Showing Compound Card for Palmitoleic acid (CDB000052)

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Record Information
Version1.0
Created at2020-03-18 23:23:00 UTC
Updated at2020-12-07 19:07:01 UTC
CannabisDB IDCDB000052
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NamePalmitoleic acid
DescriptionPalmitoleic acid, also known as palmitoleate or zoomaric acid or C16:1, is an omega-7 monounsaturated fatty acid that is found in plants (PMID: 11308350 ) such as cannabis plants (PMID:6991645 ) and marine sources (PMID: 19382347 ). It belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Palmitoleic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Palmitoleic acid exists in all living species, ranging from bacteria to humans. Macadamia nuts and buckthorn seed oil contain the cis isomer of palmitoleic acid. Palmitoleic acid is also found in mung beans, java plums, napa cabbages, cucurbita (gourd), and kiwis.. It is also a common constituent of the glycerides of human adipose tissue. Present in all tissues, it is generally found in higher concentrations in the liver. Palmitoleic acid, with regard to humans, has been found to be associated with several diseases such as colorectal cancer and cirrhosis; palmitoleic acid has also been linked to the inborn metabolic disorder isovaleric acidemia. Palmitoleic acid has been reported to have beneficial effects on insulin sensitivity, cholesterol metabolism, and hemostasis. Other positive effects reported include lowering LDL cholesterol and increasing high-density lipoprotein cholesterol (HDL)( Ref:DOI ). Palmitoleic acid is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(9Z)-Hexadecenoic acidChEBI
(Z)-9-Hexadecenoic acidChEBI
(Z)-Hexadec-9-enoic acidChEBI
16:1DElta9ChEBI
9-cis-Hexadecenoic acidChEBI
cis-9-Hexadecenoic acidChEBI
cis-9-Palmitoleic acidChEBI
cis-delta-9-Hexadecenoic acidChEBI
cis-Delta(9)-Hexadecenoic acidChEBI
cis-Palmitoleic acidChEBI
Oleopalmitic acidChEBI
Palmitolinoleic acidChEBI
Zoomaric acidChEBI
Zoomeric acidChEBI
(9Z)-Hexadec-9-enoateKegg
(9Z)-HexadecenoateGenerator
(Z)-9-HexadecenoateGenerator
(Z)-Hexadec-9-enoateGenerator
9-cis-HexadecenoateGenerator
cis-9-HexadecenoateGenerator
cis-9-PalmitoleateGenerator
cis-delta-9-HexadecenoateGenerator
cis-Δ-9-hexadecenoateGenerator
cis-Δ-9-hexadecenoic acidGenerator
cis-delta(9)-HexadecenoateGenerator
cis-Δ(9)-hexadecenoateGenerator
cis-Δ(9)-hexadecenoic acidGenerator
cis-PalmitoleateGenerator
OleopalmitateGenerator
PalmitolinoleateGenerator
ZoomarateGenerator
ZoomerateGenerator
(9Z)-Hexadec-9-enoic acidGenerator
PalmitoleateGenerator
9-HexadecenoateHMDB
9-Hexadecenoic acidHMDB
HexadecenoateHMDB
Hexadecenoate (N-C16:1)HMDB
Hexadecenoic acidHMDB
Palmitoleic acid, (Z)-isomerHMDB
Palmitoleic acid, (e)-isomerHMDB
C16:1 trans-9HMDB
Palmitelaidic acidHMDB
(9Z)-9-Hexadecenoic acidHMDB
9Z-Hexadecenoic acidHMDB
C16:1HMDB
FA(16:1(9Z))HMDB
FA(16:1n7)HMDB
cis-delta9-Hexadecenoic acidHMDB
cis-Δ9-hexadecenoic acidHMDB
Palmitoleic acidHMDB
Chemical FormulaC16H30O2
Average Molecular Weight254.41
Monoisotopic Molecular Weight254.2246
IUPAC Name(9Z)-hexadec-9-enoic acid
Traditional Namepalmitoleic acid
CAS Registry Number373-49-9
SMILES
CCCCCC\C=C/CCCCCCCC(O)=O
InChI Identifier
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-
InChI KeySECPZKHBENQXJG-FPLPWBNLSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-0.1 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.71ALOGPS
logP5.89ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity78.2 m³·mol⁻¹ChemAxon
Polarizability32.87 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSPalmitoleic acid, 1 TMS, GC-MS Spectrumsplash10-00nb-5900000000-90ab9a21246ad658bda0Spectrum
GC-MSPalmitoleic acid, non-derivatized, GC-MS Spectrumsplash10-00mk-2900000000-6683cd8579813b4f1ebbSpectrum
GC-MSPalmitoleic acid, non-derivatized, GC-MS Spectrumsplash10-00nb-5900000000-90ab9a21246ad658bda0Spectrum
GC-MSPalmitoleic acid, non-derivatized, GC-MS Spectrumsplash10-00nb-5900000000-90ab9a21246ad658bda0Spectrum
Predicted GC-MSPalmitoleic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-8910000000-20fcd1fc2d9e095b2c24Spectrum
Predicted GC-MSPalmitoleic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00fr-9630000000-7eda678c0ecd65b2e479Spectrum
Predicted GC-MSPalmitoleic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPalmitoleic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac3592017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac3592017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0092000000-b8aabbdc61f9b89ac3592017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0090000000-993c95f96e1ca69a41c02017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0090000000-e72ac58f23bacbf373442017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0090000000-d1585cc46cbce84a05062017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0udi-0091000000-fd89101236e85a2d91542017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0090000000-35027c88ff732ff74b4c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0090000000-3cac469ac1efde0a35432017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0090000000-e5833c7aa4795570bdc42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-9090000000-909ebad9120d01bf8e792017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9000000000-fb5a2e21c48a7d72aac82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0udi-0090000000-09c91b61deabc72625f32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0090000000-993c95f96e1ca69a41c02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0090000000-e72ac58f23bacbf373442017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 17V, positivesplash10-000i-0490000000-472e6cf8ba7a80f708b82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0a4i-0090000000-3c6c13dcd5649fd908452020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0a4i-0090000000-e5cccbc8340bb0dce9d32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0a4i-2490000000-1dbd141e66d6e7a165ae2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0090000000-202819132f83589a248b2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4s-7790000000-ff129e0c7cc2a7e4cf192015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9600000000-749f09fec19d95c216832015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-5005f244d7d1c3502c3e2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zg0-1090000000-cac7fce9a75b0f1abd632015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9320000000-2e782c63ccf72afe9be92015-09-15View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
S-acyl fatty acid synthase thioesterase, medium chainOLAH10p13Q9NV23 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0003229
DrugBank IDDB04257
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031085
KNApSAcK IDC00001234
Chemspider ID393216
KEGG Compound IDC08362
BioCyc IDCPD-9245
BiGG ID246167
Wikipedia LinkPalmitoleic acid
METLIN ID188
PubChem Compound445638
PDB IDNot Available
ChEBI ID28716
References
General References
  1. Yang B, Kallio HP: Fatty acid composition of lipids in sea buckthorn (Hippophae rhamnoides L.) berries of different origins. J Agric Food Chem. 2001 Apr;49(4):1939-47. doi: 10.1021/jf001059s. [PubMed:11308350 ]
  2. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  3. Polat S, Ozogul Y: Biochemical composition of some red and brown macro algae from the Northeastern Mediterranean Sea. Int J Food Sci Nutr. 2008 Nov-Dec;59(7-8):566-72. doi: 10.1080/09637480701446524. [PubMed:19382347 ]

Enzymes

Enzyme Details
1. S-acyl fatty acid synthase thioesterase, medium chain
General function:
Involved in biosynthetic process
Specific function:
In fatty acid biosynthesis chain termination and release of the free fatty acid product is achieved by hydrolysis of the thio ester by a thioesterase I, a component of the fatty acid synthetase complex. The chain length of the released fatty acid is usually C16. However, in the mammary glands of non-ruminant mammals, and in the uropygial gland of certain waterfowl there exists a second thioesterase which releases medium-chain length fatty acids (C8 to C2) (By similarity).
Gene Name:
OLAH
Uniprot ID:
Q9NV23
Molecular weight:
29930.82