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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:29 UTC
Update Date2019-10-24 17:02:47 UTC
HMDB IDHMDB0001954
Secondary Accession Numbers
  • HMDB01954
Metabolite Identification
Common Name3-Hydroxyoctanoic acid
Description(S)-3-hydroxyoctanoic acid, also known as (S)-3-OH-caprylic acid or (S)-3-hydroxycaprylate, belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain (S)-3-hydroxyoctanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1571936567
Synonyms
ValueSource
(3S)-3-Hydroxy-octanoic acidChEBI
(S)-3-Hydroxycaprylic acidChEBI
(S)-3-OH Octanoic acidChEBI
(S)-3-OH-Caprylic acidChEBI
(S)-beta-Hydroxycaprylic acidChEBI
(S)-beta-Hydroxyoctanoic acidChEBI
(S)-beta-OH-Caprylic acidChEBI
(S)-beta-OH-Octanoic acidChEBI
(3S)-3-Hydroxy-octanoateGenerator
(S)-3-HydroxycaprylateGenerator
(S)-3-OH OctanoateGenerator
(S)-3-OH-CaprylateGenerator
(S)-b-HydroxycaprylateGenerator
(S)-b-Hydroxycaprylic acidGenerator
(S)-beta-HydroxycaprylateGenerator
(S)-Β-hydroxycaprylateGenerator
(S)-Β-hydroxycaprylic acidGenerator
(S)-b-HydroxyoctanoateGenerator
(S)-b-Hydroxyoctanoic acidGenerator
(S)-beta-HydroxyoctanoateGenerator
(S)-Β-hydroxyoctanoateGenerator
(S)-Β-hydroxyoctanoic acidGenerator
(S)-b-OH-CaprylateGenerator
(S)-b-OH-Caprylic acidGenerator
(S)-beta-OH-CaprylateGenerator
(S)-Β-OH-caprylateGenerator
(S)-Β-OH-caprylic acidGenerator
(S)-b-OH-OctanoateGenerator
(S)-b-OH-Octanoic acidGenerator
(S)-beta-OH-OctanoateGenerator
(S)-Β-OH-octanoateGenerator
(S)-Β-OH-octanoic acidGenerator
(S)-3-HydroxyoctanoateGenerator
3-Hydroxyoctanoic acidMeSH
3-HydroxyoctanoateMeSH
3-Hydroxyoctanoic acid, (S)-isomerMeSH
(3S)-3-HydroxyoctanoateHMDB
(3S)-3-Hydroxyoctanoic acidHMDB
(±)-3-HydroxyoctanoateHMDB
(±)-3-Hydroxyoctanoic acidHMDB
3-HydroxycaprylateHMDB
3-Hydroxycaprylic acidHMDB
FA(8:0(3-OH))HMDB
FA(8:0(3S-OH))HMDB
S-3-HydroxyoctanoateHMDB
S-3-Hydroxyoctanoic acidHMDB
beta-HydroxycaprylateHMDB
beta-Hydroxycaprylic acidHMDB
beta-HydroxyoctanoateHMDB
beta-Hydroxyoctanoic acidHMDB
β-HydroxycaprylateHMDB
β-Hydroxycaprylic acidHMDB
β-HydroxyoctanoateHMDB
β-Hydroxyoctanoic acidHMDB
Chemical FormulaC8H16O3
Average Molecular Weight160.2108
Monoisotopic Molecular Weight160.109944378
IUPAC Name(3S)-3-hydroxyoctanoic acid
Traditional Name(S)-3-hydroxyoctanoic acid
CAS Registry Number33796-86-0
SMILES
CCCCC[C@H](O)CC(O)=O
InChI Identifier
InChI=1S/C8H16O3/c1-2-3-4-5-7(9)6-8(10)11/h7,9H,2-6H2,1H3,(H,10,11)/t7-/m0/s1
InChI KeyNDPLAKGOSZHTPH-ZETCQYMHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassMedium-chain hydroxy acids and derivatives
Direct ParentMedium-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Hydroxy fatty acid
  • Fatty acyl
  • Fatty acid
  • 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

Source:

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 Solubility13.6 g/LALOGPS
logP1.44ALOGPS
logP1.47ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)4.84ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity41.79 m³·mol⁻¹ChemAxon
Polarizability17.97 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00ov-5920000000-2c7ce12b4e2e186a597fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00ov-5920000000-2c7ce12b4e2e186a597fJSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.65(0.32-1.2) uMInfant (0-1 year old)Not SpecifiedNormal details
BloodDetected and Quantified20 uMAdult (>18 years old)MaleNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.95-33.5 uMInfant (0-1 year old)Female3-Hydroxydicarboxylic aciduria details
BloodDetected and Quantified3-2400 uMChildren (1-13 years old)Male3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency
  1. Thompson GN, Hsu BY, Pitt JJ, Treacy E, Stanley CA: Fasting hypoketotic coma in a child with deficiency of mitochondrial 3-hydroxy-3-methylglutaryl-CoA synthase. N Engl J Med. 1997 Oct 23;337(17):1203-7. doi: 10.1056/NEJM199710233371704. [PubMed:9337379 ]
3-Hydroxydicarboxylic aciduria
  1. Hagenfeldt L, von Dobeln U, Holme E, Alm J, Brandberg G, Enocksson E, Lindeberg L: 3-Hydroxydicarboxylic aciduria--a fatty acid oxidation defect with severe prognosis. J Pediatr. 1990 Mar;116(3):387-92. [PubMed:2308028 ]
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 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
  • 605911 (3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency)
  • 114500 (Colorectal cancer)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022761
KNApSAcK IDNot Available
Chemspider ID9542083
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-Hydroxyoctanoic acid
METLIN IDNot Available
PubChem Compound11367166
PDB IDNot Available
ChEBI ID37100
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceTahara, Satoshi; Suzuki, Yumiko; Mizutani, Junya. Fungal metabolism of a,b-unsaturated carboxylic acids. Part III. Fungal metabolism of trans-2-octenoic acid. Agricultural and Biological Chemistry (1977), 41(9), 1643-50.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Urinary 3-hydroxydicarboxylic acids in pathophysiology of metabolic disorders with dicarboxylic aciduria. Metabolism. 1991 Jul;40(7):676-82. [PubMed:1870421 ]
  2. Jones PM, Butt Y, Bennett MJ: Accumulation of 3-hydroxy-fatty acids in the culture medium of long-chain L-3-hydroxyacyl CoA dehydrogenase (LCHAD) and mitochondrial trifunctional protein-deficient skin fibroblasts: implications for medium chain triglyceride dietary treatment of LCHAD deficiency. Pediatr Res. 2003 May;53(5):783-7. Epub 2003 Mar 5. [PubMed:12621125 ]
  3. Montgomery JA, Mamer OA, Colle E: Profiles in altered metabolism. IV--Induction of acute dicarboxylic aciduria following 2-octynoic acid administration to the rat. Biomed Environ Mass Spectrom. 1989 Jun;18(6):416-23. [PubMed:2765701 ]
  4. Kelley RI, Morton DH: 3-Hydroxyoctanoic aciduria: identification of a new organic acid in the urine of a patient with non-ketotic hypoglycemia. Clin Chim Acta. 1988 Jun 30;175(1):19-26. [PubMed:3168281 ]
  5. Bennett MJ, Ragni MC, Hood I, Hale DE: Comparison of post-mortem urinary and vitreous humour organic acids. Ann Clin Biochem. 1992 Sep;29 ( Pt 5):541-5. [PubMed:1444166 ]