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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2014-04-11 22:16:54 UTC
Update Date2021-09-14 15:45:32 UTC
HMDB IDHMDB0061652
Secondary Accession Numbers
  • HMDB61652
Metabolite Identification
Common Name3-Hydroxyhexanoic acid
Description(S)-3-hydroxyhexanoic acid 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-hydroxyhexanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1571930751
Synonyms
ValueSource
(S)-3-HydroxyhexanoateGenerator
(3S)-3-HydroxyhexanoateHMDB
(3S)-3-Hydroxyhexanoic acidHMDB
(S)-3-HydroxycaproateHMDB
(S)-3-Hydroxycaproic acidHMDB
(S)-3-Hydroxyhexanoic acidHMDB
(±)-3-HydroxyhexanoateHMDB
(±)-3-Hydroxyhexanoic acidHMDB
3-HydroxycaproateHMDB
3-Hydroxycaproic acidHMDB
3-HydroxyhexanoateHMDB
3-Hydroxyhexanoic acidHMDB
FA(6:0(3-OH))HMDB
FA(6:0(3S-OH))HMDB
beta-Hydroxy-n-caproateHMDB
beta-Hydroxy-n-caproic acidHMDB
beta-HydroxycaproateHMDB
beta-Hydroxycaproic acidHMDB
beta-HydroxyhexanoateHMDB
beta-Hydroxyhexanoic acidHMDB
β-Hydroxy-n-caproateHMDB
β-Hydroxy-n-caproic acidHMDB
β-HydroxycaproateHMDB
β-Hydroxycaproic acidHMDB
β-HydroxyhexanoateHMDB
β-Hydroxyhexanoic acidHMDB
Chemical FormulaC6H12O3
Average Molecular Weight132.159
Monoisotopic Molecular Weight132.078644246
IUPAC Name(3S)-3-hydroxyhexanoic acid
Traditional Name(S)-3-hydroxyhexanoic acid
CAS Registry Number66997-60-2
SMILES
CCC[C@H](O)CC(O)=O
InChI Identifier
InChI=1S/C6H12O3/c1-2-3-5(7)4-6(8)9/h5,7H,2-4H2,1H3,(H,8,9)/t5-/m0/s1
InChI KeyHPMGFDVTYHWBAG-YFKPBYRVSA-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

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility133 g/LALOGPS
logP10(0.57) g/LALOGPS
logP10(0.58) g/LChemAxon
logS10(0) g/LALOGPS
pKa (Strongest Acidic)4.67ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity32.59 m³·mol⁻¹ChemAxon
Polarizability13.87 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hydroxyhexanoic acid,1TMS,#1CCC[C@@H](CC(=O)O)O[Si](C)(C)C1221.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Hydroxyhexanoic acid,1TMS,#2CCC[C@H](O)CC(=O)O[Si](C)(C)C1196.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Hydroxyhexanoic acid,2TMS,#1CCC[C@@H](CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1311.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Hydroxyhexanoic acid,1TBDMS,#1CCC[C@@H](CC(=O)O)O[Si](C)(C)C(C)(C)C1445.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Hydroxyhexanoic acid,1TBDMS,#2CCC[C@H](O)CC(=O)O[Si](C)(C)C(C)(C)C1426.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Hydroxyhexanoic acid,2TBDMS,#1CCC[C@@H](CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1751.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxyhexanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyhexanoic acid 10V, Positive-QTOFsplash10-0avi-9100000000-82b86020a271d61ba1b52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyhexanoic acid 20V, Positive-QTOFsplash10-052f-9000000000-5b86d65468321ff154262021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyhexanoic acid 40V, Positive-QTOFsplash10-0006-9000000000-ab813e477e382c5c6c082021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyhexanoic acid 10V, Negative-QTOFsplash10-053r-6900000000-605bc451889b03fcac772021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyhexanoic acid 20V, Negative-QTOFsplash10-0a4l-9100000000-e58c13d9ebd5ab0dbbbf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxyhexanoic acid 40V, Negative-QTOFsplash10-0006-9000000000-191e4c2a7ad7ea5541dd2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified20 uMAdult (>18 years old)MaleNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified6-510 uMChildren (1-13 years old)Male3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Metastatic melanoma
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder 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 ]
Metastatic melanoma
  1. Frankel AE, Coughlin LA, Kim J, Froehlich TW, Xie Y, Frenkel EP, Koh AY: Metagenomic Shotgun Sequencing and Unbiased Metabolomic Profiling Identify Specific Human Gut Microbiota and Metabolites Associated with Immune Checkpoint Therapy Efficacy in Melanoma Patients. Neoplasia. 2017 Oct;19(10):848-855. doi: 10.1016/j.neo.2017.08.004. Epub 2017 Sep 15. [PubMed:28923537 ]
Associated OMIM IDs
  • 605911 (3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency)
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 Compound11829482
PDB IDNot Available
ChEBI ID37049
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. The AOCS Lipid Library [Link]