1-beta-D-arabinofuranosyl-2-amino-4(1H)-imino-5-fluoropyrimidine 3'-phosphate

ID: ALA3229488

Chembl Id: CHEMBL3229488

PubChem CID: 90669029

Max Phase: Preclinical

Molecular Formula: C9H14FN4O7P

Molecular Weight: 340.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=c1nc(N)n([C@@H]2O[C@H](CO)[C@@H](OP(=O)(O)O)[C@@H]2O)cc1F

Standard InChI:  InChI=1S/C9H14FN4O7P/c10-3-1-14(9(12)13-7(3)11)8-5(16)6(4(2-15)20-8)21-22(17,18)19/h1,4-6,8,15-16H,2H2,(H3,11,12,13)(H2,17,18,19)/t4-,5+,6-,8-/m1/s1

Standard InChI Key:  SYLBNQJYNVXJTI-BYPJNBLXSA-N

Alternative Forms

1. Parent:

   

   ALA3229488

   [(2R,3S,4S,5R)-5-(4-amino-5-fluoro-2-iminopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] dihydrogen phosphate

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: 340.20

Molecular Weight (Monoisotopic): 340.0584

AlogP: -2.19

#Rotatable Bonds: 4

Polar Surface Area: 184.14

Molecular Species: ZWITTERION

HBA: 9

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 0.87

CX Basic pKa: 8.96

CX LogP: -2.50

CX LogD: -3.99

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.33

Np Likeness Score: 1.00

References

1. Mian AM, Long RA, Allen LB, Sidwell RW, Robins RK, Khwaja TA..  (1979)  Synthesis and antitumor and antiviral activities of 1-beta-D-arabinofuranosyl-2-amino-1,4(2H)-iminopyrimidine and its derivatives.,  22  (5): [PMID:458802] [10.1021/jm00191a011]

Source

Source(1):

• Scientific Literature