(S)-cyclopentyl 3-(4-(((R)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(((S)-1-isopropoxy-1-oxopropan-2-yl)amino)phosphoryl)oxy)phenyl)-2-(((benzyloxy)carbonyl)amino)propanoate

ID: ALA4854086

Chembl Id: CHEMBL4854086

PubChem CID: 164615115

Max Phase: Preclinical

Molecular Formula: C37H48N7O9P

Molecular Weight: 765.80

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)OC(=O)[C@H](C)N[P@@](=O)(CO[C@H](C)Cn1cnc2c(N)ncnc21)Oc1ccc(C[C@H](NC(=O)OCc2ccccc2)C(=O)OC2CCCC2)cc1

Standard InChI:  InChI=1S/C37H48N7O9P/c1-24(2)51-35(45)26(4)43-54(48,23-50-25(3)19-44-22-41-32-33(38)39-21-40-34(32)44)53-30-16-14-27(15-17-30)18-31(36(46)52-29-12-8-9-13-29)42-37(47)49-20-28-10-6-5-7-11-28/h5-7,10-11,14-17,21-22,24-26,29,31H,8-9,12-13,18-20,23H2,1-4H3,(H,42,47)(H,43,48)(H2,38,39,40)/t25-,26+,31+,54-/m1/s1

Standard InChI Key:  VFPAMBRAQUNXEJ-VXTQKIMSSA-N

Alternative Forms

1. Parent:

   

   ALA4854086

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 765.80

Molecular Weight (Monoisotopic): 765.3251

AlogP: 5.30

#Rotatable Bonds: 18

Polar Surface Area: 208.11

Molecular Species: NEUTRAL

HBA: 14

HBD: 3

#RO5 Violations: 3

HBA (Lipinski): 16

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.35

CX Basic pKa: 4.72

CX LogP: 4.55

CX LogD: 4.55

Aromatic Rings: 4

Heavy Atoms: 54

QED Weighted: 0.07

Np Likeness Score: -0.25

References

1. Kalčic F, Zgarbová M, Hodek J, Chalupský K, Dračínský M, Dvořáková A, Strmeň T, Šebestík J, Baszczyňski O, Weber J, Mertlíková-Kaiserová H, Janeba Z..  (2021)  Discovery of Modified Amidate (ProTide) Prodrugs of Tenofovir with Enhanced Antiviral Properties.,  64  (22.0): [PMID:34713696] [10.1021/acs.jmedchem.1c01444]

Source

Source(1):

• Scientific Literature