[[(2R,3S,4R,5R)-5-(6-amino-2-methylsulfanyl-purin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-sulfido-phosphoryl]phosphate

ID: ALA3634182

Chembl Id: CHEMBL3634182

PubChem CID: 122195891

Max Phase: Preclinical

Molecular Formula: C11H17N5O9P2S2

Molecular Weight: 489.37

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C11H17N5O9P2S2/c1-29-11-14-8(12)5-9(15-11)16(3-13-5)10-7(18)6(17)4(24-10)2-23-27(22,28)25-26(19,20)21/h3-4,6-7,10,17-18H,2H2,1H3,(H,22,28)(H2,12,14,15)(H2,19,20,21)/t4-,6-,7-,10-,27?/m1/s1

Standard InChI Key:  SNYCUVYLIGMAED-QGPPJTFUSA-N

Alternative Forms

1. Parent:

   

   ALA3634182

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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: 489.37

Molecular Weight (Monoisotopic): 488.9943

AlogP: -0.09

#Rotatable Bonds: 7

Polar Surface Area: 212.37

Molecular Species: ACID

HBA: 13

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 0.89

CX Basic pKa: 5.16

CX LogP: -3.58

CX LogD: -4.76

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.13

Np Likeness Score: 0.57

References

1. Azran S, Danino O, Förster D, Kenigsberg S, Reiser G, Dixit M, Singh V, Major DT, Fischer B..  (2015)  Identification of Highly Promising Antioxidants/Neuroprotectants Based on Nucleoside 5'-Phosphorothioate Scaffold. Synthesis, Activity, and Mechanisms of Action.,  58  (21): [PMID:26447940] [10.1021/acs.jmedchem.5b00575]

2. Azran S, Danino O, Förster D, Kenigsberg S, Reiser G, Dixit M, Singh V, Major DT, Fischer B..  (2015)  Identification of Highly Promising Antioxidants/Neuroprotectants Based on Nucleoside 5'-Phosphorothioate Scaffold. Synthesis, Activity, and Mechanisms of Action.,  58  (21): [PMID:26447940] [10.1021/acs.jmedchem.5b00575]

Source

Source(1):

• Scientific Literature