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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2017-08-01 02:13:26 UTC
Update Date2020-06-15 17:04:53 UTC
HMDB IDHMDB0094656
Secondary Accession Numbers
  • HMDB94656
Metabolite Identification
Common Name2-Hydroxydecanoate
Description2-Hydroxydecanoate (CAS: 5393-81-7), also known as alpha-hydroxycapric acid, is classified as a member of the medium-chain fatty acids. Medium-chain fatty acids are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. 2-Hydroxydecanoate is considered to be a practically insoluble (in water) and a weakly acidic compound. 2-Hydroxydecanoate can be found in feces.
Structure
Data?1571765969
Synonyms
ValueSource
2S-Hydroxy-decanoateGenerator
(2S)-2-HydroxydecanoateHMDB
(2S)-2-Hydroxydecanoic acidHMDB
(S)-2-HydroxydecanoateHMDB
(S)-2-Hydroxydecanoic acidHMDB
(S)-alpha-HydroxycaprateHMDB
(S)-alpha-Hydroxycapric acidHMDB
(S)-alpha-HydroxydecanoateHMDB
(S)-alpha-Hydroxydecanoic acidHMDB
(S)-α-HydroxycaprateHMDB
(S)-α-Hydroxycapric acidHMDB
(S)-α-HydroxydecanoateHMDB
(S)-α-Hydroxydecanoic acidHMDB
(±)-2-HydroxydecanoateHMDB
(±)-2-Hydroxydecanoic acidHMDB
(±)-alpha-HydroxycaprateHMDB
(±)-alpha-Hydroxycapric acidHMDB
(±)-alpha-HydroxydecanoateHMDB
(±)-alpha-Hydroxydecanoic acidHMDB
(±)-α-HydroxycaprateHMDB
(±)-α-Hydroxycapric acidHMDB
(±)-α-HydroxydecanoateHMDB
(±)-α-Hydroxydecanoic acidHMDB
2-HydroxycaprateHMDB
2-Hydroxycapric acidHMDB
2-HydroxydecanoateHMDB
2-Hydroxydecanoic acidHMDB
DL-2-HydroxycaprateHMDB
DL-2-Hydroxycapric acidHMDB
FA(10:0(2-OH))HMDB
FA(10:0(2S-OH))HMDB
alpha-HydroxycaprateHMDB
alpha-Hydroxycapric acidHMDB
alpha-HydroxydecanoateHMDB
alpha-Hydroxydecanoic acidHMDB
α-HydroxycaprateHMDB
α-Hydroxycapric acidHMDB
α-HydroxydecanoateHMDB
α-Hydroxydecanoic acidHMDB
Chemical FormulaC10H20O3
Average Molecular Weight188.267
Monoisotopic Molecular Weight188.141244504
IUPAC Name(2S)-2-hydroxydecanoic acid
Traditional Namel-2-hydroxydecanoic acid
CAS Registry Number70267-29-7
SMILES
CCCCCCCC[C@H](O)C(O)=O
InChI Identifier
InChI=1S/C10H20O3/c1-2-3-4-5-6-7-8-9(11)10(12)13/h9,11H,2-8H2,1H3,(H,12,13)/t9-/m0/s1
InChI KeyGHPVDCPCKSNJDR-VIFPVBQESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.93ALOGPS
logP2.72ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4.26ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity50.97 m³·mol⁻¹ChemAxon
Polarizability22.39 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5312797
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.