3-Hydroxyvaleric acid (CHEM003382)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 06:51:12 UTC
Update Date2026-04-16 20:55:34 UTC
Accession NumberCHEM003382
Identification
Common Name3-Hydroxyvaleric acid
ClassSmall Molecule
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. (1).
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • T3DB toxins
Contaminant Type
  • Animal Toxin
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Mass118.131 g/mol
Monoisotopic Mass118.063 g/mol
CAS Registry Number10237-77-1
IUPAC Name3-hydroxypentanoic acid
Traditional Nameβ-hydroxyvaleric acid
SMILESCCC(O)CC(O)=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Malonic AciduriaSMP00198 Not Available
Methylmalonic AciduriaSMP00200 Not Available
Methylmalonic Aciduria Due to Cobalamin-Related DisordersSMP00201 Not Available
Propionic AcidemiaSMP00236 Not Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056u-9000000000-fde9571755e6d3cddae3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dr-9510000000-9d8e25ae920466d4c511Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0gbc-9400000000-3dae3f739ba9de64475aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00di-9000000000-ec468e42a003a1f180bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-5900000000-a1bc76022730f161dafcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pc0-9400000000-bc4545952d0dabaa0a91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-e1433bba6aff8e1d8496Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-8900000000-454a4b12b6ccf58bb2bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-9200000000-3b62dff2b7068de77729Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-566ee0bbfee795fa4ab8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3900000000-435f90759fee859167e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9000000000-df01d36c99bd2c33adbbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-d49658fb47ced2654501Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9100000000-b0042e4aafbb3d04f7f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-25c5b53ebb683b2d03deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-5a37df2c9eb026290f1fSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000531
FooDB IDFDB022099
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5516
PDB IDNot Available
Wikipedia Link3-Hydroxypentanoic_acid
Chemspider ID96952
ChEBI ID139272
PubChem Compound ID107802
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceManufacture of b-hydroxyvaleric acid. Jpn. Kokai Tokkyo Koho (1982), 3 pp.
MSDSNot Available
General References
1. Manufacture of b-hydroxyvaleric acid. Jpn. Kokai Tokkyo Koho (1982), 3 pp.
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.
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.
4. 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.
5. 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.
6. Yuan L: [Propionic acidemia: one case report]. Zhongguo Yi Xue Ke Xue Yuan Xue Bao. 1991 Apr;13(2):141-3.