Cannabis Compound Database: Showing Compound Card for 2-Ketobutyric acid (CDB004780)

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Record Information

Version

1.0

Created at

2020-04-17 18:36:00 UTC

Updated at

2020-11-18 16:38:39 UTC

CannabisDB ID

CDB004780

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

2-Ketobutyric acid

Description

2-Ketobutyric acid, also known as alpha-ketobutyrate or 2-oxobutyrate, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. 2-Ketobutyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Ketobutyric acid exists in all living species, ranging from bacteria to humans. Within humans, 2-ketobutyric acid participates in a number of enzymatic reactions. In particular, 2-ketobutyric acid can be biosynthesized from L-threonine; which is mediated by the enzyme L-serine dehydratase/l-threonine deaminase. In addition, 2-ketobutyric acid and coenzyme A can be converted into propionyl-CoA; which is mediated by the enzyme branched-chain alpha-keto dehydrogenase complex. In humans, 2-ketobutyric acid is involved in threonine and 2-oxobutanoate degradation. Outside of the human body, 2-Ketobutyric acid has been detected, but not quantified in, several different foods, such as black crowberries, lima beans, lettuces, oxheart cabbages, and grass pea. This could make 2-ketobutyric acid a potential biomarker for the consumption of these foods. A 2-oxo monocarboxylic acid that is the 2-oxo derivative of butanoic acid. 2-Ketobutyric 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-Ketobutanoic acid	ChEBI
2-Oxobutyric acid	ChEBI
3-Methyl pyruvic acid	ChEBI
alpha-Ketobutyrate	ChEBI
alpha-Ketobutyric acid	ChEBI
alpha-oxo-N-Butyric acid	ChEBI
2-Oxobutyrate	Kegg
2-Oxobutanoic acid	Kegg
2-Ketobutanoate	Generator
3-Methyl pyruvate	Generator
a-Ketobutyrate	Generator
a-Ketobutyric acid	Generator
Α-ketobutyrate	Generator
Α-ketobutyric acid	Generator
a-oxo-N-Butyrate	Generator
a-oxo-N-Butyric acid	Generator
alpha-oxo-N-Butyrate	Generator
Α-oxo-N-butyrate	Generator
Α-oxo-N-butyric acid	Generator
2-Oxobutanoate	Generator
2-Ketobutyrate	Generator
2-oxo-Butanoate	HMDB
2-oxo-Butanoic acid	HMDB
2-oxo-Butyrate	HMDB
2-oxo-Butyric acid	HMDB
2-oxo-N-Butyrate	HMDB
2-oxo-N-Butyric acid	HMDB
3-Methylpyruvate	HMDB
3-Methylpyruvic acid	HMDB
a-Keto-N-butyrate	HMDB
a-Keto-N-butyric acid	HMDB
a-Oxobutyrate	HMDB
a-Oxobutyric acid	HMDB
alpha-Keto-N-butyrate	HMDB
alpha-Keto-N-butyric acid	HMDB
alpha-Ketobutric acid	HMDB
alpha-Oxobutyrate	HMDB
alpha-Oxobutyric acid	HMDB
Methyl-pyruvate	HMDB
Methyl-pyruvic acid	HMDB
Propionyl-formate	HMDB
Propionyl-formic acid	HMDB
alpha-Ketobutyric acid, sodium salt	HMDB
2-Ketobutyric acid	ChEBI

Chemical Formula

C₄H₆O₃

Average Molecular Weight

102.09

Monoisotopic Molecular Weight

102.0317

IUPAC Name

2-oxobutanoic acid

Traditional Name

2-oxobutanoic acid

CAS Registry Number

600-18-0

SMILES

CCC(=O)C(O)=O

InChI Identifier

InChI=1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7)

InChI Key

TYEYBOSBBBHJIV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Short-chain keto acids and derivatives

Direct Parent

Short-chain keto acids and derivatives

Alternative Parents

Substituents

Short-chain keto acid
Alpha-keto acid
Alpha-hydroxy ketone
Ketone
Monocarboxylic acid or derivatives
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

2-oxo monocarboxylic acid (CHEBI:30831 )
short-chain fatty acid (CHEBI:30831 )
Oxo fatty acids (C00109 )
Oxo fatty acids (LMFA01060002 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Biofluid and excreta:

Subcellular:

Cytoplasm

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	33 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	119 mg/mL	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.07	ALOGPS
logP	0.77	ChemAxon
logS	-0.11	ALOGPS
pKa (Strongest Acidic)	3.19	ChemAxon
pKa (Strongest Basic)	-9.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	22.62 m³·mol⁻¹	ChemAxon
Polarizability	9.2 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	2-Ketobutyric acid, non-derivatized, GC-MS Spectrum	splash10-0gbj-1900000000-8daa299f5bc38a7f9b3e	Spectrum
GC-MS	2-Ketobutyric acid, non-derivatized, GC-MS Spectrum	splash10-014s-1910000000-d01bcd7b41fdcc634eea	Spectrum
GC-MS	2-Ketobutyric acid, 1 MEOX; 1 TMS, GC-MS Spectrum	splash10-000i-9200000000-3b3816ffee5771215904	Spectrum
GC-MS	2-Ketobutyric acid, 1 MEOX; 1 TMS, GC-MS Spectrum	splash10-000i-6910000000-5b264d5f7e53f3e80b12	Spectrum
GC-MS	2-Ketobutyric acid, 2 TMS, GC-MS Spectrum	splash10-001i-6950000000-db7f6a0f03a8cce59bae	Spectrum
GC-MS	2-Ketobutyric acid, non-derivatized, GC-MS Spectrum	splash10-0ftb-0920000000-a6c93d8761ef15f7f7d4	Spectrum
GC-MS	2-Ketobutyric acid, non-derivatized, GC-MS Spectrum	splash10-014i-0920000000-406fe70e72dbd9c3f274	Spectrum
GC-MS	2-Ketobutyric acid, non-derivatized, GC-MS Spectrum	splash10-0gbj-1900000000-8daa299f5bc38a7f9b3e	Spectrum
GC-MS	2-Ketobutyric acid, non-derivatized, GC-MS Spectrum	splash10-014s-1910000000-d01bcd7b41fdcc634eea	Spectrum
GC-MS	2-Ketobutyric acid, non-derivatized, GC-MS Spectrum	splash10-000i-9200000000-3b3816ffee5771215904	Spectrum
GC-MS	2-Ketobutyric acid, non-derivatized, GC-MS Spectrum	splash10-000i-6910000000-5b264d5f7e53f3e80b12	Spectrum
GC-MS	2-Ketobutyric acid, non-derivatized, GC-MS Spectrum	splash10-001i-6950000000-db7f6a0f03a8cce59bae	Spectrum
GC-MS	2-Ketobutyric acid, non-derivatized, GC-MS Spectrum	splash10-000i-8900000000-97bab6630de4df095a7f	Spectrum
GC-MS	2-Ketobutyric acid, non-derivatized, GC-MS Spectrum	splash10-000i-9200000000-0ebb2354fe3f935fe177	Spectrum
Predicted GC-MS	2-Ketobutyric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a6r-9000000000-32269ef3ef778c482f99	Spectrum
Predicted GC-MS	2-Ketobutyric acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0adi-9200000000-f92941e9f326d8ccf3e4	Spectrum
Predicted GC-MS	2-Ketobutyric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Ketobutyric acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Ketobutyric acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	2-Ketobutyric acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0pb9-9600000000-53ebb7164f74d7d92a4d	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0zfr-5900000000-1db864754705beb79b55	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0udi-9800000000-5ba5b9ede5b1bc389b87	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0udi-0900000000-bfdcad5bc3ed586bdede	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0900000000-bfdcad5bc3ed586bdede	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 4V, positive	splash10-0pb9-9600000000-b10635fbec5572d4d084	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 8V, positive	splash10-0a4i-9100000000-4c5e7d24dca6677e1570	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 12V, positive	splash10-0a4i-9000000000-ded44cfcbe7960954fdf	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 16V, positive	splash10-0a4i-9000000000-1b350be7438b08f1946a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 20V, positive	splash10-056r-9000000000-172a175b8b9ebfd5529f	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0k9i-9400000000-0061f4635858d851f127	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-9100000000-b943445194fb5f8e3a0f	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-bc5920b9bd140be6b06d	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-5900000000-f7dfb4554f0b9e1499c9	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a59-9200000000-e54106ad5bf45a9f072c	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-7bbba57578cf720974e3	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-ca1ed9c5aadcbdabc2a3	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-aced8e004436190f07b7	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-a3d7ddf227bd6aa91a54	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0pb9-9700000000-503296025148ec314383	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-933b567955b5de5b1744	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-7d9db52021fefc87a855	2021-09-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Methionine Metabolism
Glycine and Serine Metabolism
Threonine and 2-Oxobutanoate Degradation		Not Available
Homocysteine Degradation		Not Available
Selenoamino Acid Metabolism

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Pyruvate dehydrogenase E1 component subunit beta, mitochondrial	PDHB	3p21.1-p14.2	P11177	details
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial	PDHA1	Xp22.1	P08559	details
Pyruvate dehydrogenase E1 component subunit alpha, testis-specific form, mitochondrial	PDHA2	4q22-q23	P29803	details
2-oxoisovalerate dehydrogenase subunit beta, mitochondrial	BCKDHB	6q14.1	P21953	details
2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial	BCKDHA	19q13.1-q13.2	P12694	details
2-oxoglutarate dehydrogenase, mitochondrial	OGDH	7p14-p13	Q02218	details
Cystathionine gamma-lyase	CTH	1p31.1	P32929	details
L-serine dehydratase/L-threonine deaminase	SDS	12q24.13	P20132	details
L-lactate dehydrogenase A-like 6A	LDHAL6A	11p15.1	Q6ZMR3	details
Urocanate hydratase	UROC1	3q21.3	Q96N76	details
[3-methyl-2-oxobutanoate dehydrogenase [lipoamide]] kinase, mitochondrial	BCKDK	16p11.2	O14874	details
L-lactate dehydrogenase B chain	LDHB	12p12.2-p12.1	P07195	details
L-lactate dehydrogenase C chain	LDHC	11p15.1	P07864	details
L-lactate dehydrogenase A chain	LDHA	11p15.4	P00338	details
L-lactate dehydrogenase A-like 6B	LDHAL6B	15q22.2	Q9BYZ2	details
Trimethyllysine dioxygenase, mitochondrial	TMLHE	Xq28	Q9NVH6	details
Alpha-ketoglutarate-dependent dioxygenase alkB homolog 2	ALKBH2	12q24.11	Q6NS38	details
Alpha-ketoglutarate-dependent dioxygenase alkB homolog 3	ALKBH3	11p11.2	Q96Q83	details
Serine dehydratase-like	SDSL	12q24.13	Q96GA7	details
2-oxoglutarate dehydrogenase-like, mitochondrial	OGDHL		Q9ULD0	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial	BCKDHA	19q13.1-q13.2	P12694	details
Trimethyllysine dioxygenase, mitochondrial	TMLHE	Xq28	Q9NVH6	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
2-oxoglutarate receptor 1	OXGR1	13q32.1	Q96P68	details

Transcriptional Factors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Cystathionine gamma-lyase	CTH	1p31.1	P32929	details

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000005

DrugBank ID

DB04553

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB030356

KNApSAcK ID

C00019675

Chemspider ID

KEGG Compound ID

C00109

BioCyc ID

2-OXOBUTANOATE

BiGG ID

33889

Wikipedia Link

Alpha-Ketobutyric_acid

METLIN ID

Not Available

PubChem Compound

PDB ID

Not Available

ChEBI ID

30831

References

General References

Not Available

Only showing the first 10 proteins. There are 24 proteins in total.

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Enzymes

Enzyme Details

1. Pyruvate dehydrogenase E1 component subunit beta, mitochondrial

General function:: Involved in catalytic activity
Specific function:: The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:: PDHB
Uniprot ID:: P11177
Molecular weight:: 39233.1

Enzyme Details

2. Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial

General function:: Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
Specific function:: The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:: PDHA1
Uniprot ID:: P08559
Molecular weight:: 43295.255

Enzyme Details

3. Pyruvate dehydrogenase E1 component subunit alpha, testis-specific form, mitochondrial

General function:: Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
Specific function:: The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:: PDHA2
Uniprot ID:: P29803
Molecular weight:: 42932.855

Enzyme Details

4. 2-oxoisovalerate dehydrogenase subunit beta, mitochondrial

General function:: Involved in catalytic activity
Specific function:: The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:: BCKDHB
Uniprot ID:: P21953
Molecular weight:: 43122.065

Enzyme Details

5. 2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial

General function:: Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
Specific function:: The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:: BCKDHA
Uniprot ID:: P12694
Molecular weight:: 50470.58

Enzyme Details

6. 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

7. Cystathionine gamma-lyase

General function:: Involved in pyridoxal phosphate binding
Specific function:: Catalyzes the last step in the trans-sulfuration pathway from methionine to cysteine. Has broad substrate specificity. Converts cystathionine to cysteine, ammonia and 2-oxobutanoate. Converts two cysteine molecules to lanthionine and hydrogen sulfide. Can also accept homocysteine as substrate. Specificity depends on the levels of the endogenous substrates. Generates the endogenous signaling molecule hydrogen sulfide (H2S), and so contributes to the regulation of blood pressure. Acts as a cysteine-protein sulfhydrase by mediating sulfhydration of target proteins: sulfhydration consists of converting -SH groups into -SSH on specific cysteine residues of target proteins such as GAPDH, PTPN1 and NF-kappa-B subunit RELA, thereby regulating their function.
Gene Name:: CTH
Uniprot ID:: P32929
Molecular weight:: 41259.91

Enzyme Details

8. L-serine dehydratase/L-threonine deaminase

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: SDS
Uniprot ID:: P20132
Molecular weight:: 34625.105

Enzyme Details

9. L-lactate dehydrogenase A-like 6A

General function:: Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:: Displays an lactate dehydrogenase activity. Significantly increases the transcriptional activity of JUN, when overexpressed.
Gene Name:: LDHAL6A
Uniprot ID:: Q6ZMR3
Molecular weight:: 36507.015

Enzyme Details

10. Urocanate hydratase

General function:: Involved in urocanate hydratase activity
Specific function:: Not Available
Gene Name:: UROC1
Uniprot ID:: Q96N76
Molecular weight:: 80911.275

Only showing the first 10 proteins. There are 24 proteins in total.

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Showing Compound Card for 2-Ketobutyric acid (CDB004780)

Structure for CDB004780 (2-Ketobutyric acid)

Enzymes