2-amino-9-[(2R,3R,4S,5R)-5-{[({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}(sulfanidyl)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-7-methyl-6-oxido-9H-purin-7-ium

ID: ALA3351002

Max Phase: Preclinical

Molecular Formula: C21H29N10O17P3S

Molecular Weight: 818.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[n+]1cn([C@@H]2O[C@H](CO[P@](=O)(S)OP(=O)([O-])OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(=O)[nH]c(N)nc54)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)c2nc(N)nc(O)c21

Standard InChI:  InChI=1S/C21H29N10O17P3S/c1-29-5-31(15-9(29)17(37)28-21(23)26-15)19-13(35)11(33)7(46-19)3-44-51(42,52)48-50(40,41)47-49(38,39)43-2-6-10(32)12(34)18(45-6)30-4-24-8-14(30)25-20(22)27-16(8)36/h4-7,10-13,18-19,32-35H,2-3H2,1H3,(H8-,22,23,25,26,27,28,36,37,38,39,40,41,42,52)/t6-,7-,10-,11-,12-,13-,18-,19-,51+/m1/s1

Standard InChI Key:  ZOGKCMJMDRGRLC-MDWXPYCMSA-N

Molfile:  

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M  CHG  2  34   1  46  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3351002

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 818.51

Molecular Weight (Monoisotopic): 818.0646

AlogP: -3.83

#Rotatable Bonds: 12

Polar Surface Area: 401.23

Molecular Species: ACID

HBA: 24

HBD: 10

#RO5 Violations: 3

HBA (Lipinski): 27

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.66

CX Basic pKa: 2.14

CX LogP: -9.08

CX LogD: -12.74

Aromatic Rings: 4

Heavy Atoms: 52

QED Weighted: 0.04

Np Likeness Score: 0.70

References

1. Kowalska J, Lukaszewicz M, Zuberek J, Ziemniak M, Darzynkiewicz E, Jemielity J..  (2009)  Phosphorothioate analogs of m7GTP are enzymatically stable inhibitors of cap-dependent translation.,  19  (7): [PMID:19269171] [10.1016/j.bmcl.2009.02.053]

Source

Source(1):

• Scientific Literature