(S)-isopropyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(4-((S)-2-(((benzyloxy)carbonyl)amino)-4-cyclopentyl-3-oxobutyl)phenoxy)phosphoryl)amino)propanoate

ID: ALA4877554

Chembl Id: CHEMBL4877554

PubChem CID: 164628937

Max Phase: Preclinical

Molecular Formula: C38H50N7O8P

Molecular Weight: 763.83

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)CC2CCCC2)cc1

Standard InChI:  InChI=1S/C38H50N7O8P/c1-25(2)52-37(47)27(4)44-54(49,24-51-26(3)20-45-23-42-34-35(39)40-22-41-36(34)45)53-31-16-14-29(15-17-31)18-32(33(46)19-28-10-8-9-11-28)43-38(48)50-21-30-12-6-5-7-13-30/h5-7,12-17,22-23,25-28,32H,8-11,18-21,24H2,1-4H3,(H,43,48)(H,44,49)(H2,39,40,41)/t26-,27+,32+,54+/m1/s1

Standard InChI Key:  PUZZUCOVCRWYQD-GZGIXZNCSA-N

Alternative Forms

1. Parent:

   

   ALA4877554

   ---

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: 763.83

Molecular Weight (Monoisotopic): 763.3458

AlogP: 5.96

#Rotatable Bonds: 19

Polar Surface Area: 198.88

Molecular Species: NEUTRAL

HBA: 13

HBD: 3

#RO5 Violations: 3

HBA (Lipinski): 15

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.36

CX Basic pKa: 4.72

CX LogP: 5.36

CX LogD: 5.36

Aromatic Rings: 4

Heavy Atoms: 54

QED Weighted: 0.07

Np Likeness Score: -0.30

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