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Human Metabolome Database Version 2.5

 

Showing metabocard for Adipic acid (HMDB00448)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2005-11-16 15:48:42
Update Date 2009-08-11 15:12:14
Accession Number HMDB00448
Secondary Accession Numbers HMDB04862
Common Name Adipic acid
Description Adipic acid is a compound of the class of carboxylic acids that is derived from oxidation of various fats. It is a white crystalline powder appearing as an acid in aqueous circumstances, though it is not highly soluble (wikipedia)
Synonyms
  1. 1,6-Hexanedioate
  2. 1,6-Hexanedioic acid
  3. Acifloctin
  4. Acinetten
  5. Adi-pure
  6. Adilactetten
  7. Adipate
  8. Adipic acid
  9. Adipinate
  10. Adipinic acid
  11. Hexanedioate
  12. Hexanedioic acid
  13. Kyselina adipova
  14. Molten adipate
  15. Molten adipic acid
Chemical IUPAC Name hexanedioic acid
Chemical Formula C6H10O4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Dicarboxylic Acids
Sub Class
  • Short chain dicarboxylic acids
Family
  • Mammalian Metabolite
Species
  • carboxylic acid
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 146.141
Monoisotopic Molecular Weight 146.057907
Isomeric SMILES OC(=O)CCCCC(O)=O
Canonical SMILES OC(=O)CCCCC(O)=O
KEGG Compound ID C06104 Link Image
BioCyc ID CPD-468 Link Image
BiGG ID Not Available
Wikipedia Link Adipic acid Link Image
NuGOwiki Link HMDB00448 Link Image
Metagene Link HMDB00448 Link Image
METLIN ID 115 Link Image
PubChem Compound 196 Link Image
PubChem Substance 11528289 Link Image
ChEBI ID 30832 Link Image
CAS Registry Number 124-04-9
InChI Identifier InChI=1/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10)
Synthesis Reference Saito, Kenji. Recovery of adipic acid. Jpn. Kokai Tokkyo Koho (1976), 5 pp.
Melting Point (Experimental) 151-154 oC
Experimental Water Solubility 30.8 mg/mL at 34 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] Source: PhysProp
Predicted Water Solubility 32.2 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -2
State Liquid
Experimental LogP/Hydrophobicity 0.08 [HANSCH,C ET AL. (1995)] Source: PhysProp
Predicted LogP/Hydrophobicity 0.13 [Predicted by ALOGPS]; 0 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
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 Download Spectrum
Download FID (Bruker)
Show Experimental Conditions Link Image
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
Show Peaklist
Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
Show Experimental Conditions Link Image
High Energy
Download File
Show Experimental Conditions Link Image
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
Biofluid Location
  • Blood
  • Cerebrospinal Fluid
  • Urine
Tissue Location Not Available
Concentrations (Normal)
Biofluid Blood
Value 0.09 +/- 0.010 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.
Biofluid CSF
Value 0.32 - 2.16 uM
Age Children:1-13 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Suh JW, Lee SH, Chung BC: GC-MS determination of organic acids with solvent extraction after cation-exchange chromatography. Clin Chem. 1997 Dec;43(12):2256-61. [PubMed Link Image]
Biofluid Urine
Value 9.2 (0.1-19.9) 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 11.4 (0.1-14.8) 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 4.0 (1.9-9.6) umol/mmol creatinine
Age Children:1-13 yrs 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 2.4 (1.2-7.0) umol/mmol creatinine
Age Adolescent:13-18 yrs 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 8.4 +/- 5.3 umol/mmol creatinine
Age Adolescent:13-18 yrs old
Sex Female
Patient information Normal
Comments Not Available
References
  • Capo-chichi CD, Gueant JL, Lefebvre E, Bennani N, Lorentz E, Vidailhet C, Vidailhet M: Riboflavin and riboflavin-derived cofactors in adolescent girls with anorexia nervosa. Am J Clin Nutr. 1999 Apr;69(4):672-8. [PubMed Link Image]
Biofluid Urine
Value 2.87 +/- 2.50 umol/mmol creatinine
Age Infant:0-1 yr old
Sex Both
Patient information Normal
Comments Not Available
References
  • Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed Link Image]
Biofluid Urine
Value 6.0 (2.0-11.0) umol/mmol creatinine
Age Infant:0-1 yr old
Sex Both
Patient information Normal
Comments Not Available
References
  • Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Biofluid Urine
Value 39 +/- 1 uM
Age Adult:>18 yrs old
Sex Male
Patient information Normal
Comments Not Available
References
  • Shaykhutdinov RA, MacInnis GD, Dowlatabadi R, Weljie AM, Vogel HJ. Quantitative analysis of metabolite concentrations in human urine samples using 13C{1H} NMR spectroscopy. Metabolomics. 2009
Biofluid Urine
Value 17.15 (0.00-34.30) umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
Biofluid Urine
Value 130.00 +/- 60.00 umol/mmol creatinine
Age Children:1-13 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Capo-Chichi CD, Feillet F, Gueant JL, Amouzou K, Zonon N, Sanni A, Lefebvre E, Assimadi K, Vidailhet M: Concentrations of riboflavin and related organic acids in children with protein-energy malnutrition. Am J Clin Nutr. 2000 Apr;71(4):978-86. [PubMed Link Image]
Biofluid Urine
Value 13.00 +/- 5.4 umol/mmol creatinine
Age Children:1-13 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Abnormal urinary excretion of unsaturated dicarboxylic acids in patients with medium-chain acyl-CoA dehydrogenase deficiency. J Lipid Res. 1990 May;31(5):763-71. [PubMed Link Image]
Concentrations (Abnormal)
Biofluid Urine
Value 2.0 (0.0-28.0) umol/mmol creatinine
Age N/A
Sex Both
Condition Lung Cancer
Comments Not Available
References
  • HMP experimental
Biofluid Urine
Value 8.6 +/- 8.3 umol/mmol creatinine
Age Adolescent:13-18 yrs old
Sex Female
Condition Anorexia nervosa
Comments Not Available
References
  • Capo-chichi CD, Gueant JL, Lefebvre E, Bennani N, Lorentz E, Vidailhet C, Vidailhet M: Riboflavin and riboflavin-derived cofactors in adolescent girls with anorexia nervosa. Am J Clin Nutr. 1999 Apr;69(4):672-8. [PubMed Link Image]
Biofluid Urine
Value 31.0 (12.0-50.0) umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Condition 3-Hydroxy-3-methylglutaryl-CoA lyase deficiency
Comments Not Available
References
Biofluid Urine
Value 800.00 (0.00-1600.00) umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Condition Glutaric acidemia type 2
Comments Not Available
References
Biofluid Urine
Value 26.35 +/- 13.6 umol/mmol creatinine
Age Children:1-13 yrs old
Sex Both
Comments Not Available
References
  • Capo-Chichi CD, Feillet F, Gueant JL, Amouzou K, Zonon N, Sanni A, Lefebvre E, Assimadi K, Vidailhet M: Concentrations of riboflavin and related organic acids in children with protein-energy malnutrition. Am J Clin Nutr. 2000 Apr;71(4):978-86. [PubMed Link Image]
Associated Disorders
Condition References
3-Hydroxy-3-methylglutaryl-CoA lyase deficiency
Anorexia nervosa
  • Capo-chichi CD, Gueant JL, Lefebvre E, Bennani N, Lorentz E, Vidailhet C, Vidailhet M: Riboflavin and riboflavin-derived cofactors in adolescent girls with anorexia nervosa. Am J Clin Nutr. 1999 Apr;69(4):672-8. [PubMed Link Image]
Glutaric acidemia type 2
Lung Cancer
  • HMP experimental
OMIM ID
Pathways Not Available
General References
  1. Coude MM, Charpentier C, Bonnefont JP, Cheron G, Kamoun P: Organic acids in aqueous humour and plasma: post mortem study in infants and diagnosis of enzymopathies. J Inherit Metab Dis. 1991;14(5):668-73. [PubMed Link Image]
  2. Pettersen JE: In vivo studies on the metabolism of hexanedioic acid. Clin Chim Acta. 1975 Jan 6;58(1):43-50. [PubMed Link Image]
  3. Matsumoto M, Kuhara T, Inoue Y, Shinka T, Matsumoto I: Abnormal fatty acid metabolism in patients in hopantenate therapy during clinical episodes. J Chromatogr. 1991 Jan 2;562(1-2):139-45. [PubMed Link Image]
  4. Jakobs C, Sweetman L, Wadman SK, Duran M, Saudubray JM, Nyhan WL: Prenatal diagnosis of glutaric aciduria type II by direct chemical analysis of dicarboxylic acids in amniotic fluid. Eur J Pediatr. 1984 Jan;141(3):153-7. [PubMed Link Image]
  5. Greter J, Lindstedt S, Steen G: Urinary metabolites of cis-9,10-methylene octadecanoic acid. cis-3,4-Methylene hexanedioic acid and related compounds. J Biol Chem. 1979 Apr 25;254(8):2807-13. [PubMed Link Image]
  6. Wikipedia Link Image