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S-Adenosyl-4-methylthio-2-oxobutanoate (M2MDB001688)

Record Information
Version2.0
Creation Date2012-07-30 14:55:12 -0600
Update Date2015-06-03 17:21:04 -0600
Secondary Accession Numbers
  • ECMDB21282
Identification
Name:S-Adenosyl-4-methylthio-2-oxobutanoate
DescriptionS-adenosyl-4-methylthio-2-oxobutanoate is a member of the chemical class known as Purine Nucleosides and Analogues. These are compounds comprising a purine base attached to a sugar.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (3-carboxy-3-oxopropyl)(5'-deoxyadenosin-5'-yl)(methyl)sulfanium
  • (3-carboxy-3-oxopropyl)(5'-deoxyadenosin-5'-yl)(methyl)sulfonium
  • (3-carboxy-3-oxopropyl)(5'-deoxyadenosin-5'-yl)(methyl)sulphanium
  • (3-carboxy-3-oxopropyl)(5'-deoxyadenosin-5'-yl)(methyl)sulphonium
  • S-Adenosyl-4-methylthio-2-oxobutanoate
  • S-Adenosyl-4-methylthio-2-oxobutanoic acid
  • SA4MT2OBA
  • {[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}(3-carboxy-3-oxopropyl)methylsulfonium
  • {[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}(3-carboxy-3-oxopropyl)methylsulphonium
Chemical Formula:C15H20N5O6S
Weight:Average: 398.414
Monoisotopic: 398.113429087
InChI Key:UOKVQQMBGVMXPU-CJPDYEHRSA-O
InChI:InChI=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
CAS number:Not Available
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
SMILES:C[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
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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
Reactions:
8-Amino-7-oxononanoate + S-Adenosylmethionine <> S-Adenosyl-4-methylthio-2-oxobutanoate + 7,8-Diaminononanoate
S-Adenosylmethionine + 8-Amino-7-oxononanoate > S-Adenosyl-4-methylthio-2-oxobutanoate + 7,8-Diaminononanoate
S-adenosyl-L-methionine + 8-Amino-7-oxononanoate > S-Adenosyl-4-methylthio-2-oxobutanoate + 7,8-Diaminononanoate
8 8-Amino-7-oxononanoate + S-Adenosylmethionine <> S-Adenosyl-4-methylthio-2-oxobutanoate +7 7,8-Diaminononanoate
8 8-Amino-7-oxononanoate + S-Adenosylmethionine <> S-Adenosyl-4-methylthio-2-oxobutanoate +7 7,8-Diaminononanoate
SMPDB Pathways:
Biotin metabolismPW000762 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
  • biotin biosynthesis from 7-keto-8-aminopelargonate PWY0-1507
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0904000000-1854da0ef2f564469fbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-facbde7ab625c6a72b7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900000000-6e11c0cb1f77f010c2c9View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID8944
HMDB IDHMDB0304475
Pubchem Compound ID440336
Kegg IDC04425
ChemSpider ID389303
Wikipedia IDNot Available
BioCyc IDS-ADENOSYL-4-METHYLTHIO-2-OXOBUTANOATE
EcoCyc IDS-ADENOSYL-4-METHYLTHIO-2-OXOBUTANOATE

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:
bioA
Uniprot ID:
P12995
Molecular weight:
47335
Reactions
S-adenosyl-L-methionine + 8-amino-7-oxononanoate = S-adenosyl-4-methylthio-2-oxobutanoate + 7,8-diaminononanoate.