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Human Metabolome Database Version 2.5

 

Showing metabocard for 2-Oxo-4-methylthiobutanoic acid (HMDB01553)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2005-11-16 15:48:42
Update Date 2009-12-08 11:12:00
Accession Number HMDB01553
Secondary Accession Numbers HMDB13210
Common Name 2-Oxo-4-methylthiobutanoic acid
Description 4-Methylthio-2-oxobutanoic acid is the direct precursor of methional, which is a potent inducer of apoptosis in a BAF3 murine lymphoid cell line which is interleukin-3 (IL3)-dependent. (PMID 7848263)
Synonyms
  1. 2-Oxo-4-methylthiobutanoate
  2. 2-keto-4-methylthiobutyrate
  3. 2-keto-4-methylthiobutyric acid
  4. 2-ketomethiobutyrate
  5. 2-oxo-4-methylthiobutanoic acid
  6. 4-methylthio-2-ketobutanoate
  7. 4-methylthio-2-ketobutyrate
  8. 4-methylthio-2-oxobutanoate
  9. 4-methylthio-2-oxobutanoic acid
  10. 4-methylthio-2-oxobutyrate
  11. KMTB
  12. keto-4-methylthiobutyrate
  13. ketomethiobutyrate
  14. ketomethiobutyric acid
  15. methylthiobutyrate
  16. methylthiobutyric acid
  17. 4-methylthio-2-ketobutanoic acid;alpha-Keto-methiolbutyric acid
Chemical IUPAC Name 4-methylsulfanyl-2-oxo-butanoic acid
Chemical Formula C5H8O3S
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Keto-Acids
Sub Class
  • Sulfur-containing keto-acids
Family
  • Mammalian Metabolite
Species
  • ketone
  • thioether
  • carboxylic acid
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 148.180
Monoisotopic Molecular Weight 148.019409
Isomeric SMILES CSCCC(=O)C(O)=O
Canonical SMILES CSCCC(=O)C(O)=O
KEGG Compound ID C01180 Link Image
BioCyc ID CPD-479 Link Image
BiGG ID 228408 Link Image
Wikipedia Link Not Available
NuGOwiki Link HMDB01553 Link Image
Metagene Link HMDB01553 Link Image
METLIN ID 6319 Link Image
PubChem Compound 473 Link Image
PubChem Substance 5057160 Link Image
ChEBI ID 16723 Link Image
CAS Registry Number 583-92-6
InChI Identifier InChI=1/C5H8O3S/c1-9-3-2-4(6)5(7)8/h2-3H2,1H3,(H,7,8)
Synthesis Reference Brodelius, P.; Hagerdal, B.; Mosbach, K. Immobilized whole cells of the yeast Trigonopsis variabilis containing D-amino acid oxidase for the production of a-keto acids. Enzyme Engineering (1980), 5 383-7.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 7.44 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]; 0.4 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
Biofluid Location
  • Urine
Tissue Location Not Available
Concentrations (Normal)
Biofluid Urine
Value 0.02 umol/mmol creatinine
Age Children:1-13 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Methionine Metabolism SMP00033 Link Image map00270 Link Image
General References
  1. Martensson J: The occurrence of 4-methylthio-2-hydroxybutyrate in human urine. Anal Biochem. 1986 Apr;154(1):43-9. [PubMed Link Image]
Metabolic Enzymes
  1. Tyrosine aminotransferase
  2. cDNA, FLJ93913, Homo sapiens tyrosine aminotransferase (TAT), nuclear gene encodingmitochondrial protein, mRNA (Tyrosine aminotransferase, isoform CRA_a)
Enzyme 1 [top]
Enzyme 1 ID 5509
Enzyme 1 Name Tyrosine aminotransferase
Enzyme 1 Synonyms
  1. L-tyrosine:2-oxoglutarate aminotransferase
  2. TAT
Enzyme 1 Gene Name TAT
Enzyme 1 Protein Sequence >Tyrosine aminotransferase 
MDPYMIQMSSKGNLPSILDVHVNVGGRSSVPGKMKGRKARWSVRPSDMAKKTFNPIRAIV
DNMKVKPNPNKTMISLSIGDPTVFGNLPTDPEVTQAMKDALDSGKYNGYAPSIGFLSSRE
EIASYYHCPEAPLEAKDVILTSGCSQAIDLCLAVLANPGQNILVPRPGFSLYKTLAESMG
IEVKLYNLLPEKSWEIDLKQLEYLIDEKTACLIVNNPSNPCGSVFSKRHLQKILAVAARQ
CVPILADEIYGDMVFSDCKYEPLATLSTDVPILSCGGLAKRWLVPGWRLGWILIHDRRDI
FGNEIRDGLVKLSQRILGPCTIVQGALKSILCRTPGEFYHNTLSFLKSNADLCYGALAAI
PGLRPVRPSGAMYLMVGIEMEHFPEFENDVEFTERLVAEQSVHCLPATCFEYPNFIRVVI
TVPEVMMLEACSRIQEFCEQHYHCAEGSQEECDK
Enzyme 1 Number of Residues 454
Enzyme 1 Molecular Weight 50400
Enzyme 1 Theoretical pI 6.24
Enzyme 1 GO Classification
Function
  • 1-aminocyclopropane-1-carboxylate synthase activity
  • binding
  • carbon-sulfur lyase activity
  • catalytic activity
  • lyase activity
  • pyridoxal phosphate binding
  • transaminase activity
  • transferase activity
  • transferase activity, transferring nitrogenous groups
  • tyrosine transaminase activity
  • vitamin binding
Process
  • amino acid and derivative metabolism
  • amino acid catabolism
  • amino acid metabolism
  • aromatic amino acid family catabolism
  • aromatic amino acid family metabolism
  • biosynthesis
  • cellular metabolism
  • metabolism
  • physiological process
Component
—
Enzyme 1 General Function Amino acid transport and metabolism
Enzyme 1 Specific Function L-tyrosine + 2-oxoglutarate = 4- hydroxyphenylpyruvate + L-glutamate
Enzyme 1 Pathways
Enzyme 1 Reactions
  • L-tyrosine + 2-oxoglutarate = 4-hydroxyphenylpyruvate + L-glutamate
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 36713 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID P17735 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name ATTY_HUMAN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >1365 bp 
ATGGACCCATACATGATTCAGATGAGCAGCAAAGGCAACCTCCCCTCAATTCTGGACGTG
CATGTCAACGTTGGTGGGAGAAGCTCTGTGCCGGGAAAAATGAAAGGCAGAAAGGCCAGG
TGGTCTGTGAGGCCCTCAGACATGGCCAAGAAAACTTTCAACCCCATCCGAGCCATTGTG
GACAACATGAAGGTGAAACCAAATCCAAACAAAACCATGATTTCCCTGTCCATTGGGGAC
CCTACTGTGTTTGGAAACCTGCCTACAGACCCTGAAGTTACCCAGGCAATGAAAGATGCC
CTGGACTCGGGCAAATATAATGGCTATGCCCCATCCATCGGCTTCCTATCCAGTCGGGAG
GAGATTGCTTCTTATTACCACTGTCCTGAGGCACCCCTAGAAGCTAAGGACGTCATTCTG
ACAAGTGGCTGCAGCCAAGCTATTGACCTTTGTTTAGCTGTGTTGGCCAACCCAGGGCAG
AACATCCTGGTTCCAAGACCTGGTTTCTCTCTCTACAAGACTCTGGCTGAGTCTATGGGA
ATTGAGGTCAAACTCTACAATTTGTTGCCAGAGAAATCTTGGGAAATTGACCTGAAACAA
CTGGAATATCTAATTGATGAAAAGACAGCTTGTCTCATTGTCAATAATCCATCAAACCCC
TGTGGGTCAGTGTTCAGCAAACGTCATCTTCAGAAGATTCTGGCAGTGGCTGCACGGCAG
TGTGTCCCCATCTTAGCTGATGAGATCTATGGAGACATGGTGTTTTCGGATTGCAAATAT
GAACCACTGGCCACCCTCAGCACCGATGTCCCCATCCTGTCCTGTGGAGGGCTGGCCAAG
CGCTGGCTGGTTCCTGGCTGGAGGTTGGGCTGGATCCTCATTCATGACCGAAGAGACATT
TTTGGCAATGAGATCCGAGATGGGCTGGTGAAGCTGAGTCAGCGCATTTTGGGACCCTGT
ACCATTGTCCAGGGAGCTCTGAAAAGCATCCTATGTCGCACCCCGGGAGAGTTTTACCAC
AACACTCTGAGCTTCCTCAAGTCCAATGCTGATCTCTGTTATGGGGCGTTGGCTGCCATC
CCTGGACTCCGGCCAGTCCGCCCTTCTGGGGCTATGTACCTCATGGTTGGAATTGAGATG
GAACATTTCCCAGAATTTGAGAACGATGTGGAGTTCACGGAGCGGTTAGTTGCTGAGCAG
TCTGTCCACTGCCTCCCAGCAACGTGCTTTGAGTACCCGAATTTCATCCGAGTGGTCATC
ACAGTCCCCGAGGTGATGATGCTGGAGGCGTGCAGCCGGATCCAGGAGTTCTGTGAGCAG
CACTACCATTGTGCTGAAGGCAGCCAGGAGGAGTGTGATAAATAG
Enzyme 1 GenBank Gene ID X52520 Link Image
Enzyme 1 GeneCard ID TAT Link Image
Enzyme 1 GenAtlas ID TAT Link Image
Enzyme 1 HGNC ID HGNC:11573 Link Image
Enzyme 1 Chromosome Location 16
Enzyme 1 Locus 16q22.1
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. Rettenmeier R, Natt E, Zentgraf H, Scherer G: Isolation and characterization of the human tyrosine aminotransferase gene. Nucleic Acids Res. 1990 Jul 11;18(13):3853-61. [PubMed Link Image]
  2. Zelenin SM, Mertvetsov NP: [Nucleotide sequence of the human tyrosine aminotransferase gene] Bioorg Khim. 1994 Feb;20(2):196-204. [PubMed Link Image]
  3. Seralini GE, Luu-The V, Labrie F: Cloning and expression of human tyrosine aminotransferase cDNA. Biochim Biophys Acta. 1995 Jan 2;1260(1):97-101. [PubMed Link Image]
  4. Natt E, Kida K, Odievre M, Di Rocco M, Scherer G: Point mutations in the tyrosine aminotransferase gene in tyrosinemia type II. Proc Natl Acad Sci U S A. 1992 Oct 1;89(19):9297-301. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available
Enzyme 2 [top]
Enzyme 2 ID 16503
Enzyme 2 Name cDNA, FLJ93913, Homo sapiens tyrosine aminotransferase (TAT), nuclear gene encodingmitochondrial protein, mRNA (Tyrosine aminotransferase, isoform CRA_a)
Enzyme 2 Synonyms Not Available
Enzyme 2 Gene Name TAT
Enzyme 2 Protein Sequence >cDNA, FLJ93913, Homo sapiens tyrosine aminotransferase (TAT), nuclear gene encodingmitochondrial protein, mRNA (Tyrosine aminotransferase, isoform CRA_a) 
MDPYMIQMSSKGNLPSILDVHVNVGGRSSVPGKMKGRKARWSVRPSDMAKKTFNPIRAIV
DNMKVKPNPNKTMISLSIGDPTVFGNLPTDPEVTQAMKDALDSGKYNGYAPSIGFLSSRE
EIASYYHCPEAPLEAKDVILTSGCSQAIDLCLAVLANPGQNILVPRPGFSLYKTLAESMG
IEVKLYNLLPEKSWEIDLKQLEYLIDEKTACLIVNNPSNPCGSVFSKRHLQKILAVAARQ
CVPILADEIYGDMVFSDCKYEPLATLSTDVPILSCGGLAKRWLVPGWRLGWILIHDRRDI
FGNEIRDGLVKLSQRILGPCTIVQGALKSILCRTPGEFYHNTLSFLKSNADLCYGALAAI
PGLRPVRPSGAMYLMVGIEMEHFPEFENDVEFTERLVAEQSVHCLPATCFEYPNFIRVVI
TVPEVMMLEACSRIQEFCEQHYHCAEGSQEECDK
Enzyme 2 Number of Residues 454
Enzyme 2 Molecular Weight 50400
Enzyme 2 Theoretical pI 6.24
Enzyme 2 GO Classification
Function
  • 1-aminocyclopropane-1-carboxylate synthase activity
  • binding
  • carbon-sulfur lyase activity
  • catalytic activity
  • lyase activity
  • pyridoxal phosphate binding
  • transaminase activity
  • transferase activity
  • transferase activity, transferring nitrogenous groups
  • tyrosine transaminase activity
  • vitamin binding
Process
  • amino acid and derivative metabolism
  • amino acid catabolism
  • amino acid metabolism
  • aromatic amino acid family catabolism
  • aromatic amino acid family metabolism
  • biosynthesis
  • cellular metabolism
  • metabolism
  • physiological process
Component
—
Enzyme 2 General Function Amino acid transport and metabolism
Enzyme 2 Specific Function Not Available
Enzyme 2 Pathways Not Available
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 Not Available
Enzyme 2 UniProtKB/Swiss-Prot ID B2R8I1 Link Image
Enzyme 2 UniProtKB/Swiss-Prot Entry Name B2R8I1_HUMAN Link Image
Enzyme 2 PDB ID Not Available
Enzyme 2 Cellular Location Not Available
Enzyme 2 Gene Sequence Not Available
Enzyme 2 GenBank Gene ID AK313380 Link Image
Enzyme 2 GeneCard ID B2R8I1 Link Image
Enzyme 2 GenAtlas ID Not Available
Enzyme 2 HGNC ID Not Available
Enzyme 2 Chromosome Location 16
Enzyme 2 Locus 16q22.1
Enzyme 2 SNPs SNPJam Report Link Image
Enzyme 2 General References Not Available
Enzyme 2 Metabolite References Not Available