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Bovine Metabolome Database



Showing metabocard for 2-Ketobutyric acid (BMDB00005)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-28 10:06:09
Accession Number BMDB00005
Common Name 2-Ketobutyric acid
Description 2-Ketobutyric acid is a substance that is involved in the metabolism of many amino acids (glycine, methionine, valine, leucine, serine, threonine, isoleucine) as well as propanoate metabolism and C-5 branched dibasic acid metabolism. More specifically, alpha-ketobutyric acid is a product of the lysis of cystathionine. It is also one of the degradation products of threonine. It can be converted to propionyl-CoA (and subsequently methylmalonyl CoA, which can be converted to succinyl CoA, a citric acid cycle intermediate), and thus enter the citric acid cycle.
Synonyms
  1. 2-Ketobutanoate
  2. 2-Ketobutanoic acid
  3. 2-Oxo-Butanoate
  4. 2-Oxo-Butanoic acid
  5. 2-Oxo-n-butyrate
  6. 2-Oxo-n-butyric acid
  7. 2-Oxobutanoate
  8. 2-Oxobutanoic acid
  9. 2-Oxobutyrate
  10. 2-Oxobutyric acid
  11. 2-oxo-Butyrate
  12. 2-oxo-Butyric acid
  13. 3-Methylpyruvate
  14. 3-Methylpyruvic acid
  15. alpha-Keto-n-butyrate
  16. alpha-Keto-n-butyric acid
  17. alpha-Ketobutyrate
  18. alpha-Ketobutric acid
  19. alpha-Ketobutyric acid
  20. alpha-Oxo-n-butyrate
  21. alpha-Oxo-n-butyric acid
  22. alpha-Oxobutyrate
  23. a-Ketobutyrate
  24. a-Ketobutyric acid
  25. a-Oxo-n-butyrate
  26. a-Oxo-n-butyric acid
  27. a-Oxobutyrate
  28. a-Oxobutyric acid
  29. a-keto-n-Butyrate
  30. a-keto-n-Butyric acid
  31. methyl-Pyruvate
  32. methyl-Pyruvic acid
  33. propionyl-formate
  34. propionyl-formic acid
  35. alpha-Oxobutyric acid
Chemical IUPAC Name 2-oxobutanoic acid
Chemical Formula C4H6O3
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Keto-Acids
Sub Class
  • Short chain keto-acids
Family
  • Mammalian_Metabolite
Species
  • ketone; carboxylic acid
Biofunction
  • Component of Cysteine metabolism; Component of Glycine, serine and threonine metabolism; Component of Methionine metabolism; Component of Nitrogen metabolism; Component of Selenoamino acid metabolism
Application
Source
  • Endogenous
Average Molecular Weight 102.089
Monoisotopic Molecular Weight 102.031693
Isomeric SMILES CCC(=O)C(O)=O
Canonical SMILES CCC(=O)C(O)=O
KEGG Compound ID C00109 Link Image
BioCyc ID 2-OXOBUTANOATE Link Image
BiGG ID 33889 Link Image
Wikipedia Link Alpha-ketobutyric_acid Link Image
METLIN ID Not Available
PubChem Compound 58 Link Image
PubChem Substance 3133599 Link Image
ChEBI ID 16763 Link Image
CAS Registry Number 600-18-0
InChI Identifier InChI=1/C4H6O3/c1-2-3(5)4(6)7/h2H2,1H3,(H,6,7)
Synthesis Reference Figge, Rainer; Lux, Fabien; Raynaud, Celine; Soucaille, Philippe. Production of a-ketobutyrate by engineered Escherichia coli.PCT Int. Appl. (2006), 31pp.
Melting Point (Experimental) 33oC [Suante, H.; Oxidation Communications 2004, V27(2), P344-348]
Experimental Water Solubility 119 mg/mL [HMP experimental] Source: PhysProp
Predicted Water Solubility 1000.0 mg/mL [MEYLAN,WM et al. (1996)]; 79.2 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 0.07 [Predicted by ALOGPS]; -0.2 [Predicted by PubChem via XLOGP]; -0.75 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
Download File
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Medium Energy
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High Energy
Download File
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Glycine, Serine and Threonine Metabolism
  • Methionine Metabolism
  • Propanoate Metabolism
HMDB Pathways
Name Glycine, Serine and Threonine Metabolism
Image Show Link Image
Name Methionine Metabolism
Image Show Link Image
Name Propanoate Metabolism
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KEGG Pathways
Name Glycine, Serine and Threonine Metabolism
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Name Methionine Metabolism
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Name Propanoate Metabolism
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SimCell Pathways
Name Glycine, Serine and Threonine Metabolism
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Graph Show Link Image
SBML Download (XML) Link Image
Name Methionine Metabolism
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SBML Download (XML) Link Image
Name Propanoate Metabolism
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Graph
SBML
General References
  1. Wikipedia Link Image
Metabolic Enzymes
  1. L-serine dehydratase
  2. Cystathionine gamma-lyase
Enzyme 1 [top]
Enzyme 1 ID 88
Enzyme 1 Name L-serine dehydratase
Enzyme 1 Synonyms
  1. L-serine deaminase
Enzyme 1 Gene Name SDS
Enzyme 1 Protein Sequence >L-serine dehydratase
MMSGRPLHMETPVRDSMTLSKVAGTTAYLKLDSAQPSGSFKIRGIGHLCKMWAERGCEHF
VCSSAGNAGMAAAYAARKLGIPSTIVVPSTTPALTIQRLKNEGATVKVVGETLDEAIRVA
KDLEKNNSGWVYVPPFDDPLIWEGHSSIVKELKETMTEKPGAIVLAVGGGGLLCGVVQGL
AEVGWRDVPVITMETIGAESFHASTKAGKLVTLPCITSVAKALGVTTVAAQAMKVYREHP
IFSEVVSDQEAVAALEKFVDDEKILVEPACGAALAAVYSNVIQKLQGEGKLRTPLSSLVV
IVCGGSNISLAQLVALKKQLGMDGLSQ
Enzyme 1 Number of Residues 327
Enzyme 1 Molecular Weight 34440.8
Enzyme 1 Theoretical pI 7.44
Enzyme 1 GO Classification
Function
Process
Component
Enzyme 1 General Function Amino acid transport and metabolism
Enzyme 1 Specific Function L-serine = pyruvate + NH(3)
Enzyme 1 Pathways
  • Carbohydrate biosynthesis
  • gluconeogenesis
Enzyme 1 Reactions Not Available
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 111307504 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q0VCW4 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name SDHL_BOVIN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >984 bp
ATGATGTCAGGAAGACCCTTGCACATGGAAACTCCGGTCCGTGACAGCATGACTCTGTCT
AAAGTGGCTGGCACCACGGCCTATCTCAAGCTAGACAGTGCCCAGCCCTCCGGCTCCTTC
AAGATCCGGGGCATCGGACACCTCTGCAAAATGTGGGCCGAGCGGGGCTGCGAGCATTTC
GTCTGCTCCTCAGCGGGCAATGCAGGCATGGCAGCCGCCTATGCTGCCAGGAAGCTGGGC
ATCCCCTCCACGATTGTCGTGCCCAGCACCACGCCTGCCCTCACCATCCAGCGGCTCAAG
AATGAGGGCGCCACGGTCAAAGTGGTGGGTGAGACATTGGATGAGGCCATCAGAGTGGCC
AAGGACCTGGAGAAAAACAACTCAGGCTGGGTCTATGTCCCCCCCTTTGACGACCCCCTC
ATCTGGGAAGGCCACTCTTCCATCGTGAAGGAGCTGAAGGAGACGATGACCGAAAAGCCA
GGGGCCATCGTGCTGGCAGTAGGGGGCGGAGGCCTCTTGTGCGGAGTGGTTCAGGGGCTG
GCAGAGGTGGGCTGGAGGGACGTGCCCGTCATCACCATGGAGACCATCGGAGCAGAGAGC
TTCCACGCTTCCACCAAGGCCGGCAAGCTCGTCACCCTGCCCTGCATTACCAGTGTTGCC
AAAGCCCTGGGCGTGACCACCGTGGCAGCGCAGGCTATGAAGGTTTATCGGGAACATCCC
ATTTTCTCTGAAGTTGTCTCGGACCAGGAAGCTGTGGCCGCTCTTGAGAAGTTTGTGGAT
GATGAGAAGATCCTGGTGGAGCCCGCCTGTGGGGCCGCCCTGGCCGCCGTCTACAGCAAC
GTGATTCAGAAGCTGCAAGGAGAGGGGAAACTCCGCACCCCGCTGTCCTCCCTCGTGGTC
ATTGTTTGTGGGGGCAGCAACATCAGCCTGGCGCAGCTGGTGGCGCTCAAGAAGCAGCTG
GGCATGGACGGGCTGTCCCAGTGA
Enzyme 1 GenBank Gene ID BC119966 Link Image
Enzyme 1 GeneCard ID SDS Link Image
Enzyme 1 GenAtlas ID Not Available
Enzyme 1 HGNC ID Not Available
Enzyme 1 Chromosome Location Chromosome:1
Enzyme 1 Locus 12q24.13
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References Not Available
Enzyme 1 Metabolite References Not Available
Enzyme 2 [top]
Enzyme 2 ID 818
Enzyme 2 Name Cystathionine gamma-lyase
Enzyme 2 Synonyms
  1. Gamma-cystathionase
Enzyme 2 Gene Name CTH
Enzyme 2 Protein Sequence >Cystathionine gamma-lyase
MQEKEASPHGFLPRFQHFATQAIHVGQEPEQWTSQAVVPPISLSTTFKQGAPGQHSGFEY
SRSGNPTRNCLEKAVAALDGAKYSLAFASGLAATVTITHLLKAGDQIICMDDVYGGTNRY
FRQVATEFGLKISFVDCSKPKLLEAAITPETKLVWIETPTNPSLKMIDIEACAHTVHKHG
DIILVVDNTFMSAYFQRPLSLGADICMYSATKYMNGYSDVVMGLVSLNSESLHDRLRFLQ
NSLGAVPSPIDCYLCNRGLKTLQVRMEKHFENGMAVAQFLESNPQVEKVIYPGLPSHPQH
ELAKRQCTGCPGMVTFYIKGSLQHAETFLQNLKLFTLAESLGGYESLAELPAIMTHASVP
KSDREVLGISDTLIRLSVGLEDKQDLLDDLDQALKAANPPNASSN
Enzyme 2 Number of Residues 405
Enzyme 2 Molecular Weight 44405.3
Enzyme 2 Theoretical pI 6.39
Enzyme 2 GO Classification
Function
Process
Component
Enzyme 2 General Function Amino acid transport and metabolism
Enzyme 2 Specific Function L-cystathionine + H(2)O = L-cysteine + NH(3) + 2-oxobutanoate
Enzyme 2 Pathways
  • Amino-acid biosynthesis
  • L-cysteine biosynthesis
  • L- cysteine from L-homocysteine and L-serine:step 2/2
Enzyme 2 Reactions Not Available
Enzyme 2 Pfam Domain Function
Enzyme 2 Signals
  • None
Enzyme 2 Transmembrane Regions
  • None
Enzyme 2 Essentiality Not Available
Enzyme 2 GenBank ID Protein 61552994 Link Image
Enzyme 2 UniProtKB/Swiss-Prot ID Q58DW2 Link Image
Enzyme 2 UniProtKB/Swiss-Prot Entry Name CGL_BOVIN Link Image
Enzyme 2 PDB ID Not Available
Enzyme 2 Cellular Location Not Available
Enzyme 2 Gene Sequence >1218 bp
ATGCAGGAAAAAGAAGCCTCCCCACACGGATTCCTGCCTAGGTTCCAGCATTTCGCTACG
CAGGCCATCCACGTGGGCCAAGAACCGGAGCAATGGACCTCCCAAGCTGTAGTGCCCCCT
ATCTCGCTGTCCACCACGTTCAAGCAAGGGGCTCCTGGCCAGCACTCGGGTTTTGAGTAT
AGCCGTTCTGGAAATCCCACCCGGAATTGCTTGGAAAAAGCAGTGGCGGCGCTGGATGGG
GCTAAGTACAGTTTGGCCTTTGCTTCAGGTTTAGCAGCCACTGTGACCATTACCCATCTC
TTAAAAGCAGGAGACCAGATTATTTGTATGGATGATGTGTATGGAGGTACAAACAGGTAC
TTCAGGCAGGTGGCAACTGAATTTGGATTAAAGATTTCTTTTGTTGATTGTTCCAAACCC
AAATTGCTAGAGGCAGCTATTACACCAGAAACCAAGCTTGTTTGGATTGAAACCCCCACA
AACCCTAGCTTGAAGATGATTGACATTGAAGCCTGCGCACATACGGTCCATAAACATGGA
GACATCATTTTGGTTGTGGATAACACTTTTATGTCAGCATATTTCCAGCGGCCTTTGTCT
CTGGGAGCTGATATTTGTATGTATTCAGCAACAAAATACATGAATGGCTACAGTGATGTT
GTAATGGGCTTAGTGTCACTGAATTCTGAGAGCCTTCATGATAGGCTCCGTTTCTTGCAA
AATTCTCTTGGAGCAGTTCCATCTCCTATTGACTGTTACCTCTGCAATCGGGGTCTGAAG
ACTCTACAAGTCCGCATGGAGAAGCATTTCGAAAACGGAATGGCAGTTGCTCAGTTTTTG
GAGTCGAATCCTCAGGTGGAAAAGGTTATTTATCCTGGGCTGCCTTCTCATCCTCAGCAT
GAGCTGGCCAAGCGTCAGTGCACAGGTTGCCCGGGGATGGTCACCTTTTATATCAAGGGC
TCTCTTCAACATGCTGAAACTTTCCTCCAGAACTTAAAGTTATTTACTCTGGCTGAAAGC
TTGGGAGGATACGAAAGTCTTGCTGAGCTTCCGGCAATCATGACCCATGCATCAGTGCCT
AAGAGTGACAGAGAAGTCCTTGGAATTAGTGACACACTTATTCGACTCTCAGTGGGCTTA
GAGGATAAACAAGACCTACTGGATGATCTAGATCAAGCTTTGAAGGCAGCTAACCCTCCA
AATGCAAGTTCCAACTAG
Enzyme 2 GenBank Gene ID BT021485 Link Image
Enzyme 2 GeneCard ID CTH Link Image
Enzyme 2 GenAtlas ID Not Available
Enzyme 2 HGNC ID Not Available
Enzyme 2 Chromosome Location Chromosome:1
Enzyme 2 Locus 1p31.1
Enzyme 2 SNPs SNPJam Report Link Image
Enzyme 2 General References
  1. [PubMed Link Image]
Enzyme 2 Metabolite References Not Available