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S-adenosyl-4-methylthio-2-oxobutanoic acid (YMDB00250)

Identification
YMDB IDYMDB00250
NameS-adenosyl-4-methylthio-2-oxobutanoic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionS-adenosyl-4-methylthio-2-oxobutanoic acid, also known as S-adenosyl-4-(methylsulfanyl)-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. Based on a literature review a significant number of articles have been published on S-adenosyl-4-methylthio-2-oxobutanoic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
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-Adenosylmethionine ↔ S-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
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
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 IDHMDB0304475
Pubchem Compound ID440336
Kegg IDC04425
ChemSpider ID24785122
FOODB IDFDB031149
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Adenosylmethionine-8-amino-7-oxononanoate aminotransferase
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.