General Information of the Compound
Compound ID
CP0132905
Compound Name
Rilpivirine
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Synonyms
RPV
(E)-4-((4-((4-(2-cyanovinyl)-2,6-dimethylphenyl)amino)pyrimidin-2-yl)amino)benzonitrile
(E)-4-(4-(4-(2-cyanovinyl)-2,6-dimethylphenylamino)pyrimidin-2-ylamino)benzonitrile
4-{[4-({4-[(E)-2-Cyanoethenyl]-2,6-Dimethylphenyl}amino)pyrimidin-2-Yl]amino}benzonitrile
4-{[4-({4-[(E)-2-cyanovinyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile
500287-72-9
CHEBI:68606
Edurant
FI96A8X663
Mu O-conotoxin
R 278474
R278474
Rilpivirine
TMC 278
TMC-278
TMC278
UNII-FI96A8X663
W-202888
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Structure
Formula
C22H18N6
Molecular Weight
366.428
Canonical SMILES
Cc1cc(\C=C\C#N)cc(C)c1Nc1ccnc(Nc2ccc(cc2)C#N)n1
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InChI
InChI=1S/C22H18N6/c1-15-12-18(4-3-10-23)13-16(2)21(15)27-20-9-11-25-22(28-20)26-19-7-5-17(14-24)6-8-19/h3-9,11-13H,1-2H3,(H2,25,26,27,28)/b4-3+
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InChIKey
YIBOMRUWOWDFLG-ONEGZZNKSA-N
CAS
500287-72-9
Physicochemical Property
logP
4.9891
Rotatable Bonds
5
Heavy Atom Count
28
Polar Areas
97.42
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
6
Complexity
28

"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).

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PubChem ID
CID: 6451164
SID: 14926256
ChEMBL ID
CHEMBL175691
DrugBank ID
DB08864
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: PT00005, Reverse transcriptase/RNaseH
 Protein Info 
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000599 TZM-bl
 Cell Line Info 
Homo sapiens (Human)  1
1
EC50 = 3.55 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 EC50 = 0.4 nM
2 IC50 = 1 nM
3 IC50 = 15 nM
4 IC50 = 21 nM
5 IC50 = 22 nM
6 IC50 = 23 nM
7 IC50 = 24 nM
8 IC50 = 27 nM
9 IC50 = 38 nM
10 IC50 = 41 nM
11 IC50 = 42 nM
12 IC50 = 84 nM
13 IC50 > 10000 nM
Cell Viability or Cytotoxicity Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000247 MT-4
 Cell Line Info 
Homo sapiens (Human)  1
1
CC50 = 3980 nM
   TI
   LI
   LO
   TS
Clinical Information about the Compound
Drug 1 ( Rilpivirine )
Drug Name Rilpivirine
Indication
Human immunodeficiency virus infection
Approved
Pain
Investigative
Target(s)
Voltage-gated sodium channel alpha Nav1.8 (SCN10A)
 Target Info 
Inhibitor