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CHEBI:28716 - palmitoleic acid

ChEBI IDCHEBI:28716
ChEBI Namepalmitoleic acid
Stars
DefinitionA hexadec-9-enoic acid in which the double bond at position C-9 has cis configuration.
Secondary ChEBI IDsCHEBI:7897, CHEBI:25836, CHEBI:44696
Last Modified23 October 2023
DownloadsMolfile
FormulaC16H30O2
Net Charge0
Average Mass254.414
Monoisotopic Mass254.22458
SMILESCCCCCC/C=C\CCCCCCCC(=O)O
InChIInChI=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-
InChIKeySECPZKHBENQXJG-FPLPWBNLSA-N
Species of MetaboliteComponentSourceComments
Daphnia galeata (ncbitaxon:27404) - Article (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)
Homo sapiens (ncbitaxon:9606) blood serum (BTO:0000133) MetaboLights (MTBLS90)
Chlamydomonas reinhardtii (ncbitaxon:3055) - PubMed (25515814)
Escherichia coli (ncbitaxon:562) - PubMed (21988831)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
Escherichia coli metabolite  Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
human blood serum metabolite  Any metabolite (endogenous or exogenous) found in human blood serum samples.
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 ).
Daphnia galeata metabolite  A Daphnia metabolite produced by the species Daphnia galeata.
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.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
[(9Z)-hexadecenoyl]-sn-glycero-3-phosphocholine (CHEBI:140432) has functional parent palmitoleic acid (CHEBI:28716)
N-[(9Z)-hexadecenoyl]glycine (CHEBI:136618) 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]-sn-glycero-3-phosphocholine (CHEBI:73851) 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]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-sn-glycerol 3-phosphate (CHEBI:75070) 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-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)
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)
1,2,3-tripalmitoleoylglycerol (CHEBI:75841) has functional parent palmitoleic acid (CHEBI:28716)
1,3-dipalmitoleoylglycerol (CHEBI:75849) 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-[(9Z)-hexadecenoyl]glycerol (CHEBI:87254) has functional parent palmitoleic acid (CHEBI:28716)
2-hydroxypalmitoleic acid (CHEBI:143026) has functional parent palmitoleic acid (CHEBI:28716)
2,3-dipalmitoleoyl-sn-glycerol (CHEBI:75853) 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)
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  Source
Palmitoleic acidKEGG COMPOUND
cis-9-Hexadecenoic acidKEGG COMPOUND
(Z)-hexadec-9-enoic acidChemIDplus
palmitolinoleic acidNIST Chemistry WebBook
PALMITOLEIC ACIDPDBeChem
cis-Δ9-hexadecenoic acidChEBI
Manual XrefsDatabases
C08362KEGG COMPOUND
PAMPDBeChem
LMFA01030056LIPID MAPS
DB04257DrugBank
C00029354KNApSAcK
C00001234KNApSAcK
HMDB0003229HMDB
Registry NumbersSources
Reaxys:1725389Reaxys
CAS:373-49-9KEGG COMPOUND
CAS:373-49-9ChemIDplus
CAS:373-49-9NIST Chemistry WebBook
Citations