ID: ALA437508

Max Phase: Preclinical

Molecular Formula: C20H29N10O22P5

Molecular Weight: 916.37

Molecule Type: Small molecule

Representations

Canonical SMILES:  Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3cnc4c(N)ncnc43)[C@H](O)[C@@H]2O)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C20H29N10O22P5/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(47-19)1-45-53(35,36)49-55(39,40)51-57(43,44)52-56(41,42)50-54(37,38)46-2-8-12(32)14(34)20(48-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1

Standard InChI Key:  OIMACDRJUANHTJ-XPWFQUROSA-N

Molecule Features

Natural Product: Yes

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: 916.37

Molecular Weight (Monoisotopic): 916.0146

AlogP: -2.33

#Rotatable Bonds: 16

Polar Surface Area: 480.50

Molecular Species: ACID

HBA: 27

HBD: 11

#RO5 Violations: 3

HBA (Lipinski): 32

HBD (Lipinski): 13

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.59

CX Basic pKa: 5.22

CX LogP: -10.29

CX LogD: -16.97

Aromatic Rings: 4

Heavy Atoms: 57

QED Weighted: 0.05

Np Likeness Score: 0.64

References

1. Hampton A, Kappler F, Picker D..  (1982)  Species- or isozyme-specific enzyme inhibitors. 4. Design of a two-site inhibitor of adenylate kinase with isozyme selectivity.,  25  (6): [PMID:6284937] [10.1021/jm00348a006]

2. Nahum V, Tulapurkar M, Lévesque SA, Sévigny J, Reiser G, Fischer B..  (2006)  Diadenosine and diuridine poly(borano)phosphate analogues: synthesis, chemical and enzymatic stability, and activity at P2Y1 and P2Y2 receptors.,  49  (6): [PMID:16539385] [10.1021/jm050955y]

3. Yelovitch S, Camden J, Weisman GA, Fischer B..  (2012)  Boranophosphate isoster controls P2Y-receptor subtype selectivity and metabolic stability of dinucleoside polyphosphate analogues.,  55  (1): [PMID:22107038] [10.1021/jm2013198]

4. Azran S, Förster D, Danino O, Nadel Y, Reiser G, Fischer B..  (2013)  Highly efficient biocompatible neuroprotectants with dual activity as antioxidants and P2Y receptor agonists.,  56  (12): [PMID:23751098] [10.1021/jm400197m]

5. Riley AM, Unterlass J, Konieczny V, Taylor CW, Helleday T, Potter BVL..  (2018)  A synthetic diphosphoinositol phosphate analogue of inositol trisphosphate.,  9  (7): [PMID:30079174] [10.1039/C8MD00149A]

Source

Source(1):

• Scientific Literature