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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:17:17 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
Thumb
SynonymsNot Available
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
ClassificationNot classified
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Role

Indirect biological role:

Biological role:

Process

Naturally occurring process:

  Biological process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

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
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056u-9000000000-fde9571755e6d3cddae3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dr-9510000000-9d8e25ae920466d4c511View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-5900000000-a1bc76022730f161dafcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pc0-9400000000-bc4545952d0dabaa0a91View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-e1433bba6aff8e1d8496View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-8900000000-454a4b12b6ccf58bb2bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-9200000000-3b62dff2b7068de77729View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-566ee0bbfee795fa4ab8View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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 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
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified1 umol/mmol creatinineAdult (>18 years old)Not Specified
Propionic acidemia
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 IDFDB022099
KNApSAcK IDNot Available
Chemspider ID96952
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
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. [PubMed: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. [PubMed: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. [PubMed: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. [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 ]