Methylthioadenosine

ID: ALA4877019

PubChem CID: 21120120

Max Phase: Preclinical

Molecular Formula: C11H15N5O4S

Molecular Weight: 313.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CS[C@@]1(n2cnc3c(N)ncnc32)O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C11H15N5O4S/c1-21-11(8(19)7(18)5(2-17)20-11)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,17-19H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11+/m1/s1

Standard InChI Key:  XTIFMHMNJQRXDW-FCKMSMMTSA-N

Molfile:  

 
     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   19.5417   -3.6501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9584   -4.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7588   -4.4489    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.8791   -5.0251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7042   -5.0251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2917   -3.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6267   -4.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3933   -5.6919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1883   -5.6931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1462   -2.4497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4099   -2.8283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9752   -5.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8419   -3.9863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6700   -3.1794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7338   -3.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3613   -3.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8124   -4.4575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6357   -4.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0060   -3.6704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5527   -2.9851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9219   -2.2473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  3  2  1  0
  4  5  1  0
  5  2  1  0
  2  6  1  0
  6  7  1  0
  7  4  1  0
  4  8  1  6
  5  9  1  6
  1 16  1  0
 15 10  1  0
 10 11  2  0
 11  1  1  0
  3 12  1  0
  7 13  1  1
 13 14  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4877019

   Methylthioadenosin

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 313.34

Molecular Weight (Monoisotopic): 313.0845

AlogP: -1.51

#Rotatable Bonds: 3

Polar Surface Area: 139.54

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.08

CX Basic pKa: 4.83

CX LogP: -1.04

CX LogD: -1.04

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.53

Np Likeness Score: 0.97

References

1. McKinney DC, McMillan BJ, Ranaghan MJ, Moroco JA, Brousseau M, Mullin-Bernstein Z, O'Keefe M, McCarren P, Mesleh MF, Mulvaney KM, Robinson F, Singh R, Bajrami B, Wagner FF, Hilgraf R, Drysdale MJ, Campbell AJ, Skepner A, Timm DE, Porter D, Kaushik VK, Sellers WR, Ianari A..  (2021)  Discovery of a First-in-Class Inhibitor of the PRMT5-Substrate Adaptor Interaction.,  64  (15.0): [PMID:34342224] [10.1021/acs.jmedchem.1c00507]

Source

Source(1):

• Scientific Literature