2-(6-Amino-9H-purin-3-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-carbonitrile

ID: ALA337389

Chembl Id: CHEMBL337389

PubChem CID: 44355029

Max Phase: Preclinical

Molecular Formula: C11H12N6O3

Molecular Weight: 276.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C[C@H]1[C@H](O)[C@@H](CO)O[C@H]1n1cnc2c(N)ncnc21

Standard InChI:  InChI=1S/C11H12N6O3/c12-1-5-8(19)6(2-18)20-11(5)17-4-16-7-9(13)14-3-15-10(7)17/h3-6,8,11,18-19H,2H2,(H2,13,14,15)/t5-,6+,8-,11+/m0/s1

Standard InChI Key:  RRPRIYZEGMMNAK-MCOSLZNDSA-N

Alternative Forms

1. Parent:

   

   ALA337389

   (2R,3S,4S,5R)-2-(6-aminopurin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolane-3-carbonitrile

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: 276.26

Molecular Weight (Monoisotopic): 276.0971

AlogP: -1.20

#Rotatable Bonds: 2

Polar Surface Area: 143.10

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.11

CX Basic pKa: 3.95

CX LogP: -1.74

CX LogD: -1.74

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.62

Np Likeness Score: 0.82

References

1. Azuma A, Nakajima Y, Nishizono N, Minakawa N, Suzuki M, Hanaoka K, Kobayashi T, Tanaka M, Sasaki T, Matsuda A..  (1993)  Nucleosides and nucleotides. 122. 2'-C-cyano-2'-deoxy-1-beta-D-arabinofuranosylcytosine and its derivatives. A new class of nucleoside with a broad antitumor spectrum.,  36  (26): [PMID:8277499] [10.1021/jm00078a006]

2. Ohtawa M, Ichikawa S, Teishikata Y, Fujimuro M, Yokosawa H, Matsuda A..  (2007)  9-(2-C-Cyano-2-deoxy-beta-D-arabino-pentofuranosyl)guanine, a potential antitumor agent against B-lymphoma infected with Kaposi's sarcoma-associated herpesvirus.,  50  (9): [PMID:17402726] [10.1021/jm070032y]

Source

Source(1):

• Scientific Literature