4-amino-5-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methylsulfanylmethyl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one

ID: ALA5189315

PubChem CID: 66718251

Max Phase: Preclinical

Molecular Formula: C20H26N8O7S

Molecular Weight: 522.54

Names and Identifiers

Canonical SMILES:  Nc1nc(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C20H26N8O7S/c21-16-8(2-27(20(33)26-16)12-1-9(30)10(3-29)34-12)4-36-5-11-14(31)15(32)19(35-11)28-7-25-13-17(22)23-6-24-18(13)28/h2,6-7,9-12,14-15,19,29-32H,1,3-5H2,(H2,21,26,33)(H2,22,23,24)/t9-,10+,11+,12+,14+,15+,19+/m0/s1

Standard InChI Key:  RDGKDEZKZNBISB-SLFMBYJQSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA5189315

   4-amino-5-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methylsulfanylmethyl]-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 522.54

Molecular Weight (Monoisotopic): 522.1645

AlogP: -2.26

#Rotatable Bonds: 7

Polar Surface Area: 229.91

Molecular Species: NEUTRAL

HBA: 16

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 15

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.46

CX Basic pKa: 4.92

CX LogP: -2.98

CX LogD: -2.98

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.19

Np Likeness Score: 0.72

References

1. Lamiable-Oulaidi F, Harijan RK, Shaffer KJ, Crump DR, Sun Y, Du Q, Gulab SA, Khan AA, Luxenburger A, Woolhouse AD, Sidoli S, Tyler PC, Schramm VL..  (2022)  Synthesis and Characterization of Transition-State Analogue Inhibitors against Human DNA Methyltransferase 1.,  65  (7.0): [PMID:35324190] [10.1021/acs.jmedchem.1c01869]

Source

Source(1):

• Scientific Literature