ID: ALA1233845

Max Phase: Preclinical

Molecular Formula: C33H49N2O12PS

Molecular Weight: 728.80

Molecule Type: Small molecule

Representations

Canonical SMILES:  CCOP(=O)(COc1ccc(C[C@H](NC(=O)O[C@H]2CO[C@H]3OCC[C@H]32)[C@H](O)CN(CC(C)C)S(=O)(=O)c2ccc(OC)cc2)cc1)OCC

Standard InChI:  InChI=1S/C33H49N2O12PS/c1-6-45-48(38,46-7-2)22-44-26-10-8-24(9-11-26)18-29(34-33(37)47-31-21-43-32-28(31)16-17-42-32)30(36)20-35(19-23(3)4)49(39,40)27-14-12-25(41-5)13-15-27/h8-15,23,28-32,36H,6-7,16-22H2,1-5H3,(H,34,37)/t28-,29-,30+,31-,32+/m0/s1

Standard InChI Key:  FCLYPCIMVVLLRN-FXSYQQGGSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 728.80

Molecular Weight (Monoisotopic): 728.2744

AlogP: 4.40

#Rotatable Bonds: 19

Polar Surface Area: 168.39

Molecular Species: NEUTRAL

HBA: 12

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.37

CX Basic pKa:

CX LogP: 3.82

CX LogD: 3.82

Aromatic Rings: 2

Heavy Atoms: 49

QED Weighted: 0.20

Np Likeness Score: 0.04

References

1. He G, Yang Z, Williams M, Callebaut C, Cihlar T, Murray BP, Yang C, Mitchell ML, Liu H, Wang J, Arimilli M, Eisenberg E, Stray KM, Tsai LK, Hatada M, Chen X, Chen JM, Wang Y, Lee MS, Strickley RG, Iwata Q, Zheng X, Kim CU, Swaminathan S, Desai MC, Lee WA, Xu L.  (2011)  Discovery of GS-8374, a potent human immunodeficiency virus type 1 protease inhibitor with a superior resistance profile,  2  (11): [10.1039/C1MD00147G]

2. Kryštůfek R, Šácha P, Starková J, Brynda J, Hradilek M, Tloušt'ová E, Grzymska J, Rut W, Boucher MJ, Drąg M, Majer P, Hájek M, Řezáčová P, Madhani HD, Craik CS, Konvalinka J..  (2021)  Re-emerging Aspartic Protease Targets: Examining Cryptococcus neoformans Major Aspartyl Peptidase 1 as a Target for Antifungal Drug Discovery.,  64  (10.0): [PMID:34006103] [10.1021/acs.jmedchem.0c02177]

3. Ghosh AK, Osswald HL, Prato G..  (2016)  Recent Progress in the Development of HIV-1 Protease Inhibitors for the Treatment of HIV/AIDS.,  59  (11): [PMID:26799988] [10.1021/acs.jmedchem.5b01697]

Source

Source(1):

• Scientific Literature