-palmitoleoyl-sn-glycerol (CHEBI:85427) has functional parent palmitoleic acid (CHEBI:28716)
1,3-dipalmitoleoylglycerol (CHEBI:75849) has functional parent palmitoleic acid (CHEBI:28716)
1-(1Z-hexadecenyl)-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholine (CHEBI:84562) has functional parent palmitoleic acid (CHEBI:28716)
1-(9Z)-octadecenoyl-2-(9Z)-hexadecenoyl-sn-glycero-3-phosphate (CHEBI:75074) has functional parent palmitoleic acid (CHEBI:28716)
1-[(9Z)-hexadecenoyl]-2-[(11Z)-octadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:84810) has functional parent palmitoleic acid (CHEBI:28716)
1-[(9Z)-hexadecenoyl]-2-[(5Z,8Z,11Z,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine (CHEBI:84816) has functional parent palmitoleic acid (CHEBI:28716)
1-[(9Z)-hexadecenoyl]-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:84811) has functional parent palmitoleic acid (CHEBI:28716)
1-[(9Z)-hexadecenoyl]-2-[(9Z)-tetradecenoyl]-sn-glycero-3-phosphocholine (CHEBI:86415) has functional parent palmitoleic acid (CHEBI:28716)
1-[(9Z)-hexadecenoyl]-2-acetyl-sn-glycero-3-phosphocholine (CHEBI:131659) has functional parent palmitoleic acid (CHEBI:28716)
1-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:73851) has functional parent palmitoleic acid (CHEBI:28716)
1-[(9Z)-hexadecenoyl]glycerol (CHEBI:133596) has functional parent palmitoleic acid (CHEBI:28716)
1-[(9Z)-hexadecenyl]-2-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:86425) has functional parent palmitoleic acid (CHEBI:28716)
1-[(9Z)-octadecenoyl]-2-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:86100) has functional parent palmitoleic acid (CHEBI:28716)
1-acyl-2-palmitoleoyl-sn-glycero-3-phosphocholine (CHEBI:75240) has functional parent palmitoleic acid (CHEBI:28716)
1-acyl-2-palmitoleoylglycerolipid (CHEBI:87003) has functional parent palmitoleic acid (CHEBI:28716)
1-myristoyl-2-palmitoleoyl-sn-glycero-3-phosphocholine (CHEBI:84578) has functional parent palmitoleic acid (CHEBI:28716)
1-myristoyl-2-palmitoleoyl-sn-glycerol (CHEBI:84386) has functional parent palmitoleic acid (CHEBI:28716)
1-octadecanoyl-2-(9Z)-hexadecenoyl-sn-glycero-3-phosphate (CHEBI:75073) has functional parent palmitoleic acid (CHEBI:28716)
1-octadecanoyl-2-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:86097) has functional parent palmitoleic acid (CHEBI:28716)
1-oleoyl-2-palmitoleoyl-sn-glycero-3-phospho-L-serine (CHEBI:75101) has functional parent palmitoleic acid (CHEBI:28716)
1-oleoyl-2-palmitoleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:82837) has functional parent palmitoleic acid (CHEBI:28716)
1-palmitoleoyl-2-linoleoyl-sn-glycero-3-phosphocholine (CHEBI:84567) has functional parent palmitoleic acid (CHEBI:28716)
1-palmitoleoyl-2-linoleoyl-sn-glycerol (CHEBI:84419) has functional parent palmitoleic acid (CHEBI:28716)
1-palmitoleoyl-2-palmitoyl-sn-glycero-3-phosphocholine (CHEBI:89731) has functional parent palmitoleic acid (CHEBI:28716)
1-palmitoleoyl-2-stearoyl-sn-glycero-3-phosphocholine (CHEBI:84570) has functional parent palmitoleic acid (CHEBI:28716)
1-palmitoleoyl-2-stearoyl-sn-glycerol (CHEBI:84418) has functional parent palmitoleic acid (CHEBI:28716)
1-palmitoleoyl-sn-glycerol 3-phosphate (CHEBI:75070) has functional parent palmitoleic acid (CHEBI:28716)
1-palmitoyl-2-palmitoleoyl-sn-glycero-3-phosphocholine (CHEBI:74000) has functional parent palmitoleic acid (CHEBI:28716)
1-palmitoyl-2-palmitoleoyl-sn-glycerol (CHEBI:84394) has functional parent palmitoleic acid (CHEBI:28716)
1-tetradecyl-2-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:86225) has functional parent palmitoleic acid (CHEBI:28716)
12-[(9Z)-hexadecenoyloxy]octadecanoic acid (CHEBI:137085) has functional parent palmitoleic acid (CHEBI:28716)
13-[(9Z)-hexadecenoyloxy]octadecanoic acid (CHEBI:137086) has functional parent palmitoleic acid (CHEBI:28716)
2,3-dipalmitoleoyl-sn-glycerol (CHEBI:75853) has functional parent palmitoleic acid (CHEBI:28716)
2-[(9Z)-hexadecenoyl]glycerol (CHEBI:87254) has functional parent palmitoleic acid (CHEBI:28716)
2-hydroxypalmitoleic acid (CHEBI:143026) has functional parent palmitoleic acid (CHEBI:28716)
5-[(9Z)-hexadecenoyloxy]octadecanoic acid (CHEBI:137102) has functional parent palmitoleic acid (CHEBI:28716)
9-[(9Z)-hexadecenoyloxy]octadecanoic acid (CHEBI:137084) has functional parent palmitoleic acid (CHEBI:28716)
N-[(9Z)-hexadecenoyl]glycine (CHEBI:136618) has functional parent palmitoleic acid (CHEBI:28716)
[(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:140432) has functional parent palmitoleic acid (CHEBI:28716)
cholesteryl palmitoleate (CHEBI:84323) has functional parent palmitoleic acid (CHEBI:28716)
episteryl palmitoleate (CHEBI:52376) has functional parent palmitoleic acid (CHEBI:28716)
ethyl palmitoleate (CHEBI:84934) has functional parent palmitoleic acid (CHEBI:28716)
lauryl palmitoleate (CHEBI:84155) has functional parent palmitoleic acid (CHEBI:28716)
methyl palmitoleate (CHEBI:84156) has functional parent palmitoleic acid (CHEBI:28716)
palmitoleamide (CHEBI:146162) has functional parent palmitoleic acid (CHEBI:28716)
palmitoleoyl ethanolamide (CHEBI:71465) has functional parent palmitoleic acid (CHEBI:28716)
palmitoleoyl-CoA (CHEBI:53152) has functional parent palmitoleic acid (CHEBI:28716)
palmitoleoyl-containing glycerolipid (CHEBI:88261) has functional parent palmitoleic acid (CHEBI:28716)
palmityl palmitoleate (CHEBI:75629) has functional parent palmitoleic acid (CHEBI:28716)
2-[(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:133515) is a palmitoleic acid (CHEBI:28716)
palmitoleate (CHEBI:32372) is conjugate base of palmitoleic acid (CHEBI:28716)
IUPAC Name
(9Z)-hexadec-9-enoic acid
Synonyms Sources
(9Z)-Hexadecenoic acid KEGG COMPOUND
(Z)-9-hexadecenoic acid ChEBI
(Z)-hexadec-9-enoic acid ChemIDplus
16:1Δ9 ChEBI
9-cis-hexadecenoic acid ChEBI
cis-9-Hexadecenoic acid KEGG COMPOUND
cis-9-Palmitoleic acid HMDB
cis-delta-9-Hexadecenoic acid HMDB
cis-Δ9-hexadecenoic acid ChEBI
cis-Palmitoleic acid HMDB
Oleopalmitic acid HMDB
PALMITOLEIC ACID PDBeChem
Palmitoleic acid KEGG COMPOUND
Palmitoleic acid KEGG COMPOUND
palmitolinoleic acid NIST Chemistry WebBook
zoomaric acid LIPID MAPS
Zoomeric acid HMDB
Manual Xrefs Databases
C00001234 KNApSAcK
C00029354 KNApSAcK
C08362 KEGG COMPOUND
DB04257 DrugBank
HMDB0003229 HMDB
LMFA01030056 LIPID MAPS
PAM PDBeChem
View more database links
Registry Numbers Types Sources
1725389 Reaxys Registry Number Reaxys
1725389 Beilstein Registry Number Beilstein
373-49-9 CAS Registry Number ChemIDplus
373-49-9 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
19761868 PubMed citation Europe PMC
24362891 PubMed citation Europe PMC
Last Modified
23 October 2023
General Comments
2010-04-22 Additional citation (no PMID) -- Kawahara K et al., (1994): Isolation of Sphingomonas Strains from Ears of Rice and Other Plants of Family Gramineae - Biosci. Biotech. Biochem. 58(3): 600-601.
2011-02-07 A non-essential fatty acid with antimicrobial properties, found in various animal, vegetable and marine oils, and a common constituent of glycerides in human adipose tissue.