Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR2066)
Drug Name
Methylthioadenosine
Synonyms
S-methyl-5'-thioadenosine; Thiomethyladenosine; 5'-Methylthioadenosine; ADENOSINE, 5'-S-METHYL-5'-THIO-; Vitamin L(sub 2); Vitamin L2; (2R,3R,4S,5S)-2-(6-Amino-9H-purin-9-yl)-5-((methylthio)methyl)tetrahydrofuran-3,4-diol; 2457-80-9; 5'-(Methylthio)-5'-deoxyadenosine; 5'-(Methylthio)adenosine; 5'-DEOXY-5'-METHYLTHIOADENOSINE; 5'-Deoxy(methylthio)adenosine; 5'-Deoxy-5'-(methylthio)adenosine; 5'-S-Methylthioadenosine; 5'-S-methyl-5'-thioadenosine; 5'-methylthioadenosine; 5-Methylthioadenosine; MTA; NSC 335422; UNII-634Z2VK3UQ
Indication Multiple sclerosis [ICD11: 8A40] Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 297.34 Topological Polar Surface Area 145
Heavy Atom Count 20 Rotatable Bond Count 3
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
439176
ChEBI ID
CHEBI:17509
CAS Number
2457-80-9
TTD Drug ID
D0E4WF
Formula
C11H15N5O3S
Canonical SMILES
CSCC1C(C(C(O1)N2C=NC3=C2N=CN=C3N)O)O
InChI
1S/C11H15N5O3S/c1-20-2-5-7(17)8(18)11(19-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1
InChIKey
WUUGFSXJNOTRMR-IOSLPCCCSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Adenine DM003899
190
Unclear 1 [2]
MTR-1-P DM003900
11988266
Unclear 1 [2]
Adenosine Phosphate DM000018
6083
Unclear 2 [2]
Methionine DM003070
6992087
Unclear 2 [2]
ATP DM000020
5957
Unclear 3 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004264 Methylthioadenosine Adenine Unclear MTAP [2]
MR004267 Methylthioadenosine MTR-1-P Unclear MTAP [2]
MR004265 Adenine AMP Unclear APRT [2]
MR004268 MTR-1-P Methionine Unclear Unclear [2]
MR004266 AMP ATP Unclear Unclear [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Adenine phosphoribosyltransferase (APRT) DME0078 Homo sapiens
APT_HUMAN
2.4.2.7
[2]
S-adenosylhomocysteine nucleosidase (mtnN) DME1115 Klebsiella pneumoniae
MTNN_KLEPN
3.2.2.9
[3]
S-methyl-5'-thioadenosine phosphorylase (MTAP) DME0464 Homo sapiens
MTAP_HUMAN
2.4.2.28
[4]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
S-methyl-5'-thioadenosine phosphorylase (MTAP) DME0464 Km = 0.005 microM
MTAP_HUMAN
[4]
References
1 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800000987)
2 Targeting tumors that lack methylthioadenosine phosphorylase (MTAP) activity: current strategies
3 Selective killing of Klebsiella pneumoniae by 5-trifluoromethylthioribose. Chemotherapeutic exploitation of the enzyme 5-methylthioribose kinase. J Biol Chem. 1990 Jan 15;265(2):831-7.
4 Picomolar transition state analogue inhibitors of human 5'-methylthioadenosine phosphorylase and X-ray structure with MT-immucillin-A. Biochemistry. 2004 Jan 13;43(1):9-18.

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