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Record Information
Version3.6
Creation Date2006-05-22 15:12:43 UTC
Update Date2016-02-11 01:06:07 UTC
HMDB IDHMDB03229
Secondary Accession Numbers
  • HMDB60082
Metabolite Identification
Common NamePalmitoleic acid
Descriptionfatty acids, Monounsaturated. Palmitoleic acid, or 9-hexadecenoic acid, is an unsaturated fatty acid that is a common constituent of the glycerides of human adipose tissue. Present in all tissues, 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. -- Wikipedia.
Structure
Thumb
Synonyms
ValueSource
(9Z)-Hexadecenoic acidChEBI
(Z)-9-Hexadecenoic acidChEBI
16:1DElta9ChEBI
9-cis-Hexadecenoic acidChEBI
cis-9-Hexadecenoic acidChEBI
cis-Delta(9)-Hexadecenoic acidChEBI
Palmitolinoleic acidChEBI
Zoomaric acidChEBI
(9Z)-HexadecenoateGenerator
(Z)-Hexadec-9-enoateGenerator
(Z)-9-HexadecenoateGenerator
9-cis-HexadecenoateGenerator
cis-9-HexadecenoateGenerator
cis-delta(9)-HexadecenoateGenerator
cis-δ(9)-hexadecenoateGenerator
cis-δ(9)-hexadecenoic acidGenerator
PalmitolinoleateGenerator
ZoomarateGenerator
9-HexadecenoateHMDB
9-Hexadecenoic acidHMDB
cis-9-Palmitoleic acidHMDB
cis-delta-9-HexadecenoateHMDB
cis-delta-9-Hexadecenoic acidHMDB
cis-PalmitoleateHMDB
cis-Palmitoleic acidHMDB
HexadecenoateHMDB
Hexadecenoate (N-C16:1)HMDB
Hexadecenoic acidHMDB
OleopalmitateHMDB
Oleopalmitic acidHMDB
PalmitoleateHMDB
ZoomerateHMDB
Zoomeric acidHMDB
Chemical FormulaC16H30O2
Average Molecular Weight254.4082
Monoisotopic Molecular Weight254.224580204
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 KeyInChIKey=SECPZKHBENQXJG-FPLPWBNLSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateLiquid
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00nb-5900000000-90ab9a21246ad658bda0View in MoNA
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
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Adipose Tissue
  • Prostate
  • Skeletal Muscle
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified31.0 (5.0-85.0) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified9.66 +/- 6.8 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified6.390 +/- 4.279 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified4.5 +/- 2.8 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified14.7 +/- 0.169 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.0 +/- 2.0 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2 uMChildren (1-13 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Both
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.8 (0.7-6.6) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.03 +/- 0.02 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04257
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB011675
KNApSAcK IDC00029354
Chemspider ID393216
KEGG Compound IDC08362
BioCyc IDCPD-724
BiGG ID246167
Wikipedia LinkPalmitoleic acid
NuGOwiki LinkHMDB03229
Metagene LinkHMDB03229
METLIN ID188
PubChem Compound445638
PDB IDPAM
ChEBI ID28716
References
Synthesis ReferenceXu, 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)
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. [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. [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. [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. [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. [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. [11297913 ]
  7. Prandota J: Clinical pharmacology of antibiotics and other drugs in cystic fibrosis. Drugs. 1988 May;35(5):542-78. [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 Mar 3. doi: 10.1038/nbt.2488. [23455439 ]

Enzymes

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