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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:25:36 UTC
HMDB IDHMDB00321
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Hydroxyadipic acid
Description2-Hydroxyadipic acid is a hydroxy-dicarboxylic acid formed by the reduction of 2-ketoadipic acid. Deficiency of 2-ketoadipic dehydrogenase causes 2-ketoadipic acidemia (OMIM 245130 ), a condition characterized by accumulation and excretion of 2-hydroxyadipic acid (with 2-ketoadipic and 2-aminoadipic) probably without adverse phenotypic effects.(OMMBID - The Metabolic and Molecular Bases of Inherited Disease, CH.95). A method involving derivatization and combined gas chromatography--mass spectrometry has been recently developed to separate the enantiomers of 3-hydroxyadipic acid (PMID: 3980660 ). It has been shown that 3-hydroxyadipic acid excreted in urine consists of at least 95% of the L-enantiomer. This finding supports the hypothesis that dicarboxylic acids are degraded by ordinary beta-oxidation, and indicates that adipic acid may be converted into succinic acid. (PMID: 3980660 ).
Structure
Thumb
Synonyms
  1. 2,3,4-Trideoxyhexarate
  2. 2,3,4-Trideoxyhexaric acid
  3. 2-Hydroxy-adipate
  4. 2-Hydroxy-adipic acid
  5. 2-Hydroxy-hexanedioate
  6. 2-Hydroxy-hexanedioic acid
  7. 2-Hydroxyadipate
  8. 2-Hydroxyadipic acid
  9. 2-Hydroxyhexanedioate
  10. 2-Hydroxyhexanedioic acid
  11. a-Hydroxyadipate
  12. a-Hydroxyadipic acid
  13. alpha-Hydroxyadipate
  14. alpha-Hydroxyadipic acid
  15. DL-2-Hydroxyadipate
  16. DL-2-Hydroxyadipic acid
Chemical FormulaC6H10O5
Average Molecular Weight162.1406
Monoisotopic Molecular Weight162.05282343
IUPAC Name2-hydroxyhexanedioic acid
Traditional Name2-hydroxyadipic acid
CAS Registry Number18294-85-4
SMILES
OC(CCCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H10O5/c7-4(6(10)11)2-1-3-5(8)9/h4,7H,1-3H2,(H,8,9)(H,10,11)
InChI KeyOTTXIFWBPRRYOG-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassOrganic Acids and Derivatives
ClassHydroxy Acids and Derivatives
Sub ClassMedium-chain Hydroxy Acids and Derivatives
Other Descriptors
  • 2-hydroxydicarboxylic acid(ChEBI)
  • Aliphatic Acyclic Compounds
  • Dicarboxylic acids(Lipidmaps)
  • Fatty Acids and Conjugates
Substituents
  • Alpha Hydroxy Acid
  • Carboxylic Acid
  • Dicarboxylic Acid Derivative
  • Secondary Alcohol
Direct ParentMedium-chain Hydroxy Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 Solubility70.3ALOGPS
logP-0.79ALOGPS
logP-0.38ChemAxon
logS-0.36ALOGPS
pKa (Strongest Acidic)3.44ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity34.23 m3·mol-1ChemAxon
Polarizability14.88 Å3ChemAxon
Spectra
SpectraGC-MSMS/MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
UrineDetected and Quantified7.7 (0.1-19.6) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified7.3 (0.1-15.4) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified2.2 (0.1-6.8) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified1.6 (0.1-5.1) umol/mmol creatinineChildren (1-13 years old)Both
Normal
details
UrineDetected and Quantified2.4 (0.1-5.8) umol/mmol creatinineAdolescent (13-18 years old)Both
Normal
details
UrineDetected and Quantified1.0 (0.0-2.0) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified135.0 (50.0-220.0) umol/mmol creatinineChildren (1-13 years old)Both2-Ketoadipic Acidemia details
Associated Disorders and Diseases
Disease References
2-ketoadipic acidemia
  1. MetaGene
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021947
KNApSAcK IDNot Available
Chemspider ID167943
KEGG Compound IDC02360
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00321
Metagene LinkHMDB00321
METLIN ID5310
PubChem Compound193530
PDB IDNot Available
ChEBI ID17023
References
Synthesis ReferenceGriot, Rudolf. a-Hydroxyadipic acid. Helvetica Chimica Acta (1958), 41 2236-41.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. Pubmed: 8087979
  2. Sewell AC, Heil M, Podebrad F, Mosandl A: Chiral compounds in metabolism: a look in the molecular mirror. Eur J Pediatr. 1998 Mar;157(3):185-91. Pubmed: 9537483
  3. Inoue Y, Shinka T, Ohse M, Kuhara T: Differential chemical diagnosis of primary hyperoxaluria type II. Highly sensitive analysis of optical isomers of glyceric acid by GC/MS as diastereoisomeric derivatives. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 25;823(1):2-6. Epub 2005 Apr 25. Pubmed: 16055048
  4. Svendsen JS, Whist JE, Sydnes LK: Absolute configuration of 3-hydroxyadipic acid in human urine. J Chromatogr. 1985 Jan 11;337(1):9-19. Pubmed: 3980660