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Also known as: Danoprevir, 850876-88-9, Schembl2833159, Zinc150357979, Cs-0337, Ac-32903

Molecular Formula

C₃₅H₄₆FN₅O₉S

Molecular Weight

731.8 g/mol

InChI Key

ZVTDLPBHTSMEJZ-AIYSODCISA-N

Danoprevir is an orally bioavailable, peptidomimetic inhibitor of hepatitis C virus (HCV) NS3/4A protease, with antiviral activity against HCV and potential antiviral activity against SARS-CoV-2. Upon oral administration, danoprevir binds to and blocks the activity of HCV NS3/4A protease. This prevents the cleavage and processing of HCV viral proteins leading to the inhibition of HCV replication. Danoprevir may also bind to and block of the activity of SARS-CoV-2 protease. This prevents the cleavage and processing of SARS-CoV-2 viral proteins leading to the inhibition of SARS-CoV-2 replication. NS3/4A, a chymotrypsin-like serine protease, is responsible for cleavage at four sites of the HCV polyprotein to form the viral proteins required for HCV replication. It plays a key role in the HCV viral replication process. HCV infection is associated with the development of hepatocellular carcinoma (HCC). A chymotrypsin-like protease is responsible for cleavage of the SARS-CoV-2 viral polyprotein to form the RNA replicase-transcriptase complex, which plays a key role in the SARS-CoV-2 viral transcription and replication process.

1 2D Structure

Danoprevir

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(1S,4R,6S,7E,14S,18R)-4-(cyclopropylsulfonylcarbamoyl)-14-[(2-methylpropan-2-yl)oxycarbonylamino]-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-en-18-yl] 4-fluoro-1,3-dihydroisoindole-2-carboxylate

2.1.2 InChI

InChI=1S/C35H46FN5O9S/c1-34(2,3)50-32(45)37-27-13-8-6-4-5-7-11-22-17-35(22,31(44)39-51(47,48)24-14-15-24)38-29(42)28-16-23(19-41(28)30(27)43)49-33(46)40-18-21-10-9-12-26(36)25(21)20-40/h7,9-12,22-24,27-28H,4-6,8,13-20H2,1-3H3,(H,37,45)(H,38,42)(H,39,44)/b11-7+/t22-,23-,27+,28+,35-/m1/s1

2.1.3 InChI Key

ZVTDLPBHTSMEJZ-AIYSODCISA-N

2.1.4 Canonical SMILES

CC(C)(C)OC(=O)NC1CCCCCC=CC2CC2(NC(=O)C3CC(CN3C1=O)OC(=O)N4CC5=C(C4)C(=CC=C5)F)C(=O)NS(=O)(=O)C6CC6

2.1.5 Isomeric SMILES

CC(C)(C)OC(=O)N[C@H]1CCCCC/C=C/[C@@H]2C[C@]2(NC(=O)[C@@H]3C[C@H](CN3C1=O)OC(=O)N4CC5=C(C4)C(=CC=C5)F)C(=O)NS(=O)(=O)C6CC6

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Danoprevir

2. Itmn 191

3. Itmn-191

4. Itmn191

5. R 7227

6. R-7227

7. R7227 Cpd

8. Rg 7227

9. Rg-7227

10. Rg7227

2.2.2 Depositor-Supplied Synonyms

1. Danoprevir

2. 850876-88-9

3. Schembl2833159

4. Zinc150357979

5. Cs-0337

6. Ac-32903

7. Hy-10238

8. 2h-isoindole-2-carboxylic Acid, 4-fluoro-1,3-dihydro-, (2r,6s,13as,14ar,16as)-14a-[[(cyclopropylsulfonyl)amino]carbonyl]-6-[[(1,1-dimethylethoxy)carbonyl]amino]-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydro-5,16-dioxocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-2-yl Ester

2.3 Create Date

2011-11-16

3 Chemical and Physical Properties

Molecular Formula	C₃₅H₄₆FN₅O₉S
Molecular Weight	731.8 g/mol
XLogP3	3.3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	8
Exact Mass	731.30002740 g/mol
Monoisotopic Mass	731.30002740 g/mol
Topological Polar Surface Area	189 Å²
Heavy Atom Count	51
Formal Charge	0
Complexity	1530
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1