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Human Metabolome Database Version 2.5

 

Showing metabocard for 2-Hydroxyadipic acid (HMDB00321)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2005-11-16 15:48:42
Update Date 2009-06-18 12:00:10
Accession Number HMDB00321
Secondary Accession Numbers Not Available
Common Name 2-Hydroxyadipic acid
Description 2-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)
Synonyms
  1. 2,3,4-Trideoxyhexarate
  2. 2,3,4-Trideoxyhexaric acid
  3. 2-Hydroxyadipate
  4. 2-Hydroxyadipic acid
  5. 2-Hydroxyhexanedioate
  6. 2-Hydroxyhexanedioic acid
  7. 2-hydroxy-adipate
  8. 2-hydroxy-adipic acid
  9. DL-2-Hydroxyadipate
  10. DL-2-Hydroxyadipic acid
  11. a-Hydroxyadipate
  12. a-Hydroxyadipic acid
  13. alpha-Hydroxyadipate
  14. alpha-Hydroxyadipic acid
  15. 2-hydroxy-hexanedioic acid
  16. 2-hydroxy-hexanedioate
Chemical IUPAC Name 2-hydroxyhexanedioic acid
Chemical Formula C6H10O5
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Dicarboxylic Acids
Sub Class
  • Short chain dicarboxylic acids
Family
  • Mammalian Metabolite
Species
  • secondary alcohol
  • carboxylic acid
  • alpha-hydroxyacid
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 162.141
Monoisotopic Molecular Weight 162.052826
Isomeric SMILES OC(CCCC(O)=O)C(O)=O
Canonical SMILES OC(CCCC(O)=O)C(O)=O
KEGG Compound ID C02360 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00321 Link Image
Metagene Link HMDB00321 Link Image
METLIN ID 5310 Link Image
PubChem Compound 193530 Link Image
PubChem Substance 14710848 Link Image
ChEBI ID 17023 Link Image
CAS Registry Number 18294-85-4
InChI Identifier InChI=1/C6H10O5/c7-4(6(10)11)2-1-3-5(8)9/h4,7H,1-3H2,(H,8,9)(H,10,11)
Synthesis Reference Griot, Rudolf. a-Hydroxyadipic acid. Helvetica Chimica Acta (1958), 41 2236-41.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 70.3 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -2
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -0.79 [Predicted by ALOGPS]; -0.8 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Varian)
Show Experimental Conditions Link Image
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
Show Experimental Conditions Link Image
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
Download File
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Medium Energy
Download File
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High Energy
Download File
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm (Predicted from LogP)
Biofluid Location
  • Urine
Tissue Location Not Available
Concentrations (Normal)
Biofluid Urine
Value 7.7 (0.1-19.6) umol/mmol creatinine
Age Newborn:0-30 days old
Sex Both
Patient information Normal
Comments Not Available
References
  • 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 Link Image]
Biofluid Urine
Value 7.3 (0.1-15.4) umol/mmol creatinine
Age Infant:0-1 yr old
Sex Both
Patient information Normal
Comments Not Available
References
  • 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 Link Image]
Biofluid Urine
Value 2.2 (0.1-6.8) umol/mmol creatinine
Age Children:1-13 yrs old
Sex Both
Patient information Normal
Comments Children aged 2-6 years
References
  • 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 Link Image]
Biofluid Urine
Value 1.6 (0.1-5.1) umol/mmol creatinine
Age Children:1-13 yrs old
Sex Both
Patient information Normal
Comments Children aged 6-10 years
References
  • 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 Link Image]
Biofluid Urine
Value 2.4 (0.1-5.8) umol/mmol creatinine
Age Adolescent:13-18 yrs old
Sex Both
Patient information Normal
Comments Children >10 years old
References
  • 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 Link Image]
Biofluid Urine
Value 1.0 (0.0-2.0) umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
Concentrations (Abnormal)
Biofluid Urine
Value 135.0 (50.0-220.0) umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Comments Not Available
References
Associated Disorders Not Available
OMIM ID Not Available
Pathways Not Available
General References
  1. 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 Link Image]
  2. 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 Link Image]
  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 Link Image]
  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 Link Image]