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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:48 UTC
HMDB IDHMDB00531
Secondary Accession NumbersNone
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
Thumb
Synonyms
ValueSource
3-Hydroxy-N-valerateHMDB
3-Hydroxy-N-valeric acidHMDB
3-Hydroxy-valerateHMDB
3-Hydroxy-valeric acidHMDB
3-HydroxypentanoateHMDB
3-Hydroxypentanoic acidHMDB
3-HydroxyvalerateHMDB
b-Hydroxy-N-valerateHMDB
b-Hydroxy-N-valeric acidHMDB
b-HydroxyvalerateHMDB
b-Hydroxyvaleric acidHMDB
beta-Hydroxy-N-valerateHMDB
beta-Hydroxy-N-valeric acidHMDB
beta-HydroxyvalerateHMDB
beta-Hydroxyvaleric acidHMDB
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 KeyInChIKey=REKYPYSUBKSCAT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Short-chain hydroxy acid
  • Branched fatty acid
  • Beta-hydroxy acid
  • Hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 Solubility371.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.99 m3·mol-1ChemAxon
Polarizability11.95 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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 QuantifiedNot ApplicableInfant (0-1 year old)Both
Normal
details
UrineDetected and Quantified1 (0-2) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
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 IDFDB022099
KNApSAcK IDNot Available
Chemspider ID96952
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00531
Metagene LinkHMDB00531
METLIN ID5516
PubChem Compound107802
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceManufacture of b-hydroxyvaleric acid. Jpn. Kokai Tokkyo Koho (1982), 3 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [6111361 ]
  2. 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. [630060 ]
  3. 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. [6200156 ]
  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. [3906131 ]
  5. Yuan L: [Propionic acidemia: one case report] Zhongguo Yi Xue Ke Xue Yuan Xue Bao. 1991 Apr;13(2):141-3. [1831712 ]