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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-06-10 21:22:22 UTC
HMDB IDHMDB00448
Secondary Accession Numbers
  • HMDB04862
Metabolite Identification
Common NameAdipic acid
DescriptionAdipic acid is an important inudstrial dicarboxylic acid with about 2.5 billion kilograms produced per year. It is used mainly in the production of nylon. It occurs relatively rarely in nature. It has a tart taste and is also used as an additive and gelling agent in jello or gelatins. It is also used in some calcium carbonate antacids to make them tart. Adipic acid has also been incorporated into controlled-release formulation matrix tablets to obtain pH-independent release for both weakly basic and weakly acidic drugs. Adipic acid in the urine and in the blood is typically exogenous in origin and is a good biomarker of jello consumption. In fact, a condition known as adipic aciduria is actually an artifact of jello consumption (PMID: 1779643 ). However, certain disorders (such as diabetes and glutaric aciduria type I.) can lead to elevated levels of adipic acid snd other dicarboxcylic acids (such as suberic acid) in urine (PMID: 17520433 ; PMID: 6778884 ).
Structure
Thumb
Synonyms
ValueSource
1,4-Butanedicarboxylic acidChEBI
1,6-Hexanedioic acidChEBI
Adipinic acidChEBI
AdipinsaeureChEBI
e 355ChEBI
e-355ChEBI
e355ChEBI
INS no. 355ChEBI
1,4-ButanedicarboxylateGenerator
AdipateGenerator
1,6-HexanedioateGenerator
AdipinateGenerator
AcifloctinHMDB
AcinettenHMDB
Adi-pureHMDB
AdilactettenHMDB
HexanedioateHMDB
Hexanedioic acidHMDB
Kyselina adipovaHMDB
Molten adipateHMDB
Molten adipic acidHMDB
Chemical FormulaC6H10O4
Average Molecular Weight146.1412
Monoisotopic Molecular Weight146.057908808
IUPAC Namehexanedioic acid
Traditional Nameadipic acid
CAS Registry Number124-04-9
SMILES
OC(=O)CCCCC(O)=O
InChI Identifier
InChI=1S/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10)
InChI KeyInChIKey=WNLRTRBMVRJNCN-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug
  • Drug metabolite
  • Food
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point151 - 154 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility30.8 mg/mL at 34 °CNot Available
LogP0.08HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility32.2 mg/mLALOGPS
logP0.13ALOGPS
logP0.49ChemAxon
logS-0.66ALOGPS
pKa (Strongest Acidic)3.92ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity32.74 m3·mol-1ChemAxon
Polarizability14.24 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-03dj-0900000000-5378ec232b7bc8c84368View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-03di-2920000000-a4bb0f67851a49bcd19cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000x-3900000000-1c5a6a5287f8fd7736f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-001i-9100000000-3e9496a6da881edd91e0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0uea-9500000000-edb5529010e4b88414c4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-0a6u-9000000000-36d8bc2f7d1a77a7b466View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-a1852cfc66b4feae9b18View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0ue9-6900000000-90e783cc3522f0ce7880View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-9200000000-b5a64d560d8bc62d8d51View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001i-9000000000-a96d5ee9551b944e4db8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001i-9000000000-2e61b7d2a4dbc9867123View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0f6x-9200000000-988f76bb42297a8d9d3bView in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.09 +/- 0.010 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.32 - 2.16 uMChildren (1-13 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected and Quantified147.118 +/- 90.324 uMNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
SalivaDetected and Quantified0.0658 +/- 0.107 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.0813 +/- 0.111 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.124 +/- 0.115 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.171 +/- 0.159 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected and Quantified9.2 (0.1-19.9) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified11.4 (0.1-14.8) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified4.0 (1.9-9.6) umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified2.4 (1.2-7.0) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected and Quantified8.4 +/- 5.3 umol/mmol creatinineAdolescent (13-18 years old)FemaleNormal details
UrineDetected and Quantified2.87 +/- 2.50 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified0.84-1.9 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified130.00 +/- 60.00 umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified13.00 +/- 5.4 umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified6.0 (2.0-11.0) umol/mmol creatinineInfant (0-1 year old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified2.82 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Shaykhutdinov RA,...
details
UrineDetected and Quantified5.1 (0.8-35) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified<28.79 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
details
UrineDetected and Quantified0.4 +/- 0.6 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.72-1.2 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified4.4 (1.6-14.3) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.2 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified3.0 (1.0-12.9) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified4.47 +/- 5.757 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified8.6 +/- 8.3 umol/mmol creatinineAdolescent (13-18 years old)FemaleAnorexia nervosa details
UrineDetected and Quantified26.35 +/- 13.6 umol/mmol creatinineChildren (1-13 years old)BothMalnutrition (type kwashiorkor and marasmus) details
UrineDetected and Quantified2.0 (0.0-28.0) umol/mmol creatinineNot SpecifiedBothLung cancer details
UrineDetected and Quantified8.582 +/- 7.258 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified800.00 (0.00-1600.00) umol/mmol creatinineChildren (1-13 years old)BothGlutaric Aciduria II details
UrineDetected and Quantified17.15 (0.00-34.30) umol/mmol creatinineAdult (>18 years old)Both3-Hydroxy-3-methylglutaryl-CoA lyase deficiency details
UrineDetected and Quantified31.0 (12.0-50.0) umol/mmol creatinineChildren (1-13 years old)Both3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency details
UrineDetected and Quantified9.173 +/- 20.147 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified31.806 +/- 75.777 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
3-Hydroxy-3-methylglutaryl-CoA lyase deficiency
  1. MetaGene [Link]
Anorexia nervosa
  1. 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. [10197568 ]
Glutaric acidemia type 2
  1. MetaGene [Link]
Lung Cancer
  1. Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2008 Oct 25. [18953024 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00501
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008309
KNApSAcK IDC00001178
Chemspider ID191
KEGG Compound IDC06104
BioCyc IDADIPATE
BiGG IDNot Available
Wikipedia LinkAdipic acid
NuGOwiki LinkHMDB00448
Metagene LinkHMDB00448
METLIN ID115
PubChem Compound196
PDB ID0L1
ChEBI ID30832
References
Synthesis ReferenceSaito, Kenji. Recovery of adipic acid. Jpn. Kokai Tokkyo Koho (1976), 5 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
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. [1779612 ]
  2. Pettersen JE: In vivo studies on the metabolism of hexanedioic acid. Clin Chim Acta. 1975 Jan 6;58(1):43-50. [1122631 ]
  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. [2026687 ]
  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. [6698061 ]
  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. [429319 ]
  6. Glick N, Fischer M: Adipic aciduria, a dietary artefact. J Inherit Metab Dis. 1991;14(5):849-50. [1779643 ]
  7. Sonmez G, Mutlu H, Ozturk E, Sildiroglu HO, Keskin AT, Basekim CC, Kizilkaya E: Magnetic resonance imaging findings of adult-onset glutaric aciduria type I. Acta Radiol. 2007 Jun;48(5):557-9. [17520433 ]
  8. Liebich HM, Pickert A, Stierle U, Woll J: Gas chromatography-mass spectrometry of saturated and unsaturated dicarboxylic acids in urine. J Chromatogr. 1980 Oct 31;199:181-9. [6778884 ]