[(1S,2R)-1-Benzyl-3-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-2-hydroxy-propyl]-carbamic acid (3aR,4S,6aR)-(hexahydro-cyclopenta[b]furan-4-yl) ester

ID: ALA113090

PubChem CID: 461023

Max Phase: Preclinical

Molecular Formula: C32H49N3O5

Molecular Weight: 555.76

Molecule Type: Small molecule

Associated Items:

This compound is not in our inventory system

Names and Identifiers

Canonical SMILES:  CC(C)(C)NC(=O)[C@@H]1C[C@@H]2CCCC[C@@H]2CN1C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O[C@H]1CC[C@H]2OCC[C@@H]12

Standard InChI:  InChI=1S/C32H49N3O5/c1-32(2,3)34-30(37)26-18-22-11-7-8-12-23(22)19-35(26)20-27(36)25(17-21-9-5-4-6-10-21)33-31(38)40-29-14-13-28-24(29)15-16-39-28/h4-6,9-10,22-29,36H,7-8,11-20H2,1-3H3,(H,33,38)(H,34,37)/t22-,23+,24+,25-,26-,27+,28+,29-/m0/s1

Standard InChI Key:  BXHKUQJOWIKKIH-LNDVOCBLSA-N

Molfile:  

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M  END

Associated Targets(non-human)

Human immunodeficiency virus 1 (70413 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
protease Protease (2551 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
pol Human immunodeficiency virus type 1 protease (9113 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 555.76Molecular Weight (Monoisotopic): 555.3672AlogP: 4.05#Rotatable Bonds: 8
Polar Surface Area: 100.13Molecular Species: NEUTRALHBA: 6HBD: 3
#RO5 Violations: 1HBA (Lipinski): 8HBD (Lipinski): 3#RO5 Violations (Lipinski): 1
CX Acidic pKa: 13.95CX Basic pKa: 8.38CX LogP: 3.91CX LogD: 2.88
Aromatic Rings: 1Heavy Atoms: 40QED Weighted: 0.45Np Likeness Score: 0.52

References

1. Ghosh AK, Kincaid JF, Walters DE, Chen Y, Chaudhuri NC, Thompson WJ, Culberson C, Fitzgerald PM, Lee HY, McKee SP, Munson PM, Duong TT, Darke PL, Zugay JA, Schleif WA, Axel MG, Lin J, Huff JR..  (1996)  Nonpeptidal P2 ligands for HIV protease inhibitors: structure-based design, synthesis, and biological evaluation.,  39  (17): [PMID:8765511] [10.1021/jm960128k]
2. Ghosh AK..  (2009)  Harnessing nature's insight: design of aspartyl protease inhibitors from treatment of drug-resistant HIV to Alzheimer's disease.,  52  (8): [PMID:19323561] [10.1021/jm900064c]
3. Wu YJ, Meanwell NA..  (2021)  Geminal Diheteroatomic Motifs: Some Applications of Acetals, Ketals, and Their Sulfur and Nitrogen Homologues in Medicinal Chemistry and Drug Design.,  64  (14.0): [PMID:34213340] [10.1021/acs.jmedchem.1c00790]

Source