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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:19:27 UTC
HMDB IDHMDB0000711
Secondary Accession Numbers
  • HMDB00711
Metabolite Identification
Common NameHydroxyoctanoic acid
DescriptionHydroxyoctanoic acid medium chain substrate of the 2-hydroxy acid oxidases associated with the 3 distinct human 2-hydroxy acid oxidase genes, HAOX1, HAOX2, and HAOX3. (PMID: 10777549 ).
Structure
Thumb
Synonyms
ValueSource
2-Hydroxycaprylic acidChEBI
alpha-Hydroxyoctanoic acidChEBI
2-HydroxycaprylateGenerator
HydroxyoctanoateGenerator
a-HydroxyoctanoateGenerator
a-Hydroxyoctanoic acidGenerator
alpha-HydroxyoctanoateGenerator
α-hydroxyoctanoateGenerator
α-hydroxyoctanoic acidGenerator
2-HydroxyoctanoateHMDB
2-Hydroxyoctanoic acidHMDB
a-Hydroxy-N-caprylateHMDB
a-Hydroxy-N-caprylic acidHMDB
a-HydroxycaprylateHMDB
a-Hydroxycaprylic acidHMDB
alpha-Hydroxy-N-caprylateHMDB
alpha-Hydroxy-N-caprylic acidHMDB
alpha-HydroxycaprylateHMDB
alpha-Hydroxycaprylic acidHMDB
DL-2-HydroxycaprylateHMDB
DL-2-Hydroxycaprylic acidHMDB
DL-2-HydroxyoctanoateHMDB
DL-2-Hydroxyoctanoic acidHMDB
alpha-HCA acidMeSH
Chemical FormulaC8H16O3
Average Molecular Weight160.2108
Monoisotopic Molecular Weight160.109944378
IUPAC Name2-hydroxyoctanoic acid
Traditional Namehydroxyoctanoate
CAS Registry Number617-73-2
SMILES
CCCCCCC(O)C(O)=O
InChI Identifier
InChI=1S/C8H16O3/c1-2-3-4-5-6-7(9)8(10)11/h7,9H,2-6H2,1H3,(H,10,11)
InChI KeyJKRDADVRIYVCCY-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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

Biological Location:

  Biofluid and excreta:

  Subcellular:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point70 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility927 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility11.2 g/LALOGPS
logP1.8ALOGPS
logP1.83ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)4.42ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity41.77 m³·mol⁻¹ChemAxon
Polarizability18.01 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-890554b11e06b21369e8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00kr-9140000000-3722662911cf632a3db8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-0900000000-274854495f347923df57View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-01ot-9600000000-8356da50c42e627194d6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0002-9100000000-d73f7a96bae4c293dca5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4i-0900000000-bcfd295851c0251e17a5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03di-0900000000-647e329a4f1198a21c4eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-03di-0900000000-9712f63969dfeb7b2b12View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-03di-5900000000-20ecc3e0ff5e821384c2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-14i0-9900000000-808d3e185b47d908aa40View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0900000000-bcfd295851c0251e17a5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-647e329a4f1198a21c4eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-8460ae7eec787bc657b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-5900000000-20ecc3e0ff5e821384c2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-14i0-9900000000-808d3e185b47d908aa40View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-03di-0900000000-733155aa6e95d717f4b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0900000000-6593e0937f6ec62d47ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ku-9800000000-2ee8087a7bc4c5a7a1a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-e4e087704c73cc1a9643View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-ea9909ca4262eb8216a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07bp-2900000000-c9a1667de6cb3d4c547bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02im-9200000000-8aeb0201ddf350255af6View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Feces
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022197
KNApSAcK IDNot Available
Chemspider ID84994
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5679
PubChem Compound94180
PDB IDNot Available
ChEBI ID86543
References
Synthesis ReferenceSakaki, Keiji; Hara, Shigeki; Itoh, Naotsugu. Optical resolution of racemic 2-hydroxy octanoic acid using biphasic enzyme membrane reactor. Desalination (2002), 149(1-3), 247-252.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Jones JM, Morrell JC, Gould SJ: Identification and characterization of HAOX1, HAOX2, and HAOX3, three human peroxisomal 2-hydroxy acid oxidases. J Biol Chem. 2000 Apr 28;275(17):12590-7. [PubMed:10777549 ]
  2. Duran M, Wanders RJ, de Jager JP, Dorland L, Bruinvis L, Ketting D, Ijlst L, van Sprang FJ: 3-Hydroxydicarboxylic aciduria due to long-chain 3-hydroxyacyl-coenzyme A dehydrogenase deficiency associated with sudden neonatal death: protective effect of medium-chain triglyceride treatment. Eur J Pediatr. 1991 Jan;150(3):190-5. [PubMed:2044590 ]