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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-11-30 15:50:58 UTC
Update Date2020-02-27 16:51:54 UTC
HMDB IDHMDB0013207
Secondary Accession Numbers
  • HMDB13207
Metabolite Identification
Common Name9-Hexadecenoylcarnitine
Description9-Hexadecenoylcarnitine, also known as palmitoleoylcarnitine, is considered to be a practically insoluble (in water) and a weak acidic compound. 9-hexadecenoylcarnitine can be found in blood. Within a cell, 9-hexadecenoylcarnitine is primarily located in the extracellular space and near the membrane. This compound belongs to the class of chemical entities known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. 9-Hexadecenoylcarnitine is found to be associated with glutaric aciduria II, which is an inborn error of metabolism.
Structure
Data?1582753100
Synonyms
ValueSource
(3R)-3-[(9Z)-Hexadec-9-enoyloxy]-4-(trimethylazaniumyl)butanoic acidGenerator
9-HexadecenoylcarnitineHMDB
PalmitoleoylcarnitineHMDB
Chemical FormulaC23H43NO4
Average Molecular Weight397.6
Monoisotopic Molecular Weight397.319208869
IUPAC Name(3R)-3-[(9Z)-hexadec-9-enoyloxy]-4-(trimethylazaniumyl)butanoate
Traditional Name(3R)-3-[(9Z)-hexadec-9-enoyloxy]-4-(trimethylammonio)butanoate
CAS Registry Number329321-94-0
SMILES
CCCCCC\C=C/CCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C23H43NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4/h10-11,21H,5-9,12-20H2,1-4H3/b11-10-/t21-/m1/s1
InChI KeyJFAGPSOZZSTLRF-KUFMOJEASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentAcyl carnitines
Alternative Parents
Substituents
  • Acyl-carnitine
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid salt
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility9.9e-06 g/LALOGPS
logP1.03ALOGPS
logP1.67ChemAxon
logS-7.7ALOGPS
pKa (Strongest Acidic)4.22ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity138.19 m³·mol⁻¹ChemAxon
Polarizability48.83 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.03 +/- 0.01 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.010-0.060 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.03 +/- 0.01 uMChildren (1-13 years old)BothNormal details
BloodDetected and Quantified<0.08 uMAdolescent (13-18 years old)MaleNormal details
FecesDetected and Quantified0.29 +/- 0.16 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0.25 +/- 0.11 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0-0.03 umol/mmol creatinineNewborn (0-30 days old)BothNormal
    • López Hernández Y...
details
UrineDetected and Quantified0.01 +/- 0.01 umol/mmol creatinineNewborn (0-30 days old)FemaleNormal
    • López Hernández Y...
details
UrineDetected and Quantified0.01 +/- 0.0 umol/mmol creatinineNewborn (0-30 days old)MaleNormal
    • López Hernández Y...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.04 +/- 0.01 uMChildren (1-13 years old)Both
Obese
details
BloodDetected and Quantified0.04 +/- 0.01 uMChildren (1-13 years old)Both
Obese
details
BloodDetected and Quantified0.04 +/- 0.01 uMChildren (1-13 years old)Both
Obese
details
BloodDetected and Quantified0.041 +/- 0.012 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified0.044 +/- 0.013 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified0.04 +/- 0.01 uMChildren (1-13 years old)Both
Obese
details
BloodDetected and Quantified0.33 uMAdolescent (13-18 years old)Male
Glutaric aciduria II
details
BloodDetected and Quantified0.9 uMAdolescent (13-18 years old)MaleGlutaric aciduria II details
Associated Disorders and Diseases
Disease References
Glutaric aciduria II
  1. Prasad M, Hussain S: Glutaric aciduria type II presenting as myopathy and rhabdomyolysis in a teenager. J Child Neurol. 2015 Jan;30(1):96-9. doi: 10.1177/0883073813516676. Epub 2014 Jan 21. [PubMed:24453145 ]
Obesity
  1. Reinehr T, Wolters B, Knop C, Lass N, Hellmuth C, Harder U, Peissner W, Wahl S, Grallert H, Adamski J, Illig T, Prehn C, Yu Z, Wang-Sattler R, Koletzko B: Changes in the serum metabolite profile in obese children with weight loss. Eur J Nutr. 2015 Mar;54(2):173-81. doi: 10.1007/s00394-014-0698-8. Epub 2014 Apr 17. [PubMed:24740590 ]
  2. Wahl S, Yu Z, Kleber M, Singmann P, Holzapfel C, He Y, Mittelstrass K, Polonikov A, Prehn C, Romisch-Margl W, Adamski J, Suhre K, Grallert H, Illig T, Wang-Sattler R, Reinehr T: Childhood obesity is associated with changes in the serum metabolite profile. Obes Facts. 2012;5(5):660-70. doi: 10.1159/000343204. Epub 2012 Oct 4. [PubMed:23108202 ]
  3. Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID28639183
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.