ID: ALA590527

Max Phase: Preclinical

Molecular Formula: C12H20N5O12P3S

Molecular Weight: 551.30

Molecule Type: Small molecule

Representations

Canonical SMILES:  CSc1nc(N)c2ncn([C@@H]3O[C@H](COP(=O)(O)OP(=O)(O)CP(=O)(O)O)[C@@H](O)[C@H]3O)c2n1

Standard InChI:  InChI=1S/C12H20N5O12P3S/c1-33-12-15-9(13)6-10(16-12)17(3-14-6)11-8(19)7(18)5(28-11)2-27-32(25,26)29-31(23,24)4-30(20,21)22/h3,5,7-8,11,18-19H,2,4H2,1H3,(H,23,24)(H,25,26)(H2,13,15,16)(H2,20,21,22)/t5-,7-,8-,11-/m1/s1

Standard InChI Key:  DSYSALVZZZNDFY-IOSLPCCCSA-N

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

Properties

Molecular Weight: 551.30

Molecular Weight (Monoisotopic): 551.0042

AlogP: -0.80

#Rotatable Bonds: 9

Polar Surface Area: 269.90

Molecular Species: ACID

HBA: 14

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 17

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.38

CX Basic pKa: 5.16

CX LogP: -5.24

CX LogD: -9.39

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.11

Np Likeness Score: 0.60

References

1. Eliahu SE, Camden J, Lecka J, Weisman GA, Sévigny J, Gélinas S, Fischer B..  (2009)  Identification of hydrolytically stable and selective P2Y(1) receptor agonists.,  44  (4): [PMID:18760862] [10.1016/j.ejmech.2008.07.015]

2. Eliahu S, Barr HM, Camden J, Weisman GA, Fischer B..  (2010)  A novel insulin secretagogue based on a dinucleoside polyphosphate scaffold.,  53  (6): [PMID:20175517] [10.1021/jm901621h]

3. Eliahu S, Martín-Gil A, Perez de Lara MJ, Pintor J, Camden J, Weisman GA, Lecka J, Sévigny J, Fischer B..  (2010)  2-MeS-beta,gamma-CCl2-ATP is a potent agent for reducing intraocular pressure.,  53  (8): [PMID:20337495] [10.1021/jm100030u]

4. Lecka J, Ben-David G, Simhaev L, Eliahu S, Oscar J, Luyindula P, Pelletier J, Fischer B, Senderowitz H, Sévigny J..  (2013)  Nonhydrolyzable ATP analogues as selective inhibitors of human NPP1: a combined computational/experimental study.,  56  (21): [PMID:24083941] [10.1021/jm400918s]

Source

Source(1):

• Scientific Literature