5-(6-Amino-purin-9-yl)-3-(1-hydroxy-ethyl)-cyclopent-3-ene-1,2-diol

ID: ALA113259

Chembl Id: CHEMBL113259

Cas Number: 138662-99-4

PubChem CID: 472655

Max Phase: Preclinical

Molecular Formula: C12H15N5O3

Molecular Weight: 277.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](O)C1=C[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C12H15N5O3/c1-5(18)6-2-7(10(20)9(6)19)17-4-16-8-11(13)14-3-15-12(8)17/h2-5,7,9-10,18-20H,1H3,(H2,13,14,15)/t5-,7+,9+,10-/m0/s1

Standard InChI Key:  CDKUWLLYHVOVCD-MMBFECLISA-N

Alternative Forms

1. Parent:

   

   ALA113259

   3-Cyclopentene-1,2-diol, 5-(6-amino-9H-purin-9-yl)-3-((1S)-1-hydroxyethyl)-, (1S,2R,5R)-

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: 277.28

Molecular Weight (Monoisotopic): 277.1175

AlogP: -1.01

#Rotatable Bonds: 2

Polar Surface Area: 130.31

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.08

CX Basic pKa: 4.10

CX LogP: -1.77

CX LogD: -1.77

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.52

Np Likeness Score: 0.63

References

1. Shuto S, Obara T, Toriya M, Hosoya M, Snoeck R, Andrei G, Balzarini J, De Clercq E..  (1992)  New neplanocin analogues. 1. Synthesis of 6'-modified neplanocin A derivatives as broad-spectrum antiviral agents.,  35  (2): [PMID:1732550] [10.1021/jm00080a018]

2. Obara T, Shuto S, Saito Y, Snoeck R, Andrei G, Balzarini J, De Clercq E, Matsuda A..  (1996)  New neplanocin analogues. 7. Synthesis and antiviral activity of 2-halo derivatives of neplanocin A.,  39  (19): [PMID:8809173] [10.1021/jm960145+]

3. Shuto S, Obara T, Kosugi Y, Saito Y, Toriya M, Yaginuma S, Shigeta S, Matsuda A.  (1994)  New neplanocin analogues. III. 6R-configuration is essential for the antiviral activity of 6-C-methyl-3-deazaneplanocin a's,  4  (4): [10.1016/S0960-894X(01)80163-3]

Source

Source(1):

• Scientific Literature