Record Information
Version1.0
Created at2020-04-17 18:40:45 UTC
Updated at2020-12-07 19:11:02 UTC
CannabisDB IDCDB004826
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameOxoadipic acid
DescriptionOxoadipic acid, also known as 2-oxoadipate or a-ketoadipate, belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. Oxoadipic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Oxoadipic acid exists in all living species, ranging from bacteria to humans. Within humans, oxoadipic acid participates in a number of enzymatic reactions. In particular, oxoadipic acid and L-glutamic acid can be biosynthesized from aminoadipic acid and oxoglutaric acid through its interaction with the enzyme kynurenine/alpha-aminoadipate aminotransferase, mitochondrial. In addition, oxoadipic acid can be converted into carbon dioxide through the action of the enzyme oxoglutarate dehydrogenase complex. In humans, oxoadipic acid is involved in the metabolic disorder called 2-aminoadipic 2-oxoadipic aciduria. Outside of the human body, Oxoadipic acid has been detected, but not quantified in, pulses. This could make oxoadipic acid a potential biomarker for the consumption of these foods. Oxoadipic acid is a potentially toxic compound. Oxoadipic acid, with regard to humans, has been linked to several inborn metabolic disorders including 2-aminoadipic aciduria, alpha-aminoadipic aciduria, and 2-ketoadipic acidemia. An oxo dicarboxylic acid that is adipic acid substituted by an oxo group at position 2. Oxoadipic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
2-OxoadipateChEBI
2-Oxoadipic acidKegg
OxoadipateGenerator
2-Keto-adipateHMDB
2-KetoadipateHMDB
2-Ketoadipic acidHMDB
2-oxo-HexanedioateHMDB
2-oxo-Hexanedioic acidHMDB
2-OxohexanedioateHMDB
2-Oxohexanedioic acidHMDB
2-Oxohexanedionic acidHMDB
a-KetoadipateHMDB
a-Ketoadipic acidHMDB
a-OxoadipateHMDB
a-Oxoadipic acidHMDB
alpha-KetoadipateHMDB
alpha-Ketoadipic acidHMDB
alpha-OxoadipateHMDB
alpha-Oxoadipic acidHMDB
α-Ketoadipic acidHMDB
α-Oxoadipic acidHMDB
Chemical FormulaC6H8O5
Average Molecular Weight160.12
Monoisotopic Molecular Weight160.0372
IUPAC Name2-oxohexanedioic acid
Traditional Nameoxoadipate
CAS Registry Number3184-35-8
SMILES
OC(=O)CCCC(=O)C(O)=O
InChI Identifier
InChI=1S/C6H8O5/c7-4(6(10)11)2-1-3-5(8)9/h1-3H2,(H,8,9)(H,10,11)
InChI KeyFGSBNBBHOZHUBO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassMedium-chain keto acids and derivatives
Direct ParentMedium-chain keto acids and derivatives
Alternative Parents
Substituents
  • Medium-chain keto acid
  • Dicarboxylic acid or derivatives
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • 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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point127 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.37ALOGPS
logP0.34ChemAxon
logS-0.83ALOGPS
pKa (Strongest Acidic)2.84ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity33.48 m³·mol⁻¹ChemAxon
Polarizability14.16 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSOxoadipic acid, non-derivatized, GC-MS Spectrumsplash10-002b-3910000000-66f39a8b247786a425e6Spectrum
GC-MSOxoadipic acid, non-derivatized, GC-MS Spectrumsplash10-002k-3910000000-977efef811bb47535b80Spectrum
GC-MSOxoadipic acid, non-derivatized, GC-MS Spectrumsplash10-0udr-6900000000-0eb27647b831277a2aefSpectrum
GC-MSOxoadipic acid, non-derivatized, GC-MS Spectrumsplash10-0udr-6900000000-46cd4d782e3d19030993Spectrum
GC-MSOxoadipic acid, non-derivatized, GC-MS Spectrumsplash10-002b-3910000000-66f39a8b247786a425e6Spectrum
GC-MSOxoadipic acid, non-derivatized, GC-MS Spectrumsplash10-002k-3910000000-977efef811bb47535b80Spectrum
GC-MSOxoadipic acid, non-derivatized, GC-MS Spectrumsplash10-0udr-6900000000-0eb27647b831277a2aefSpectrum
GC-MSOxoadipic acid, non-derivatized, GC-MS Spectrumsplash10-0udr-6900000000-46cd4d782e3d19030993Spectrum
Predicted GC-MSOxoadipic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00r6-9300000000-b3f156c173adabf3f1bbSpectrum
Predicted GC-MSOxoadipic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-9830000000-a3b1d5e6d378582a6fc2Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0900000000-aef94cc19e461712a097Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0bt9-9500000000-9326906313591bb9da1cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-05db676896bb1e350497Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9000000000-1e566f572b14692461f2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-527da1c1c271db4d8db4Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0a4i-9600000000-38ade0e080ecb7a89588Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-2900000000-757eb57780db9df4f78dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016v-9700000000-675e5732632f0a0cabe1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-1da8154067fdb9a27459Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1900000000-0e26a52af95eb287809dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066v-7900000000-d898e0593464c13b3f89Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052g-9100000000-34782bad1c8755ac897dSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Dihydrolipoyl dehydrogenase, mitochondrialDLD7q31-q32P09622 details
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrialAADAT4q33Q8N5Z0 details
2-oxoglutarate dehydrogenase, mitochondrialOGDH7p14-p13Q02218 details
Aminoadipate aminotransferase, isoform CRA_bAADAT4q33Q4W5N8 details
2-oxoglutarate dehydrogenase-like, mitochondrialOGDHLQ9ULD0 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000225
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003362
KNApSAcK IDC00000770
Chemspider ID70
KEGG Compound IDC00322
BioCyc ID2K-ADIPATE
BiGG ID1485244
Wikipedia LinkNot Available
METLIN ID5234
PubChem Compound71
PDB IDNot Available
ChEBI ID15753
References
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Lipoamide dehydrogenase is a component of the glycine cleavage system as well as of the alpha-ketoacid dehydrogenase complexes. Involved in the hyperactivation of spermatazoa during capacitation and in the spermatazoal acrosome reaction.
Gene Name:
DLD
Uniprot ID:
P09622
Molecular weight:
54176.91
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Transaminase with broad substrate specificity. Has transaminase activity towards aminoadipate, kynurenine, methionine and glutamate. Shows activity also towards tryptophan, aspartate and hydroxykynurenine. Accepts a variety of oxo-acids as amino-group acceptors, with a preference for 2-oxoglutarate, 2-oxocaproic acid, phenylpyruvate and alpha-oxo-gamma-methiol butyric acid. Can also use glyoxylate as amino-group acceptor (in vitro).
Gene Name:
AADAT
Uniprot ID:
Q8N5Z0
Molecular weight:
47351.17
General function:
Involved in oxoglutarate dehydrogenase (succinyl-transferring) activity
Specific function:
The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). It contains multiple copies of three enzymatic components: 2-oxoglutarate dehydrogenase (E1), dihydrolipoamide succinyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
OGDH
Uniprot ID:
Q02218
Molecular weight:
48179.59
General function:
Transcription
Specific function:
Not Available
Gene Name:
AADAT
Uniprot ID:
Q4W5N8
Molecular weight:
47351.2
General function:
Involved in oxoglutarate dehydrogenase (succinyl-transferring) activity
Specific function:
Not Available
Gene Name:
OGDHL
Uniprot ID:
Q9ULD0
Molecular weight:
Not Available