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Identification
YMDB IDYMDB00250
NameS-adenosyl-4-methylthio-2-oxobutanoic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionS-Adenosyl-4-methylthio-2-oxobutanoate belongs to the class of organic compounds known as 5'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group. S-Adenosyl-4-methylthio-2-oxobutanoate is a strong basic compound (based on its pKa). S-Adenosyl-4-methylthio-2-oxobutanoate exists in both E. coli (prokaryote) and yeast (eukaryote).
Structure
Thumb
Synonyms
  • (3-carboxy-3-oxopropyl)(5'-deoxyadenosin-5'-yl)(methyl)sulfonium
  • [1-(adenin-9-yl)-1,5-dideoxy-beta-D-ribofuranos-5-yl][(3S)-3-carboxylato-3-oxopropyl](methyl)sulfonium
  • {[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}(3-carboxy-3-oxopropyl)methylsulfonium
  • 4-[(5'-adenosyl)(methyl)sulfonio]-2-oxobutanoate
  • 4-[(5'-deoxyadenosin-5'-yl)(methyl)sulfonio]-2-oxobutanoate
  • 4-[{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}(methyl)sulfonio]-2-oxobutanoate
  • S-Adenosyl-4-methylthio-2-oxobutanoate
  • S-Adenosyl-4-(methylsulfanyl)-2-oxobutanoate
  • (3-Carboxy-3-oxopropyl)(5'-deoxyadenosin-5'-yl)(methyl)sulphonium
  • {[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}(3-carboxy-3-oxopropyl)methylsulphonium
  • S-Adenosyl-4-(methylsulfanyl)-2-oxobutanoic acid
  • S-Adenosyl-4-(methylsulphanyl)-2-oxobutanoate
  • S-Adenosyl-4-(methylsulphanyl)-2-oxobutanoic acid
  • S-Adenosyl-4-methylthio-2-oxobutanoic acid
CAS numberNot Available
WeightAverage: 398.414
Monoisotopic: 398.113429087
InChI KeyUOKVQQMBGVMXPU-CJPDYEHRSA-O
InChIInChI=1S/C15H19N5O6S/c1-27(3-2-7(21)15(24)25)4-8-10(22)11(23)14(26-8)20-6-19-9-12(16)17-5-18-13(9)20/h5-6,8,10-11,14,22-23H,2-4H2,1H3,(H2-,16,17,18,24,25)/p+1/t8-,10-,11-,14-,27?/m1/s1
IUPAC Name{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(3-carboxy-3-oxopropyl)methylsulfanium
Traditional IUPAC Name{[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(3-carboxy-3-oxopropyl)methylsulfanium
Chemical FormulaC15H20N5O6S
SMILESC[S+](CCC(=O)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 5'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
Class5'-deoxyribonucleosides
Sub Class5'-deoxy-5'-thionucleosides
Direct Parent5'-deoxy-5'-thionucleosides
Alternative Parents
Substituents
  • 5'-deoxy-5'-thionucleoside
  • N-glycosyl compound
  • Glycosyl compound
  • Pentose monosaccharide
  • 6-aminopurine
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Hydroxy fatty acid
  • Thia fatty acid
  • Alpha-keto acid
  • N-substituted imidazole
  • Keto acid
  • Fatty acyl
  • Monosaccharide
  • Imidolactam
  • Pyrimidine
  • Alpha-hydroxy ketone
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Tetrahydrofuran
  • Amino acid
  • Ketone
  • 1,2-diol
  • Amino acid or derivatives
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge1
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.98 g/LALOGPS
logP-0.25ALOGPS
logP-3.6ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)2.75ChemAxon
pKa (Strongest Basic)4.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area173.68 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity93.72 m³·mol⁻¹ChemAxon
Polarizability38.63 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Biotin BiosynthesisPW002380 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
8-Amino-7-oxononanoic acid + S-AdenosylmethionineS-adenosyl-4-methylthio-2-oxobutanoic acid + 7,8-diaminononanoic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0904000000-1854da0ef2f564469fbfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-facbde7ab625c6a72b7aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900000000-6e11c0cb1f77f010c2c9JSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID8944
HMDB IDNot Available
Pubchem Compound ID440336
Kegg IDC04425
ChemSpider ID24785122
FOODB IDFDB031149
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in transaminase activity
Specific function:
Catalyzes the transfer of the alpha-amino group from S- adenosyl-L-methionine (SAM) to 7-keto-8-aminopelargonic acid (KAPA) to form 7,8-diaminopelargonic acid (DAPA). It is the only animotransferase known to utilize SAM as an amino donor
Gene Name:
BIO3
Uniprot ID:
P50277
Molecular weight:
53708.39844
Reactions
S-adenosyl-L-methionine + 8-amino-7-oxononanoate → S-adenosyl-4-methylthio-2-oxobutanoate + 7,8-diaminononanoate.