General Information of the Compound
Compound ID
CP0644596
Compound Name
LEDIPASVIR
    Show/Hide
Synonyms
013TE6E4WV
1256388-51-8
CHEBI:85089
CHEMBL2374220
DTXSID90154829
EX-A411
GS 5885
GS-5885
GS5885
Ledipasvir
Ledipasvir (GS5885)
Ledipasvir (USAN)
Ledipasvir [USAN:INN]
MolPort-039-138-665
SCHEMBL15116943
SCHEMBL2706494
UNII-013TE6E4WV
WHO 9796
methyl [(2S)-1-{(6S)-6-[4-(9,9-difluoro-7-{2-[(1R,3S,4S)-2-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-azabicyclo[2.2.1]hept-3-yl]-1H-benzimidazol-5-yl}-9H-fluoren-2-yl)-1H-imidazol-2-yl]-5-azaspiro[2.4]hept-5-yl}-3-methyl-1-oxobutan-2-yl]carbamate
    Show/Hide
Structure
Formula
C49H54F2N8O6
Molecular Weight
889.017
Canonical SMILES
COC(=O)N[C@H](C(=O)N1CC2(CC2)C[C@H]1c1nc(-c2ccc3c(c2)C(F)(F)c2cc(-c4ccc5[nH]c([C@@H]6[C@H]7CC[C@H](C7)N6C(=O)[C@@H](NC(=O)OC)C(C)C)nc5c4)ccc2-3)c[nH]1)C(C)C
    Show/Hide
InChI
InChI=1S/C49H54F2N8O6/c1-24(2)39(56-46(62)64-5)44(60)58-23-48(15-16-48)21-38(58)42-52-22-37(55-42)28-9-13-32-31-12-8-26(18-33(31)49(50,51)34(32)19-28)27-10-14-35-36(20-27)54-43(53-35)41-29-7-11-30(17-29)59(41)45(61)40(25(3)4)57-47(63)65-6/h8-10,12-14,18-20,22,24-25,29-30,38-41H,7,11,15-17,21,23H2,1-6H3,(H,52,55)(H,53,54)(H,56,62)(H,57,63)/t29-,30+,38-,39-,40-,41-/m0/s1
    Show/Hide
InChIKey
VRTWBAAJJOHBQU-KMWAZVGDSA-N
CAS
1256388-51-8
Physicochemical Property
logP
8.6073
Rotatable Bonds
10
Heavy Atom Count
65
Polar Areas
174.64
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
8
Complexity
65

"RO5" indicates the cutoff set by lipinski's rule of five:

(1) Molecular weight less than 500 Dalton;

(2) xlogp less than 5;

(3) No more than 5 hbonddonor (Hydrogen Bond Donor Count);

(4) No more than 10 hbondacc (Hydrogen Bond Acceptor Count);

(5) No more than 10 rotbonds (Rotatable Bond Count).

    Show/Hide
Click to Show/Hide the External Link(s) of This Compound
PubChem ID
CID: 67505836
ChEMBL ID
CHEMBL2374220
DrugBank ID
DB09027
Map of Molecular Bioactivity Related to the Compound
Map of Molecular Bioactivity Related to the Compound

Compound
Cell Line
Protein

Bioactivity Value:

<= 0.1 μM
> 0.1 μM and <= 10 μM
> 10 μM
Imprecise Activity
Table of Molecular Bioactivities Related to the Compound
Protein ID: PT00149, Nonstructural protein 5A
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000148 Huh-7 Homo sapiens (Human)  27
1
EC50 = 0.031 nM
   TI
   LI
   LO
   TS
2
EC50 = 0.15 nM
   TI
   LI
   LO
   TS
3
EC50 = 0.39 nM
   TI
   LI
   LO
   TS
4
EC50 = 1.1 nM
   TI
   LI
   LO
   TS
5
EC50 = 1.9 nM
   TI
   LI
   LO
   TS
6
EC50 = 5.7 nM
   TI
   LI
   LO
   TS
7
EC50 = 7.2 nM
   TI
   LI
   LO
   TS
8
EC50 = 17 nM
   TI
   LI
   LO
   TS
9
EC50 = 19.6 nM
   TI
   LI
   LO
   TS
10
EC50 = 21 nM
   TI
   LI
   LO
   TS
11
EC50 = 49.6 nM
   TI
   LI
   LO
   TS
12
EC50 = 52 nM
   TI
   LI
   LO
   TS
13
EC50 = 123 nM
   TI
   LI
   LO
   TS
14
EC50 = 164 nM
   TI
   LI
   LO
   TS
15
EC50 = 168 nM
   TI
   LI
   LO
   TS
16
EC50 = 169 nM
   TI
   LI
   LO
   TS
17
EC50 = 209 nM
   TI
   LI
   LO
   TS
18
EC50 = 211 nM
   TI
   LI
   LO
   TS
19
EC50 = 222 nM
   TI
   LI
   LO
   TS
20
EC50 = 249 nM
   TI
   LI
   LO
   TS
21
EC50 = 264 nM
   TI
   LI
   LO
   TS
22
EC50 = 292 nM
   TI
   LI
   LO
   TS
23
EC50 = 530 nM
   TI
   LI
   LO
   TS
24
EC50 = 865 nM
   TI
   LI
   LO
   TS
25
EC50 = 943 nM
   TI
   LI
   LO
   TS
26
EC50 > 44.8 nM
   TI
   LI
   LO
   TS
27
EC50 > 88.8 nM
   TI
   LI
   LO
   TS
Clinical Information about the Compound
Drug 1 ( GS-5885 )
Drug Name GS-5885
Company Gilead Sciences Inc
Indication
Hepatitis C virus infection
Phase 2