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Record Information
Version3.6
Creation Date2006-02-23 10:30:31 UTC
Update Date2017-08-16 03:48:02 UTC
HMDB IDHMDB0001863
Secondary Accession Numbers
  • HMDB01863
Metabolite Identification
Common Name2-Hydroxyvaleric acid
Description2-Hydroxyvaleric acid is an organic acid present in human biofluids. Its presence in urine has been associated with lactic acidosis, which occurs in Succinic Acidemia (OMIM 600335 ), a syndrome of organic acidemia associated with congenital lactic acidosis and decreased NADH-cytochrome c reductase activity. 2-Hydroxyvaleric acid presence associated with lactic acidosis has also been found in Propionyl-CoA carboxylase deficiency (OMIM 253260 ), or Multiple carboxylase deficiency (MCD), an autosomal recessive metabolic disorder characterized primarily by cutaneous and neurologic abnormalities. (PMID: 9389332 , 1790187 , 3378323 , 3383430 , 7313494 ).
Structure
Thumb
Synonyms
ValueSource
alpha-Hydroxy-N-valeric acidChEBI
alpha-Hydroxyvaleric acidChEBI
a-Hydroxy-N-valerateGenerator
a-Hydroxy-N-valeric acidGenerator
alpha-Hydroxy-N-valerateGenerator
α-hydroxy-N-valerateGenerator
α-hydroxy-N-valeric acidGenerator
2-HydroxyvalerateGenerator
a-HydroxyvalerateGenerator
a-Hydroxyvaleric acidGenerator
alpha-HydroxyvalerateGenerator
α-hydroxyvalerateGenerator
α-hydroxyvaleric acidGenerator
(+-)-2-HydroxypentanoateHMDB
(+-)-2-Hydroxypentanoic acidHMDB
(S)-2-Hydroxyvaleric acidHMDB
2-Hydroxy-pentanoateHMDB
2-Hydroxy-pentanoic acidHMDB
2-HydroxypentanoateHMDB
2-Hydroxypentanoic acidHMDB
DL-2-Hydroxy valeric acidHMDB
Chemical FormulaC5H10O3
Average Molecular Weight118.1311
Monoisotopic Molecular Weight118.062994186
IUPAC Name2-hydroxypentanoic acid
Traditional Namepentanoic acid, 2-hydroxy-
CAS Registry Number617-31-2
SMILES
CCCC(O)C(O)=O
InChI Identifier
InChI=1S/C5H10O3/c1-2-3-4(6)5(7)8/h4,6H,2-3H2,1H3,(H,7,8)
InChI KeyJRHWHSJDIILJAT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point34 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.45SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility204.0 mg/mLALOGPS
logP0.26ALOGPS
logP0.5ChemAxon
logS0.24ALOGPS
pKa (Strongest Acidic)4.14ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.96 m3·mol-1ChemAxon
Polarizability11.83 Å3ChemAxon
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-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-01b9-5900000000-01385a49616d72e0af48View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Infant (0-1 year old)Both
    Normal
    details
    UrineDetected and Quantified0.1 +/- 0.1 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Normal
    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 IDFDB022717
    KNApSAcK IDNot Available
    Chemspider ID88482
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB0001863
    METLIN IDNot Available
    PubChem Compound98009
    PDB IDNot Available
    ChEBI ID60647
    References
    Synthesis ReferenceD'yakonov, I. A.; Vinogradova, N. B. Reactions of aliphatic diazo compounds with unsaturated compounds. VIII. Reaction of diazoacetic ester with allyl bromide. Zhurnal Obshchei Khimii (1951), 21 851-60.
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Verhaeghe BJ, Lefevere MF, De Leenheer AP: Solid-phase extraction with strong anion-exchange columns for selective isolation and concentration of urinary organic acids. Clin Chem. 1988 Jun;34(6):1077-83. [PubMed:3378323 ]
    2. Bergstrom T, Greter J, Levin AH, Steen G, Tryding N, Wass U: Propionyl-CoA carboxylase deficiency: case report, effect of low-protein diet and identification of 3-oxo-2-methylvaleric acid 3-hydroxy-2-methylvaleric acid, and maleic acid in urine. Scand J Clin Lab Invest. 1981 Apr;41(2):117-26. [PubMed:7313494 ]
    3. Jellum E, Harboe M, Bjune G, Wold S: Interpreting complicated chromatographic patterns. J Pharm Biomed Anal. 1991;9(8):663-9. [PubMed:1790187 ]
    4. Kim KR, Kim JH, Jeong DH, Paek DJ, Liebich HM: Gas chromatographic profiling analysis of urinary organic acids from nonsmokers and smokers. J Chromatogr B Biomed Sci Appl. 1997 Nov 7;701(1):1-8. [PubMed:9389332 ]
    5. Asano K, Miyamoto I, Matsushita T, Murakami Y, Minoura S, Wagatsuma T, Oshima M: Succinic acidemia: a new syndrome of organic acidemia associated with congenital lactic acidosis and decreased NADH-cytochrome c reductase activity. Clin Chim Acta. 1988 Apr 29;173(3):305-12. [PubMed:3383430 ]