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CHEBI:28716 - palmitoleic acid

Default Structure
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
Chlamydomonas reinhardtii (ncbitaxon:3055) - PubMed (25515814)
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)
Escherichia coli (ncbitaxon:562) - PubMed (21988831)
Homo sapiens (ncbitaxon:9606) blood serum (BTO:0000133) MetaboLights (MTBLS90)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
Daphnia galeata metabolite  A Daphnia metabolite produced by the species Daphnia galeata.
Escherichia coli metabolite  Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
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.
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
16:1Δ9ChEBI
9-cis-hexadecenoic acidChEBI
(9Z)-Hexadecenoic acidKEGG COMPOUND
cis-9-Hexadecenoic acidKEGG COMPOUND
cis-9-Palmitoleic acidHMDB
cis-delta-9-Hexadecenoic acidHMDB
Manual XrefsDatabases
C00001234KNApSAcK
C00029354KNApSAcK
C08362KEGG COMPOUND
DB04257DrugBank
HMDB0003229HMDB
LMFA01030056LIPID MAPS
PAMPDBeChem
Registry NumbersSources
Reaxys:1725389Reaxys
CAS:373-49-9KEGG COMPOUND
CAS:373-49-9ChemIDplus
CAS:373-49-9NIST Chemistry WebBook
Citations