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Record Information
Version1.0
Created at2006-05-22 15:12:43 UTC
Updated at2021-08-19 23:58:49 UTC
NP-MRD IDNP0001123
Secondary Accession NumbersNone
Natural Product Identification
Common NamePalmitoleic acid
DescriptionPalmitoleic acid, or (9Z)-hexadec-9-enoic acid, is an omega-7 monounsaturated fatty acid (16:1N-7) with the formula CH3(CH2)5CH=CH(CH2)7COOH that is a common constituent of the glycerides of human adipose tissue. Present in all tissues, it is generally found in higher concentrations in the liver. Macadamia oil (Macadamia integrifolia) and sea buckthorn oil (Hippophae rhamnoides) are botanical sources of palmitoleic acid, containing 22 and 40% respectively. Palmitoleic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism.
Structure
Thumb
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 Mass254.4082 Da
Monoisotopic Mass254.22458 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Aloe vera var.chinensisKNApSAcK Database
Alpinia oxyphyllaKNApSAcK Database
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Brassica hirtaKNApSAcK Database
Calophyllum inophyllumKNApSAcK Database
Cannabis sativaCannabisDB
      Not Available
Carica papaya L.FooDB
Cucumis meloFooDB
Elaeis guineensisKNApSAcK Database
Fagopyrum esculentumFooDB
Hippophae rhamnoidesKNApSAcK Database
Isatis tinctoriaKNApSAcK Database
Juglans nigra L.FooDB
Laminaria japonicaKNApSAcK Database
Macadamia ternifoliaKNApSAcK Database
Mangifera indicaKNApSAcK Database
Nymphaea albaKNApSAcK Database
Petroselinum crispumFooDB
Prunus armeniacaKNApSAcK Database
Punica granatumKNApSAcK Database
Rehmannia glutinosaKNApSAcK Database
Sesamum indicumFooDB
Taraxacum officinaleFooDB
Tilia cordata Mill.KNApSAcK Database
Trichosanthes kirilowiiKNApSAcK Database
Trichosanthes rosthorniiKNApSAcK Database
Vitex trifoliaKNApSAcK Database
Zea mays L.FooDB
Species Where Detected
Species NameSourceReference
Homo sapiens (Serum)KNApSAcK Database
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
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-0.1 °CNot Available
Boiling Point363.00 to 364.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.13 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP6.402 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility0.00045 g/LALOGPS
logP10(6.71) g/LALOGPS
logP10(5.89) g/LChemAxon
logS10(-5.8) g/LALOGPS
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
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
Good Scents IDrw1271951
References
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Katsuta Y, Iida T, Inomata S, Denda M: Unsaturated fatty acids induce calcium influx into keratinocytes and cause abnormal differentiation of epidermis. J Invest Dermatol. 2005 May;124(5):1008-13. [PubMed:15854043 ]
  3. Rossner S, Walldius G, Bjorvell H: Fatty acid composition in serum lipids and adipose tissue in severe obesity before and after six weeks of weight loss. Int J Obes. 1989;13(5):603-12. [PubMed:2583914 ]
  4. Ho RC, Davy KP, Hickey MS, Summers SA, Melby CL: Behavioral, metabolic, and molecular correlates of lower insulin sensitivity in Mexican-Americans. Am J Physiol Endocrinol Metab. 2002 Oct;283(4):E799-808. [PubMed:12217898 ]
  5. Hori Y, Nakamura K, Yamamoto M, Shimada K, Nakadaira H, Shibuya N, Endoh K, Ogoshi K: Determination of free fatty acids in human bile by high-performance liquid chromatography. Ann Clin Biochem. 1998 Mar;35 ( Pt 2):279-82. [PubMed:9547901 ]
  6. Yli-Jama P, Haugen TS, Rebnord HM, Ringstad J, Pedersen JI: Selective mobilisation of fatty acids from human adipose tissue. Eur J Intern Med. 2001 Apr;12(2):107-115. [PubMed:11297913 ]
  7. Prandota J: Clinical pharmacology of antibiotics and other drugs in cystic fibrosis. Drugs. 1988 May;35(5):542-78. [PubMed:3293970 ]
  8. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]