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Record Information
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.
(9Z)-Hexadecenoic acidChEBI
(Z)-9-Hexadecenoic acidChEBI
(Z)-Hexadec-9-enoic acidChEBI
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
cis-Δ-9-hexadecenoic acidGenerator
cis-Δ(9)-hexadecenoic acidGenerator
(9Z)-Hexadec-9-enoic acidGenerator
9-Hexadecenoic acidHMDB
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
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
InChI Identifier
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species of Origin
Species NameSourceReference
Abelmoschus esculentusLOTUS Database
Abies pinsapoLOTUS Database
Abutilon ramosumLOTUS Database
Acorus calamusLOTUS Database
Aesculus hippocastanumLOTUS Database
Agaricus blazeiLOTUS Database
Agave decipiensLOTUS Database
Agelas coniferaLOTUS Database
Agrimonia pilosaLOTUS Database
Alchemilla pentaphylleaLOTUS Database
Allamanda catharticaLOTUS Database
Allium hirtifoliumPlant
Aloe vera var.chinensisKNApSAcK Database
Alpinia oxyphyllaKNApSAcK Database
Amaranthus caudatusLOTUS Database
Anas platyrhynchosFooDB
Anethum graveolensLOTUS Database
Anisophyllea laurinaLOTUS Database
Anser anserFooDB
Apis ceranaLOTUS Database
Aquilaria sinensisLOTUS Database
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Arnica montanaLOTUS Database
Asclepias syriacaLOTUS Database
Astragalus hamosusLOTUS Database
Bellis perennisLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica hirtaKNApSAcK Database
Bryonia albaLOTUS Database
Bubalus bubalisFooDB
Cachrys siculaLOTUS Database
Callyspongia fallaxLOTUS Database
Calophyllum inophyllumKNApSAcK Database
Calopyllum calaba-
Canavalia ensiformisLOTUS Database
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
Carica papayaLOTUS Database
Carica papaya L.FooDB
Cassia fistulaLOTUS Database
Cervicornia cuspidiferaLOTUS Database
Cervus canadensisFooDB
Chlamydomonas reinhardtiiLOTUS Database
Citrullus colocynthisLOTUS Database
Cleistanthus collinusLOTUS Database
Cucumis meloFooDB
Curcuma longaLOTUS Database
Dermochelys coriaceaLOTUS Database
Dictamnus albusLOTUS Database
Dromaius novaehollandiaeFooDB
Dryopteris carthusianaLOTUS Database
Echinacea purpureaLOTUS Database
Elaeagnus angustifoliaLOTUS Database
Elaeis guineensisKNApSAcK Database
Epilobium parviflorumLOTUS Database
Equus caballusFooDB
Erigeron caucasicusLOTUS Database
Fagopyrum esculentumFooDB
Festuca rubraLOTUS Database
Fumaria vaillantiiLOTUS Database
Gallus gallusFooDB
Ganoderma australeLOTUS Database
Garcinia xanthochymusLOTUS Database
Gossypium hirsutumLOTUS Database
Hibiscus cannabinusLOTUS Database
Hippophae rhamnoidesKNApSAcK Database
Hypericum maculatumLOTUS Database
Inula grandisLOTUS Database
Isatis tinctoriaKNApSAcK Database
Jodina rhombifoliaLOTUS Database
Juglans nigra L.FooDB
Lactuca saligna L.LOTUS Database
Lagopus mutaFooDB
Laminaria japonicaKNApSAcK Database
Lepidium meyeniiLOTUS Database
Leptolyngbya tenuisLOTUS Database
Lepus timidusFooDB
Macadamia integrifoliaLOTUS Database
Macadamia ternifoliaKNApSAcK Database
Mangifera indicaKNApSAcK Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mentha spicataLOTUS Database
Mitracarpus hirtusLOTUS Database
Momordica charantiaLOTUS Database
Moquilea tomentosaLOTUS Database
Mucuna puriensPlant
Musa paradisiacaLOTUS Database
Mycale laevisLOTUS Database
Myrmekioderma reaLOTUS Database
Nigella sativaLOTUS Database
Numida meleagrisFooDB
Nymphaea albaKNApSAcK Database
Oecophylla smaragdinaLOTUS Database
Oenothera biennisLOTUS Database
Olea europaeaLOTUS Database
Oncophorus crispifoliusLOTUS Database
Ovis ariesFooDB
Penicillium oxalicumLOTUS Database
Petroselinum crispumFooDB
Phaseolus coccineusLOTUS Database
Phasianus colchicusFooDB
Pinus radiataLOTUS Database
Pinus sibiricaPlant
Pistacia veraLOTUS Database
Portulaca oleraceaLOTUS Database
Proiphys amboinensisLOTUS Database
Prunus armeniacaKNApSAcK Database
Pseudo-nitzschia multistriataLOTUS Database
Pterodon emarginatusLOTUS Database
Punica granatumKNApSAcK Database
Rehmannia glutinosaKNApSAcK Database
Sabal minorLOTUS Database
Saccharina japonicaPlant
Salmonella entericaLOTUS Database
Salpa thompsoniLOTUS Database
Scomber japonicusLOTUS Database
Sesamum indicumFooDB
Sideritis tauricaLOTUS Database
Sinapis albaPlant
Sinopodophyllum hexandrumLOTUS Database
Smenospongia aureaLOTUS Database
Stellaria dichotomaLOTUS Database
Sterculia foetidaLOTUS Database
Sterculia tragacanthaLOTUS Database
Struthio camelusFooDB
Stuckenia pectinataLOTUS Database
Suaeda aegyptiacaLOTUS Database
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Talaromyces flavusLOTUS Database
Taonia atomariaLOTUS Database
Taraxacum officinaleFooDB
Tilia cordataPlant
Tilia cordata Mill.KNApSAcK Database
Treculia africanaLOTUS Database
Trichosanthes kirilowiiKNApSAcK Database
Trichosanthes rosthorniiKNApSAcK Database
Trifolium alexandrinumLOTUS Database
Tripneustes ventricosusLOTUS Database
Trypanosoma bruceiLOTUS Database
Turnera ulmifoliaLOTUS Database
Vitex trifoliaKNApSAcK Database
Xestospongia mutaLOTUS 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
  • 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
Experimental Properties
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
Water Solubility0.00045 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
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
DrugBank IDDB04257
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031085
KNApSAcK IDC00001234
Chemspider ID393216
KEGG Compound IDC08362
BioCyc IDCPD-9245
BiGG ID246167
Wikipedia LinkPalmitoleic acid
PubChem Compound445638
PDB IDNot Available
ChEBI ID28716
Good Scents IDrw1271951
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 ]