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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:15 UTC
HMDB IDHMDB0000531
Secondary Accession Numbers
  • HMDB00531
Metabolite Identification
Common Name3-Hydroxyvaleric acid
Description3-Hydroxyvaleric acid may be products of the condensation of propionyl-CoA with acetyl-CoA catalyzed by 3-oxoacyl-CoA thiolases. An increase amount of 3-hydroxyvaleric acid can be found in methylmalonic acidemia and propionic acidemia. (PMID: 630060 ).
Structure
Data?1563860655
Synonyms
ValueSource
3-Hydroxy valeric acidChEBI
3-Hydroxy-pentanoic acidChEBI
3-Hydroxy-valeric acidChEBI
beta-Hydroxypentanoic acidChEBI
beta-Hydroxyvaleric acidChEBI
3-Hydroxy valerateGenerator
3-Hydroxy-pentanoateGenerator
3-Hydroxy-valerateGenerator
b-HydroxypentanoateGenerator
b-Hydroxypentanoic acidGenerator
beta-HydroxypentanoateGenerator
Β-hydroxypentanoateGenerator
Β-hydroxypentanoic acidGenerator
b-HydroxyvalerateGenerator
b-Hydroxyvaleric acidGenerator
beta-HydroxyvalerateGenerator
Β-hydroxyvalerateGenerator
Β-hydroxyvaleric acidGenerator
3-HydroxyvalerateGenerator
3-Hydroxy-N-valerateHMDB
3-Hydroxy-N-valeric acidHMDB
3-HydroxypentanoateHMDB
3-Hydroxypentanoic acidHMDB
b-Hydroxy-N-valerateHMDB
b-Hydroxy-N-valeric acidHMDB
beta-Hydroxy-N-valerateHMDB
beta-Hydroxy-N-valeric acidHMDB
3-Hydroxyvaleric acidChEBI
Chemical FormulaC5H10O3
Average Molecular Weight118.1311
Monoisotopic Molecular Weight118.062994186
IUPAC Name3-hydroxypentanoic acid
Traditional Nameβ-hydroxyvaleric acid
CAS Registry Number10237-77-1
SMILES
CCC(O)CC(O)=O
InChI Identifier
InChI=1S/C5H10O3/c1-2-4(6)3-5(7)8/h4,6H,2-3H2,1H3,(H,7,8)
InChI KeyREKYPYSUBKSCAT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Branched fatty acid
  • Hydroxy fatty acid
  • Short-chain hydroxy acid
  • Methyl-branched fatty acid
  • Hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen 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
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility371 g/LALOGPS
logP0.04ALOGPS
logP0.14ChemAxon
logS0.5ALOGPS
pKa (Strongest Acidic)4.56ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.99 m³·mol⁻¹ChemAxon
Polarizability11.95 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056u-9000000000-fde9571755e6d3cddae3JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dr-9510000000-9d8e25ae920466d4c511JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-5900000000-a1bc76022730f161dafcJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pc0-9400000000-bc4545952d0dabaa0a91JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-e1433bba6aff8e1d8496JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-8900000000-454a4b12b6ccf58bb2bfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-9200000000-3b62dff2b7068de77729JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-566ee0bbfee795fa4ab8JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.0 (0.0-2.0) uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified1 (0-2) uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not Quantified Infant (0-1 year old)Both
Normal
details
UrineDetected and Quantified0.87-1.4 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified<20 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1 (0-2) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.94-1.2 umol/mmol creatinineAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified1 umol/mmol creatinineAdult (>18 years old)Not Specified
Propionic acidemia
details
Associated Disorders and Diseases
Disease References
Propionic acidemia
  1. Riemersma M, Hazebroek MR, Helderman-van den Enden ATJM, Salomons GS, Ferdinandusse S, Brouwers MCGJ, van der Ploeg L, Heymans S, Glatz JFC, van den Wijngaard A, Krapels IPC, Bierau J, Brunner HG: Propionic acidemia as a cause of adult-onset dilated cardiomyopathy. Eur J Hum Genet. 2017 Nov;25(11):1195-1201. doi: 10.1038/ejhg.2017.127. Epub 2017 Aug 30. [PubMed:28853722 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022099
KNApSAcK IDNot Available
Chemspider ID96952
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-Hydroxypentanoic_acid
METLIN ID5516
PubChem Compound107802
PDB IDNot Available
ChEBI ID139272
References
Synthesis ReferenceManufacture of b-hydroxyvaleric acid. Jpn. Kokai Tokkyo Koho (1982), 3 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sweetman L, Weyler W, Nyhan WL, de Cespedes C, Loria AR, Estrada Y: Abnormal metabolites of isoleucine in a patient with propionyl-CoA carboxylase deficiency. Biomed Mass Spectrom. 1978 Mar;5(3):198-207. [PubMed:630060 ]
  2. Kuhara T, Inoue Y, Shinka T, Matsumoto I, Matsuo M: Identification of 3-hydroxy-3-ethylglutaric acid in urine of patients with propionic acidaemia. Biomed Mass Spectrom. 1983 Dec;10(12):629-32. [PubMed:6200156 ]
  3. Kuhara T, Matsumoto I: Studies on the urinary acidic metabolites from three patients with methylmalonic aciduria. Biomed Mass Spectrom. 1980 Oct;7(10):424-8. [PubMed:6111361 ]
  4. Boger J, Payne LS, Perlow DS, Lohr NS, Poe M, Blaine EH, Ulm EH, Schorn TW, LaMont BI, Lin TY, et al.: Renin inhibitors. Syntheses of subnanomolar, competitive, transition-state analogue inhibitors containing a novel analogue of statine. J Med Chem. 1985 Dec;28(12):1779-90. [PubMed:3906131 ]
  5. Yuan L: [Propionic acidemia: one case report]. Zhongguo Yi Xue Ke Xue Yuan Xue Bao. 1991 Apr;13(2):141-3. [PubMed:1831712 ]