Details of the Drug

General Information of Drug (ID: DMC8J6F)

Drug Name
METHYLTHIOADENOSINE
Synonyms
5'-Deoxy-5'-methylthioadenosine; 2457-80-9; Methylthioadenosine; 5'-S-methyl-5'-thioadenosine; 5'-Deoxy-5'-(methylthio)adenosine; 5'-DEOXY-5'-METHYLTHIOADENOSINE; (2R,3R,4S,5S)-2-(6-Amino-9H-purin-9-yl)-5-((methylthio)methyl)tetrahydrofuran-3,4-diol; Thiomethyladenosine; Vitamin L2; ADENOSINE, 5'-S-METHYL-5'-THIO-; 5'-S-Methylthioadenosine; MTA; S-methyl-5'-thioadenosine; Vitamin L(sub 2); UNII-634Z2VK3UQ; 5'-Deoxy(methylthio)adenosine; 5'-Deoxy-5'-Methylthioadenosine
Indication
Disease Entry ICD 11 Status REF
Multiple sclerosis 8A40 Terminated [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 297.34
Logarithm of the Partition Coefficient (xlogp) -0.3
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 8
Chemical Identifiers
Formula
C11H15N5O3S
IUPAC Name
(2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-(methylsulfanylmethyl)oxolane-3,4-diol
Canonical SMILES
CSC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)O
InChI
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
Cross-matching ID
PubChem CID
439176
ChEBI ID
CHEBI:17509
CAS Number
2457-80-9
UNII
634Z2VK3UQ
DrugBank ID
DB02282
TTD ID
D0E4WF
INTEDE ID
DR2066

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Adenosine A1 receptor (ADORA1) TTK25J1 AA1R_HUMAN Inhibitor [2]
Adenosine A2a receptor (ADORA2A) TTM2AOE AA2AR_HUMAN Inhibitor [2]
Adenosine A2b receptor (ADORA2B) TTNE7KG AA2BR_HUMAN Inhibitor [2]
Adenosine A3 receptor (ADORA3) TTJFY5U AA3R_HUMAN Inhibitor [2]
S-methyl-5'-thioadenosine phosphorylase (MTAP) TTDBX7N MTAP_HUMAN Inhibitor [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
S-adenosylhomocysteine nucleosidase (mtnN) DE1DR6Y MTNN_KLEPN Substrate [4]
S-methyl-5'-thioadenosine phosphorylase (MTAP) DEXHBCR MTAP_HUMAN Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cellular tumor antigen p53 (TP53) OTIE1VH3 P53_HUMAN Gene/Protein Processing [6]
Collagen alpha-1(I) chain (COL1A1) OTI31178 CO1A1_HUMAN Gene/Protein Processing [7]
Collagen alpha-2(I) chain (COL1A2) OTY7G382 CO1A2_HUMAN Gene/Protein Processing [7]
Interferon gamma (IFNG) OTXG9JM7 IFNG_HUMAN Protein Interaction/Cellular Processes [6]
Interleukin-2 (IL2) OTGI4NSA IL2_HUMAN Protein Interaction/Cellular Processes [6]
RAC-alpha serine/threonine-protein kinase (AKT1) OT8H2YY7 AKT1_HUMAN Post-Translational Modifications [6]
Serine/threonine-protein kinase mTOR (MTOR) OTHH8KU7 MTOR_HUMAN Post-Translational Modifications [6]
Small ribosomal subunit protein eS6 (RPS6) OTT4D1LN RS6_HUMAN Post-Translational Modifications [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

ICD Disease Classification 08 Nervous system disease
Disease Class ICD-11: 8A40 Multiple sclerosis
The Studied Tissue Plasmacytoid dendritic cells
The Studied Disease Multiple sclerosis [ICD-11:8A40]
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
S-methyl-5'-thioadenosine phosphorylase (MTAP) DME MTAP 2.81E-01 -6.84E-02 -2.78E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

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 Novel amino acid derived natural products from the ascidian Atriolum robustum: identification and pharmacological characterization of a unique aden... J Med Chem. 2004 Apr 22;47(9):2243-55.
3 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
4 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.
5 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.
6 Selective PRMT5 Inhibitors Suppress Human CD8(+) T Cells by Upregulation of p53 and Impairment of the AKT Pathway Similar to the Tumor Metabolite MTA. Mol Cancer Ther. 2020 Feb;19(2):409-419. doi: 10.1158/1535-7163.MCT-19-0189. Epub 2019 Nov 11.
7 S-adenosylmethionine blocks collagen I production by preventing transforming growth factor-beta induction of the COL1A2 promoter. J Biol Chem. 2005 Sep 2;280(35):30963-74. doi: 10.1074/jbc.M503569200. Epub 2005 Jun 27.