ID: ALA216153

Max Phase: Preclinical

Molecular Formula: C17H21N4O8P

Molecular Weight: 440.35

Molecule Type: Small molecule

Representations

Canonical SMILES:  Nc1ccn([C@@H]2O[C@H](COP3(=O)OCC[C@H](c4ccncc4)O3)[C@@H](O)[C@@H]2O)c(=O)n1

Standard InChI:  InChI=1S/C17H21N4O8P/c18-13-3-7-21(17(24)20-13)16-15(23)14(22)12(28-16)9-27-30(25)26-8-4-11(29-30)10-1-5-19-6-2-10/h1-3,5-7,11-12,14-16,22-23H,4,8-9H2,(H2,18,20,24)/t11-,12-,14-,15+,16-,30?/m1/s1

Standard InChI Key:  HOAHIHGOMCBTFW-WAIXEJARSA-N

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

Properties

Molecular Weight: 440.35

Molecular Weight (Monoisotopic): 440.1097

AlogP: 0.14

#Rotatable Bonds: 5

Polar Surface Area: 168.25

Molecular Species: NEUTRAL

HBA: 12

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.56

CX Basic pKa: 4.99

CX LogP: -1.71

CX LogD: -1.71

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.54

Np Likeness Score: 0.97

References

1. Boyer SH, Sun Z, Jiang H, Esterbrook J, Gómez-Galeno JE, Craigo W, Reddy KR, Ugarkar BG, MacKenna DA, Erion MD..  (2006)  Synthesis and characterization of a novel liver-targeted prodrug of cytosine-1-beta-D-arabinofuranoside monophosphate for the treatment of hepatocellular carcinoma.,  49  (26): [PMID:17181153] [10.1021/jm0607449]

2. Boyer SH, Sun Z, Jiang H, Esterbrook J, Gómez-Galeno JE, Craigo W, Reddy KR, Ugarkar BG, MacKenna DA, Erion MD..  (2006)  Synthesis and characterization of a novel liver-targeted prodrug of cytosine-1-beta-D-arabinofuranoside monophosphate for the treatment of hepatocellular carcinoma.,  49  (26): [PMID:17181153] [10.1021/jm0607449]

Source

Source(1):

• Scientific Literature