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Record Information
Version1.0
Creation Date2016-07-13 19:43:35 UTC
Update Date2016-07-20 21:03:30 UTC
LmdbLMDB00156
Secondary Accession NumbersNone
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
HexanedioateKegg
Hexan-1,6-dicarboxylateKegg
1,4-ButanedicarboxylateGenerator
1,6-HexanedioateGenerator
AdipinateGenerator
Hexanedioic acidGenerator
Hexan-1,6-dicarboxylic acidGenerator
AdipateGenerator
AcifloctinHMDB
AcinettenHMDB
Adi-pureHMDB
AdilactettenHMDB
Kyselina adipovaHMDB
Molten adipateHMDB
Molten adipic acidHMDB
Adipic acid, calcium saltHMDB
Adipic acid, disodium saltHMDB
Sodium adipateHMDB
Adipic acid, cu(+2) saltHMDB
Adipic acid, cu(+2) salt (1:1)HMDB
Adipic acid, diammonium saltHMDB
Adipic acid, sodium saltHMDB
Adipic acid, cu saltHMDB
Adipic acid, potassium saltHMDB
Ammonium adipateHMDB
Magnesium adipateHMDB
Adipic acid, MG salt (1:1)HMDB
Adipic acid, monoammonium saltHMDB
Adipic acid, nickel saltHMDB
Diammonium adipateHMDB
Adipic acidKEGG
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 KeyWNLRTRBMVRJNCN-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity32.74 m³·mol⁻¹ChemAxon
Polarizability14.24 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-03dj-0900000000-5378ec232b7bc8c84368Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-03di-2920000000-a4bb0f67851a49bcd19cSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6u-9000000000-36d8bc2f7d1a77a7b466Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dm-0910000000-596aa8217b629d682b81Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03dj-0900000000-5378ec232b7bc8c84368Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-03di-2920000000-a4bb0f67851a49bcd19cSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03dj-0900000000-60ba84e1d479d88e3facSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-9300000000-c0da1d9e52f67b1d7dbcSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dr-9620000000-9525dd4ed0f987b19a68Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000x-3900000000-1c5a6a5287f8fd7736f1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-001i-9100000000-3e9496a6da881edd91e0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0uea-9500000000-edb5529010e4b88414c4Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-0a6u-9000000000-36d8bc2f7d1a77a7b466Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-a1852cfc66b4feae9b18Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0ue9-6900000000-90e783cc3522f0ce7880Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-9200000000-b5a64d560d8bc62d8d51Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001i-9000000000-a96d5ee9551b944e4db8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001i-9000000000-2e61b7d2a4dbc9867123Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-a1852cfc66b4feae9b18Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0ue9-6900000000-90e783cc3522f0ce7880Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-9200000000-b5a64d560d8bc62d8d51Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-9000000000-a96d5ee9551b944e4db8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-9000000000-2e61b7d2a4dbc9867123Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-2900000000-983aa19fb3183a9bc5abSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0ue9-8900000000-a976da84fb798bd80a34Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0n33-9100000000-8ed018879ca3f86cd379Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9300000000-c6cf63d45cff0205c31aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-001i-9200000000-9d33c5f6441e75071938Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0900000000-ece39ae1f752cf2970f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fba-5900000000-682fc79230e6f03bacfbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-66b61bf2c65c15bb7fedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-ec5d2c95f1dac5349608Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-2900000000-27613c7de7a721350bb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9100000000-78804e4122c63b62ca5bSpectrum
MSMass Spectrum (Electron Ionization)splash10-0f6x-9200000000-988f76bb42297a8d9d3bSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Plasma
  • Ruminal Fluid
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableCaprine details
DrugBank IDNot Available
HMDB IDHMDB0000448
FooDB IDFDB008309
Phenol Explorer IDNot Available
KNApSAcK IDC00001178
BiGG IDNot Available
BioCyc IDADIPATE
METLIN ID115
PDB IDNot Available
Wikipedia LinkAdipic_acid
Chemspider ID191
ChEBI ID30832
PubChem Compound ID196
Kegg Compound IDC06104
YMDB IDNot Available
ECMDB IDECMDB02973
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Glick N, Fischer M: Adipic aciduria, a dietary artefact. J Inherit Metab Dis. 1991;14(5):849-50. [1779643 ]
  2. 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 ]
  3. 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 ]