(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl((2S,3R)-1-((1s,3R)-Adamantan-1-yl)-3-hydroxy-4-((N-isobutyl-4-methoxyphenyl)sulfonamido)butan-2-yl)carbamate

ID: ALA4516606

PubChem CID: 121596962

Max Phase: Preclinical

Molecular Formula: C32H48N2O8S

Molecular Weight: 620.81

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(S(=O)(=O)N(CC(C)C)C[C@@H](O)[C@H](CC23CC4CC(CC(C4)C2)C3)NC(=O)O[C@H]2CO[C@H]3OCC[C@H]32)cc1

Standard InChI:  InChI=1S/C32H48N2O8S/c1-20(2)17-34(43(37,38)25-6-4-24(39-3)5-7-25)18-28(35)27(16-32-13-21-10-22(14-32)12-23(11-21)15-32)33-31(36)42-29-19-41-30-26(29)8-9-40-30/h4-7,20-23,26-30,35H,8-19H2,1-3H3,(H,33,36)/t21?,22?,23?,26-,27-,28+,29-,30+,32?/m0/s1

Standard InChI Key:  ZMOFGDZIKIFMEU-WWUGHDHNSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA4516606

   ---

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: 620.81

Molecular Weight (Monoisotopic): 620.3131

AlogP: 4.17

#Rotatable Bonds: 12

Polar Surface Area: 123.63

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.63

CX Basic pKa: ┄

CX LogP: 4.19

CX LogD: 4.19

Aromatic Rings: 1

Heavy Atoms: 43

QED Weighted: 0.36

Np Likeness Score: 0.08

References

1. Ghosh AK, Osswald HL, Glauninger K, Agniswamy J, Wang YF, Hayashi H, Aoki M, Weber IT, Mitsuya H..  (2016)  Probing Lipophilic Adamantyl Group as the P1-Ligand for HIV-1 Protease Inhibitors: Design, Synthesis, Protein X-ray Structural Studies, and Biological Evaluation.,  59  (14): [PMID:27389367] [10.1021/acs.jmedchem.6b00639]

Source

Source(1):

• Scientific Literature