Cannabis Compound Database: Showing Compound Card for Oxoadipic acid (CDB004826)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 18:40:45 UTC

Updated at

2020-12-07 19:11:02 UTC

CannabisDB ID

CDB004826

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Oxoadipic acid

Description

Oxoadipic 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Oxoadipate	ChEBI
2-Oxoadipic acid	Kegg
Oxoadipate	Generator
2-Keto-adipate	HMDB
2-Ketoadipate	HMDB
2-Ketoadipic acid	HMDB
2-oxo-Hexanedioate	HMDB
2-oxo-Hexanedioic acid	HMDB
2-Oxohexanedioate	HMDB
2-Oxohexanedioic acid	HMDB
2-Oxohexanedionic acid	HMDB
a-Ketoadipate	HMDB
a-Ketoadipic acid	HMDB
a-Oxoadipate	HMDB
a-Oxoadipic acid	HMDB
alpha-Ketoadipate	HMDB
alpha-Ketoadipic acid	HMDB
alpha-Oxoadipate	HMDB
alpha-Oxoadipic acid	HMDB
α-Ketoadipic acid	HMDB
α-Oxoadipic acid	HMDB

Chemical Formula

C₆H₈O₅

Average Molecular Weight

160.12

Monoisotopic Molecular Weight

160.0372

IUPAC Name

2-oxohexanedioic acid

Traditional Name

oxoadipate

CAS Registry Number

3184-35-8

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 Key

FGSBNBBHOZHUBO-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Medium-chain keto acids and derivatives

Direct Parent

Medium-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 Framework

Aliphatic acyclic compounds

External Descriptors

oxo dicarboxylic acid (CHEBI:15753 )
Dicarboxylic acids (LMFA01170121 )

Ontology

Physiological effect

Health effect:

Health condition:

Aciduria

Metabolism and nutrition disorders:

2-ketoadipic acidemia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Fabaceae

Biological location:

Biofluid and excreta:

Subcellular:

Role

Indirect biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	127 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.37	ALOGPS
logP	0.34	ChemAxon
logS	-0.83	ALOGPS
pKa (Strongest Acidic)	2.84	ChemAxon
pKa (Strongest Basic)	-9.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	33.48 m³·mol⁻¹	ChemAxon
Polarizability	14.16 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Oxoadipic acid, non-derivatized, GC-MS Spectrum	splash10-002b-3910000000-66f39a8b247786a425e6	Spectrum
GC-MS	Oxoadipic acid, non-derivatized, GC-MS Spectrum	splash10-002k-3910000000-977efef811bb47535b80	Spectrum
GC-MS	Oxoadipic acid, non-derivatized, GC-MS Spectrum	splash10-0udr-6900000000-0eb27647b831277a2aef	Spectrum
GC-MS	Oxoadipic acid, non-derivatized, GC-MS Spectrum	splash10-0udr-6900000000-46cd4d782e3d19030993	Spectrum
GC-MS	Oxoadipic acid, non-derivatized, GC-MS Spectrum	splash10-002b-3910000000-66f39a8b247786a425e6	Spectrum
GC-MS	Oxoadipic acid, non-derivatized, GC-MS Spectrum	splash10-002k-3910000000-977efef811bb47535b80	Spectrum
GC-MS	Oxoadipic acid, non-derivatized, GC-MS Spectrum	splash10-0udr-6900000000-0eb27647b831277a2aef	Spectrum
GC-MS	Oxoadipic acid, non-derivatized, GC-MS Spectrum	splash10-0udr-6900000000-46cd4d782e3d19030993	Spectrum
Predicted GC-MS	Oxoadipic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00r6-9300000000-b3f156c173adabf3f1bb	Spectrum
Predicted GC-MS	Oxoadipic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0079-9830000000-a3b1d5e6d378582a6fc2	Spectrum
Predicted GC-MS	Oxoadipic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Oxoadipic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Oxoadipic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Oxoadipic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Oxoadipic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Oxoadipic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Oxoadipic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Oxoadipic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Oxoadipic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Oxoadipic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Oxoadipic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Oxoadipic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Oxoadipic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-0900000000-aef94cc19e461712a097	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0bt9-9500000000-9326906313591bb9da1c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-05db676896bb1e350497	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4l-9000000000-1e566f572b14692461f2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-527da1c1c271db4d8db4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-0a4i-9600000000-38ade0e080ecb7a89588	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-ea231700b469554fcdb4	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9300000000-d69c9552085fc7db91fc	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-052f-9000000000-fa207039b6913600e1b4	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-dc580b3d8a9e58ea79c6	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9200000000-f25470d83f4df952958e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-c524dfcde428d896e041	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-3e6aec4efdb02abcf887	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-2900000000-757eb57780db9df4f78d	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-016v-9700000000-675e5732632f0a0cabe1	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-1da8154067fdb9a27459	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-1900000000-0e26a52af95eb287809d	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-066v-7900000000-d898e0593464c13b3f89	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052g-9100000000-34782bad1c8755ac897d	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014v-9800000000-1b44ce4709a42734f384	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kf-9000000000-e16740a0d326b489193c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-99207abec9ffe380ff34	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0295-5900000000-d4320b8980ff5d5a03d3	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kb-9100000000-27e2c4cbbb4945978dc1	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-bc42e02ad867f6ce85a4	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 500 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Lysine Degradation
Saccharopinuria/Hyperlysinemia II		Not Available
Hyperlysinemia I, Familial		Not Available
Hyperlysinemia II or Saccharopinuria		Not Available
Pyridoxine dependency with seizures		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Dihydrolipoyl dehydrogenase, mitochondrial	DLD	7q31-q32	P09622	details
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	AADAT	4q33	Q8N5Z0	details
2-oxoglutarate dehydrogenase, mitochondrial	OGDH	7p14-p13	Q02218	details
Aminoadipate aminotransferase, isoform CRA_b	AADAT	4q33	Q4W5N8	details
2-oxoglutarate dehydrogenase-like, mitochondrial	OGDHL		Q9ULD0	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000225

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB003362

KNApSAcK ID

C00000770

Chemspider ID

KEGG Compound ID

C00322

BioCyc ID

2K-ADIPATE

BiGG ID

1485244

Wikipedia Link

Not Available

METLIN ID

5234

PubChem Compound

PDB ID

Not Available

ChEBI ID

15753

References

General References

Not Available

Enzymes

Enzyme Details

1. Dihydrolipoyl dehydrogenase, mitochondrial

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

Enzyme Details

2. Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial

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

Enzyme Details

3. 2-oxoglutarate dehydrogenase, mitochondrial

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

Enzyme Details

4. Aminoadipate aminotransferase, isoform CRA_b

General function:: Transcription
Specific function:: Not Available
Gene Name:: AADAT
Uniprot ID:: Q4W5N8
Molecular weight:: 47351.2

Enzyme Details

5. 2-oxoglutarate dehydrogenase-like, mitochondrial

General function:: Involved in oxoglutarate dehydrogenase (succinyl-transferring) activity
Specific function:: Not Available
Gene Name:: OGDHL
Uniprot ID:: Q9ULD0
Molecular weight:: Not Available

Showing Compound Card for Oxoadipic acid (CDB004826)

Structure for CDB004826 (Oxoadipic acid)

Enzymes