Compound Information

General Information of the Compound

Compound ID

CP0043833

Compound Name

(4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one

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Synonyms

(-)-Efavirenz

(4S)-6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one

(4S)-6-Chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

(4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one

(4S)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one

(S)-6-Chloro-4-(2-cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-ben

(S)-6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one

(S)-6-Chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

2H-3,1-Benzoxazin-2-one, 6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-, (4S)-(9

6-chloro-4-(2-cyclopropyl-1-ethynyl)-4-trifluoromethyl-(4S)-1,4-dihydro-2H-benzo[d][1,3]oxazin-2-one

DMP 266

DMP-266

EFV

EFZ

Efavirenz

Efavirenz (JAN/INN)

Efavirenz, (S)-isomer

Eravirenz

L 743726

L-741211

L-743,726

L-743725

L-743726

Met-SDF-1.beta. & Efavirenz

Met-Stromal Cell-derived Factor-1.beta. (Human) & Efavirenz

Stocrin

Stocrin (TN)

Strocin (TM)

Sustiva

Sustiva (TM)

Sustiva (TN)

Zoxazin-2-one

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Structure

Formula

C14H9ClF3NO2

Molecular Weight

315.678

Canonical SMILES

FC(F)(F)[C@]1(OC(=O)Nc2ccc(Cl)cc12)C#CC1CC1

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InChI

InChI=1S/C14H9ClF3NO2/c15-9-3-4-11-10(7-9)13(14(16,17)18,21-12(20)19-11)6-5-8-1-2-8/h3-4,7-8H,1-2H2,(H,19,20)/t13-/m0/s1

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InChIKey

XPOQHMRABVBWPR-ZDUSSCGKSA-N

CAS

154598-52-4

Physicochemical Property

logP	4.0731
Rotatable Bonds	0
Heavy Atom Count	21
Polar Areas	38.33
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Complexity	21

"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: 64139

SID: 14850291

ChEMBL ID

CHEMBL223228

DrugBank ID

DB00625

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: PT00059, Envelope glycoprotein gp160

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	IC50 = 3.5 nM Bioactivity Info	TI LI LO TS

Protein ID: PT00549, Reverse transcriptase

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000247	MT-4 Cell Line Info	Homo sapiens (Human)	10
1	EC50 = 4.8 nM Bioactivity Info	TI LI LO TS
2	EC50 = 5 nM Bioactivity Info	TI LI LO TS
3	EC50 = 7 nM Bioactivity Info	TI LI LO TS
4	EC50 = 31 nM Bioactivity Info	TI LI LO TS
5	EC50 = 47.5 nM Bioactivity Info	TI LI LO TS
6	EC50 = 71 nM Bioactivity Info	TI LI LO TS
7	EC50 = 76 nM Bioactivity Info	TI LI LO TS
8	EC50 = 171.1 nM Bioactivity Info	TI LI LO TS
9	EC50 = 260 nM Bioactivity Info	TI LI LO TS
10	EC50 = 380 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	IC50 = 10 nM
2	IC50 = 20 nM
3	IC50 = 100 nM
4	IC50 = 120 nM
5	IC50 = 170 nM

Protein ID: PT00005, Reverse transcriptase/RNaseH

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000247	MT-4 Cell Line Info	Homo sapiens (Human)	23
1	EC50 = 1 nM Bioactivity Info	TI LI LO TS
2	EC50 = 2.85 nM Bioactivity Info	TI LI LO TS
3	EC50 = 4 nM Bioactivity Info	TI LI LO TS
4	EC50 = 5 nM Bioactivity Info	TI LI LO TS
5	EC50 = 5.19 nM Bioactivity Info	TI LI LO TS
6	EC50 = 5.2 nM Bioactivity Info	TI LI LO TS
7	EC50 = 8.2 nM Bioactivity Info	TI LI LO TS
8	EC50 = 16 nM Bioactivity Info	TI LI LO TS
9	EC50 = 29 nM Bioactivity Info	TI LI LO TS
10	EC50 = 38 nM Bioactivity Info	TI LI LO TS
11	EC50 = 44 nM Bioactivity Info	TI LI LO TS
12	EC50 = 57 nM Bioactivity Info	TI LI LO TS
13	EC50 = 80.1 nM Bioactivity Info	TI LI LO TS
14	EC50 = 115 nM Bioactivity Info	TI LI LO TS
15	EC50 = 160 nM Bioactivity Info	TI LI LO TS
16	EC50 = 200 nM Bioactivity Info	TI LI LO TS
17	EC50 = 224 nM Bioactivity Info	TI LI LO TS
18	EC50 = 300 nM Bioactivity Info	TI LI LO TS
19	EC50 = 308 nM Bioactivity Info	TI LI LO TS
20	EC50 = 348 nM Bioactivity Info	TI LI LO TS
21	EC50 = 514 nM Bioactivity Info	TI LI LO TS
22	IC50 = 4 nM Bioactivity Info	TI LI LO TS
23	IC50 = 6 nM Bioactivity Info	TI LI LO TS
CL000025	HEK-293T Cell Line Info	Homo sapiens (Human)	3
1	IC50 = 6 nM Bioactivity Info	TI LI LO TS
2	IC50 = 9.5 nM Bioactivity Info	TI LI LO TS
3	IC50 = 54 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	EC50 = 1 nM
2	EC50 = 4 nM
3	EC50 = 5.4 nM
4	EC50 = 44.7 nM
5	EC50 = 91.5 nM
6	EC50 = 156.17 nM
7	IC50 = 0.091 nM
8	IC50 = 0.166 nM
9	IC50 = 0.42 nM
10	IC50 = 0.75 nM
11	IC50 = 1 nM
12	IC50 = 1.3 nM
13	IC50 = 2 nM
14	IC50 = 3 nM
15	IC50 = 4 nM
16	IC50 = 6 nM
17	IC50 = 7 nM
18	IC50 = 7.2 nM
19	IC50 = 8 nM
20	IC50 = 9.503294 nM
21	IC50 = 10 nM
22	IC50 = 11 nM
23	IC50 = 12 nM
24	IC50 = 14 nM
25	IC50 = 17 nM
26	IC50 = 18 nM
27	IC50 = 20 nM
28	IC50 = 22 nM
29	IC50 = 22.174354 nM
30	IC50 = 24 nM
31	IC50 = 30 nM
32	IC50 = 35 nM
33	IC50 = 38 nM
34	IC50 = 40 nM
35	IC50 = 44 nM
36	IC50 = 47 nM
37	IC50 = 48 nM
38	IC50 = 50 nM
39	IC50 = 57 nM
40	IC50 = 61 nM
41	IC50 = 80 nM
42	IC50 = 93 nM
43	IC50 = 120 nM
44	IC50 = 180 nM
45	IC50 = 280 nM
46	IC50 = 360 nM
47	IC50 = 400 nM
48	IC50 = 480 nM
49	IC50 = 500 nM
50	IC50 = 680 nM
51	IC50 = 800 nM
52	IC50 = 1520 nM
53	IC50 = 2100 nM
54	IC50 > 20000 nM
55	IC50 > 100000 nM
56	Ki = 0.4 nM
57	Ki = 2.93 nM
58	Ki = 3 nM
59	Ki = 4 nM
60	Ki = 30 nM
61	Ki = 40 nM
62	Ki = 120 nM
63	Ki = 150 nM
64	Ki = 160 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 > 320 nM	TI LI LO TS

Clinical Information about the Compound

Drug 1 ( Efavirenz )

Drug Name	Efavirenz
Indication	Human immunodeficiency virus infection Approved

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About MolBiC

Correspondence

Prof. Feng ZHU

Prof. Leo, Lianyi Han