(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-yl((2S,3R)-1-((1s,3R)-Adamantan-1-yl)-4-((4-amino-N-isobutylphenyl)-sulfonamido)-3-hydroxybutan-2-yl)carbamate

ID: ALA4581883

PubChem CID: 155561380

Max Phase: Preclinical

Molecular Formula: C31H47N3O7S

Molecular Weight: 605.80

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)CN(C[C@@H](O)[C@H](CC12CC3CC(CC(C3)C1)C2)NC(=O)O[C@H]1CO[C@H]2OCC[C@H]21)S(=O)(=O)c1ccc(N)cc1

Standard InChI:  InChI=1S/C31H47N3O7S/c1-19(2)16-34(42(37,38)24-5-3-23(32)4-6-24)17-27(35)26(15-31-12-20-9-21(13-31)11-22(10-20)14-31)33-30(36)41-28-18-40-29-25(28)7-8-39-29/h3-6,19-22,25-29,35H,7-18,32H2,1-2H3,(H,33,36)/t20?,21?,22?,25-,26-,27+,28-,29+,31?/m0/s1

Standard InChI Key:  GYALGUBWMGGMKN-OXECZZAQSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA4581883

   ---

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: 605.80

Molecular Weight (Monoisotopic): 605.3135

AlogP: 3.74

#Rotatable Bonds: 11

Polar Surface Area: 140.42

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.71

CX Basic pKa: 2.39

CX LogP: 3.52

CX LogD: 3.52

Aromatic Rings: 1

Heavy Atoms: 42

QED Weighted: 0.32

Np Likeness Score: 0.11

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