ID: ALA1232930

Max Phase: Preclinical

Molecular Formula: C30H40N2O9S

Molecular Weight: 604.72

Molecule Type: Small molecule

Representations

Synonyms (1): GRL-0519
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1ccc(S(=O)(=O)N(CC(C)C)C[C@@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CO[C@H]3O[C@@H]4OCC[C@@H]4[C@H]32)cc1

Standard InChI:  InChI=1S/C30H40N2O9S/c1-19(2)16-32(42(35,36)22-11-9-21(37-3)10-12-22)17-25(33)24(15-20-7-5-4-6-8-20)31-30(34)40-26-18-39-29-27(26)23-13-14-38-28(23)41-29/h4-12,19,23-29,33H,13-18H2,1-3H3,(H,31,34)/t23-,24+,25-,26+,27+,28+,29+/m1/s1

Standard InChI Key:  QWMNYFXRFHGYGS-DDGGWZRMSA-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: 604.72

Molecular Weight (Monoisotopic): 604.2455

AlogP: 2.77

#Rotatable Bonds: 12

Polar Surface Area: 132.86

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.48

CX Basic pKa:

CX LogP: 3.54

CX LogD: 3.54

Aromatic Rings: 2

Heavy Atoms: 42

QED Weighted: 0.38

Np Likeness Score: 0.10

References

1. Zhang H, Wang YF, Shen CH, Agniswamy J, Rao KV, Xu CX, Ghosh AK, Harrison RW, Weber IT..  (2013)  Novel P2 tris-tetrahydrofuran group in antiviral compound 1 (GRL-0519) fills the S2 binding pocket of selected mutants of HIV-1 protease.,  56  (3): [PMID:23298236] [10.1021/jm301519z]

2. Agniswamy J, Shen CH, Wang YF, Ghosh AK, Rao KV, Xu CX, Sayer JM, Louis JM, Weber IT..  (2013)  Extreme multidrug resistant HIV-1 protease with 20 mutations is resistant to novel protease inhibitors with P1'-pyrrolidinone or P2-tris-tetrahydrofuran.,  56  (10): [PMID:23590295] [10.1021/jm400231v]

3. Ghosh AK, Parham GL, Martyr CD, Nyalapatla PR, Osswald HL, Agniswamy J, Wang YF, Amano M, Weber IT, Mitsuya H..  (2013)  Highly potent HIV-1 protease inhibitors with novel tricyclic P2 ligands: design, synthesis, and protein-ligand X-ray studies.,  56  (17): [PMID:23947685] [10.1021/jm400768f]

4. 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]

5. 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