palmitoleate (PAMDB120366)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120366
Identification
Name: palmitoleate
Description:A hexadec-9-enoate that is the conjugate base of palmitoleic acid; major species at pH 7.3.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (16:1n7)
  • (9Z)-hexadecenoate
  • (Z)-9-hexadecenoate
  • (Z)-hexadec-9-enoate
  • 9-cis-hexadecenoate
  • cis-9-hexadecenoate
  • cis-Δ9-hexadecenoate
  • palmitolinoleate
  • zoomarate
Chemical Formula: C16H29O2
Average Molecular Weight: 253.404
Monoisotopic Molecular Weight: 254.22458
InChI Key: SECPZKHBENQXJG-FPLPWBNLSA-M
InChI: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)/p-1/b8-7-
CAS number: 373-49-9
IUPAC Name:(9Z)-hexadec-9-enoate
Traditional IUPAC Name: palmitoleic acid
SMILES:CCCCCCC=CCCCCCCCC(=O)[O-]
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Lipids and lipid-like molecules
Sub ClassFatty Acyls
Direct Parent Long-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 Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Liquid
Charge:-1
Melting point: -0.1 °C
Experimental Properties:
PropertyValueReference
Melting Point-0.1 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.000447 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity78.2 m3·mol-1ChemAxon
Polarizability32.87 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Water → palmitoleate + Hydrogen ion
Pathways:
  • superpathway of unsaturated fatty acids biosynthesis (E. coli)PWY-6284
  • palmitoleate biosynthesis IIPWY-5366
  • palmitoleate biosynthesis IPWY-6282
  • superpathway of fatty acids biosynthesis (E. coli)PWY-6285
    Spectra
    Spectra:
    Spectrum TypeDescriptionSplash Key
    GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00nb-5900000000-90ab9a21246ad658bda0View in MoNA
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0090000000-202819132f83589a248bView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4s-7790000000-ff129e0c7cc2a7e4cf19View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9600000000-749f09fec19d95c21683View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-5005f244d7d1c3502c3eView in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zg0-1090000000-cac7fce9a75b0f1abd63View in MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9320000000-2e782c63ccf72afe9be9View in MoNA
    1D NMR1H NMR SpectrumNot Available
    1D NMR13C NMR SpectrumNot Available
    References
    References:
    • 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. [19212411 ]
    • 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. [15854043 ]
    • 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. [2583914 ]
    • 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. [12217898 ]
    • 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. [9547901 ]
    • 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. [11297913 ]
    • Prandota J: Clinical pharmacology of antibiotics and other drugs in cystic fibrosis. Drugs. 1988 May;35(5):542-78. [3293970 ]
    • 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 Mar 3. doi: 10.1038/nbt.2488. [23455439 ]
    Synthesis Reference: Xu, Huashun; Luo, Yuping; Li, Siguang. Palmitoleic acid production by fermentation with yeast. Zhongguo Youzhi (1999), 24(6), 53-55.
    Material Safety Data Sheet (MSDS) Download (PDF)
    External Links:
    ResourceLink
    METABOLIGHTSMTBLC32372
    HMDBHMDB03229
    CHEMSPIDER4574392
    LIGAND-CPDC08362
    CAS373-49-9
    PUBCHEM5461012
    CHEBI32372