Record Information
Version1.0
Created at2020-04-17 18:36:00 UTC
Updated at2020-11-18 16:38:39 UTC
CannabisDB IDCDB004780
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2-Ketobutyric acid
Description2-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
Thumb
Synonyms
ValueSource
2-Ketobutanoic acidChEBI
2-Oxobutyric acidChEBI
3-Methyl pyruvic acidChEBI
alpha-KetobutyrateChEBI
alpha-Ketobutyric acidChEBI
alpha-oxo-N-Butyric acidChEBI
2-OxobutyrateKegg
2-Oxobutanoic acidKegg
2-KetobutanoateGenerator
3-Methyl pyruvateGenerator
a-KetobutyrateGenerator
a-Ketobutyric acidGenerator
Α-ketobutyrateGenerator
Α-ketobutyric acidGenerator
a-oxo-N-ButyrateGenerator
a-oxo-N-Butyric acidGenerator
alpha-oxo-N-ButyrateGenerator
Α-oxo-N-butyrateGenerator
Α-oxo-N-butyric acidGenerator
2-OxobutanoateGenerator
2-KetobutyrateGenerator
2-oxo-ButanoateHMDB
2-oxo-Butanoic acidHMDB
2-oxo-ButyrateHMDB
2-oxo-Butyric acidHMDB
2-oxo-N-ButyrateHMDB
2-oxo-N-Butyric acidHMDB
3-MethylpyruvateHMDB
3-Methylpyruvic acidHMDB
a-Keto-N-butyrateHMDB
a-Keto-N-butyric acidHMDB
a-OxobutyrateHMDB
a-Oxobutyric acidHMDB
alpha-Keto-N-butyrateHMDB
alpha-Keto-N-butyric acidHMDB
alpha-Ketobutric acidHMDB
alpha-OxobutyrateHMDB
alpha-Oxobutyric acidHMDB
Methyl-pyruvateHMDB
Methyl-pyruvic acidHMDB
Propionyl-formateHMDB
Propionyl-formic acidHMDB
alpha-Ketobutyric acid, sodium saltHMDB
2-Ketobutyric acidChEBI
Chemical FormulaC4H6O3
Average Molecular Weight102.09
Monoisotopic Molecular Weight102.0317
IUPAC Name2-oxobutanoic acid
Traditional Name2-oxobutanoic acid
CAS Registry Number600-18-0
SMILES
CCC(=O)C(O)=O
InChI Identifier
InChI=1S/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7)
InChI KeyTYEYBOSBBBHJIV-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point33 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility119 mg/mLNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.07ALOGPS
logP0.77ChemAxon
logS-0.11ALOGPS
pKa (Strongest Acidic)3.19ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.62 m³·mol⁻¹ChemAxon
Polarizability9.2 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS2-Ketobutyric acid, non-derivatized, GC-MS Spectrumsplash10-0gbj-1900000000-8daa299f5bc38a7f9b3eSpectrum
GC-MS2-Ketobutyric acid, non-derivatized, GC-MS Spectrumsplash10-014s-1910000000-d01bcd7b41fdcc634eeaSpectrum
GC-MS2-Ketobutyric acid, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-000i-9200000000-3b3816ffee5771215904Spectrum
GC-MS2-Ketobutyric acid, 1 MEOX; 1 TMS, GC-MS Spectrumsplash10-000i-6910000000-5b264d5f7e53f3e80b12Spectrum
GC-MS2-Ketobutyric acid, 2 TMS, GC-MS Spectrumsplash10-001i-6950000000-db7f6a0f03a8cce59baeSpectrum
GC-MS2-Ketobutyric acid, non-derivatized, GC-MS Spectrumsplash10-0ftb-0920000000-a6c93d8761ef15f7f7d4Spectrum
GC-MS2-Ketobutyric acid, non-derivatized, GC-MS Spectrumsplash10-014i-0920000000-406fe70e72dbd9c3f274Spectrum
GC-MS2-Ketobutyric acid, non-derivatized, GC-MS Spectrumsplash10-0gbj-1900000000-8daa299f5bc38a7f9b3eSpectrum
GC-MS2-Ketobutyric acid, non-derivatized, GC-MS Spectrumsplash10-014s-1910000000-d01bcd7b41fdcc634eeaSpectrum
GC-MS2-Ketobutyric acid, non-derivatized, GC-MS Spectrumsplash10-000i-9200000000-3b3816ffee5771215904Spectrum
GC-MS2-Ketobutyric acid, non-derivatized, GC-MS Spectrumsplash10-000i-6910000000-5b264d5f7e53f3e80b12Spectrum
GC-MS2-Ketobutyric acid, non-derivatized, GC-MS Spectrumsplash10-001i-6950000000-db7f6a0f03a8cce59baeSpectrum
GC-MS2-Ketobutyric acid, non-derivatized, GC-MS Spectrumsplash10-000i-8900000000-97bab6630de4df095a7fSpectrum
GC-MS2-Ketobutyric acid, non-derivatized, GC-MS Spectrumsplash10-000i-9200000000-0ebb2354fe3f935fe177Spectrum
Predicted GC-MS2-Ketobutyric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a6r-9000000000-32269ef3ef778c482f99Spectrum
Predicted GC-MS2-Ketobutyric acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0adi-9200000000-f92941e9f326d8ccf3e4Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0pb9-9600000000-53ebb7164f74d7d92a4dSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0zfr-5900000000-1db864754705beb79b55Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0udi-9800000000-5ba5b9ede5b1bc389b87Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0900000000-bfdcad5bc3ed586bdedeSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0900000000-bfdcad5bc3ed586bdedeSpectrum
MS/MSLC-MS/MS Spectrum - QqQ 4V, positivesplash10-0pb9-9600000000-b10635fbec5572d4d084Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 8V, positivesplash10-0a4i-9100000000-4c5e7d24dca6677e1570Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 12V, positivesplash10-0a4i-9000000000-ded44cfcbe7960954fdfSpectrum
MS/MSLC-MS/MS Spectrum - QqQ 16V, positivesplash10-0a4i-9000000000-1b350be7438b08f1946aSpectrum
MS/MSLC-MS/MS Spectrum - QqQ 20V, positivesplash10-056r-9000000000-172a175b8b9ebfd5529fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0k9i-9400000000-0061f4635858d851f127Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9100000000-b943445194fb5f8e3a0fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-bc5920b9bd140be6b06dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-5900000000-f7dfb4554f0b9e1499c9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-9200000000-e54106ad5bf45a9f072cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-7bbba57578cf720974e3Spectrum
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
Pyruvate dehydrogenase E1 component subunit beta, mitochondrialPDHB3p21.1-p14.2P11177 details
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrialPDHA1Xp22.1P08559 details
Pyruvate dehydrogenase E1 component subunit alpha, testis-specific form, mitochondrialPDHA24q22-q23P29803 details
2-oxoisovalerate dehydrogenase subunit beta, mitochondrialBCKDHB6q14.1P21953 details
2-oxoisovalerate dehydrogenase subunit alpha, mitochondrialBCKDHA19q13.1-q13.2P12694 details
2-oxoglutarate dehydrogenase, mitochondrialOGDH7p14-p13Q02218 details
Cystathionine gamma-lyaseCTH1p31.1P32929 details
L-serine dehydratase/L-threonine deaminaseSDS12q24.13P20132 details
L-lactate dehydrogenase A-like 6ALDHAL6A11p15.1Q6ZMR3 details
Urocanate hydrataseUROC13q21.3Q96N76 details
[3-methyl-2-oxobutanoate dehydrogenase [lipoamide]] kinase, mitochondrialBCKDK16p11.2O14874 details
L-lactate dehydrogenase B chainLDHB12p12.2-p12.1P07195 details
L-lactate dehydrogenase C chainLDHC11p15.1P07864 details
L-lactate dehydrogenase A chainLDHA11p15.4P00338 details
L-lactate dehydrogenase A-like 6BLDHAL6B15q22.2Q9BYZ2 details
Trimethyllysine dioxygenase, mitochondrialTMLHEXq28Q9NVH6 details
Alpha-ketoglutarate-dependent dioxygenase alkB homolog 2ALKBH212q24.11Q6NS38 details
Alpha-ketoglutarate-dependent dioxygenase alkB homolog 3ALKBH311p11.2Q96Q83 details
Serine dehydratase-likeSDSL12q24.13Q96GA7 details
2-oxoglutarate dehydrogenase-like, mitochondrialOGDHLQ9ULD0 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
2-oxoisovalerate dehydrogenase subunit alpha, mitochondrialBCKDHA19q13.1-q13.2P12694 details
Trimethyllysine dioxygenase, mitochondrialTMLHEXq28Q9NVH6 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
2-oxoglutarate receptor 1OXGR113q32.1Q96P68 details
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Cystathionine gamma-lyaseCTH1p31.1P32929 details
Concentrations Data
Not Available
HMDB IDHMDB0000005
DrugBank IDDB04553
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030356
KNApSAcK IDC00019675
Chemspider ID57
KEGG Compound IDC00109
BioCyc ID2-OXOBUTANOATE
BiGG ID33889
Wikipedia LinkAlpha-Ketobutyric_acid
METLIN IDNot Available
PubChem Compound58
PDB IDNot Available
ChEBI ID30831
References
General ReferencesNot Available

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

Enzymes

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