{(1S,2R)-1-Benzyl-2-hydroxy-3-[isobutyl-(4-methoxy-benzenesulfonyl)-amino]-propyl}-carbamic acid(3R,3aS,3bR,6aS,7aS)-(octahydro-difuro[2,3-b:3',2'-d]furan-3-yl)ester

ID: ALA1232930

PubChem CID: 46891890

Max Phase: Preclinical

Molecular Formula: C30H40N2O9S

Molecular Weight: 604.72

Molecule Type: Small molecule

Associated Items:

Bioactivity Summary Target Summary Assay Summary

This compound is not in our inventory system

Names and Identifiers

Synonyms: GRL-0519 | GRL-0519|CHEMBL1232930|(3r,3as,3br,6as,7as)-Octahydrodifuro[2,3-B:3',2'-D]furan-3-Yl [(1s,2r)-1-Benzyl-2-Hydroxy-3-{[(4-Methoxyphenyl)sulfonyl](2-Methylpropyl)amino}propyl]carbamate|4hdb|4hdf|4hdp|4heg|[(3aR,3bS,4R,6aS,7aS)-2,3,3a,3b,4,5,6a,7a-octahydrodifuro[[?],[?]]furan-4-yl] N-[(1S,2R)-1-benzyl-2-hydroxy-3-[isobutyl-(4-methoxyphenyl)sulfonyl-amino]propyl]carbamate|G52|3ok9|4he9|SCHEMBL15047627|GRL-0519 & AAG|GRL-0519 & HSA|BDBM50489369|GRL-0519 & alpha1-acid glycoprotein|Q27460554Show More⌵

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

Molfile:

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M  END

Associated Targets(non-human)

protease Protease (2551 Activities)

Discover Target: protease

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

pol Human immunodeficiency virus type 1 protease (9113 Activities)

Discover Target: pol

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Human immunodeficiency virus 1 (70413 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

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

Calculated 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]

{(1S,2R)-1-Benzyl-2-hydroxy-3-[isobutyl-(4-methoxy-benzenesulfonyl)-amino]-propyl}-carbamic acid(3R,3aS,3bR,6aS,7aS)-(octahydro-difuro[2,3-b:3',2'-d]furan-3-yl)ester

Names and Identifiers

Alternative Forms

Associated Targets(non-human)

Molecule Features

Drug Indications

Mechanisms of Action

Calculated Properties

References

Source