Compound Information

General Information of the Compound

Compound ID

CP0002393

Compound Name

3-((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile

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Synonyms

Xeljanz (TN)

1-Piperi

1259404-17-5

3-((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile

3-((3R,4R)-rel-4-Methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile

3-{(3R,4R)-4-methyl-3-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl}-3-oxopropanenitrile

477600-75-2

87LA6FU830

CHEBI:71200

CHEMBL221959

CP 690550

CP-690,550

CP-690550

Tasocitinib

Tofacitinib

Tofacitinib (CP-690550,Tasocitinib)

UNII-87LA6FU830

racemic-tofacitinib

tofacitinibum

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Structure

Formula

C16H20N6O

Molecular Weight

312.377

Canonical SMILES

C[C@@H]1CCN(C[C@@H]1N(C)c1ncnc2[nH]ccc12)C(=O)CC#N

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InChI

InChI=1S/C16H20N6O/c1-11-5-8-22(14(23)3-6-17)9-13(11)21(2)16-12-4-7-18-15(12)19-10-20-16/h4,7,10-11,13H,3,5,8-9H2,1-2H3,(H,18,19,20)/t11-,13+/m1/s1

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InChIKey

UJLAWZDWDVHWOW-YPMHNXCESA-N

CAS

477600-75-2

Physicochemical Property

logP	1.54478
Rotatable Bonds	3
Heavy Atom Count	23
Polar Areas	88.91
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Complexity	23

"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: 9926791

SID: 16573063

ChEMBL ID

CHEMBL221959

DrugBank ID

DB08895

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: PT01540, Non-receptor tyrosine-protein kinase TYK2

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000132	NK-92 Cell Line Info	Homo sapiens (Human)	1
1	EC50 = 710 nM Bioactivity Info	TI LI LO TS
CL000077	Ba/F3 Cell Line Info	Mus musculus (Mouse)	2
1	GI50 = 1524 nM Bioactivity Info	TI LI LO TS
2	IC50 = 1200 nM Bioactivity Info	TI LI LO TS
CL000013	Sf9 Cell Line Info	Spodoptera frugiperda (Fall armyworm)	1
1	IC50 = 52 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	EC50 < 5 nM
2	IC50 = 3.6 nM
3	IC50 = 9 nM
4	IC50 = 10.1 nM
5	IC50 = 10.38 nM
6	IC50 = 12.8 nM
7	IC50 = 24 nM
8	IC50 = 32.3 nM
9	IC50 = 34 nM
10	IC50 = 72 nM
11	IC50 = 112 nM
12	IC50 = 260 nM
13	IC50 = 489 nM
14	Kd = 4.8 nM
15	Kd = 250 nM
16	Kd = 620 nM
17	Kd > 10000 nM
18	Ki = 4.39 nM
19	Ki = 4.4 nM
20	Ki = 7.3 nM
21	Ki = 7.8 nM

Protein ID: PT01659, Tyrosine-protein kinase JAK1

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000128	TF-1 Cell Line Info	Homo sapiens (Human)	2
1	EC50 = 43 nM Bioactivity Info	TI LI LO TS
2	EC50 = 53 nM Bioactivity Info	TI LI LO TS
CL000077	Ba/F3 Cell Line Info	Mus musculus (Mouse)	2
1	GI50 = 95.3 nM Bioactivity Info	TI LI LO TS
2	IC50 = 26 nM Bioactivity Info	TI LI LO TS
CL000013	Sf9 Cell Line Info	Spodoptera frugiperda (Fall armyworm)	2
1	IC50 = 3 nM Bioactivity Info	TI LI LO TS
2	IC50 = 110 nM Bioactivity Info	TI LI LO TS
CL000743	CellSensor STAT6-bla RA-1 Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 87 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	IC50 = 0.5 nM
2	IC50 = 0.8 nM
3	IC50 = 1.3 nM
4	IC50 = 1.4 nM
5	IC50 = 1.42 nM
6	IC50 = 1.55 nM
7	IC50 = 1.6 nM
8	IC50 = 1.7 nM
9	IC50 = 2 nM
10	IC50 = 3 nM
11	IC50 = 3.1 nM
12	IC50 = 3.2 nM
13	IC50 = 3.3 nM
14	IC50 = 3.7 nM
15	IC50 = 3.8 nM
16	IC50 = 4.1 nM
17	IC50 = 15 nM
18	IC50 = 15.1 nM
19	IC50 = 33 nM
20	IC50 = 74 nM
21	IC50 = 112 nM
22	Kd = 1.6 nM
23	Kd = 1.7 nM
24	Kd > 10000 nM
25	Ki = 0.68 nM
26	Ki = 0.7 nM

Protein ID: PT01214, Tyrosine-protein kinase JAK2

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000128	TF-1 Cell Line Info	Homo sapiens (Human)	4
1	EC50 = 93 nM Bioactivity Info	TI LI LO TS
2	IC50 = 95 nM Bioactivity Info	TI LI LO TS
3	IC50 = 120 nM Bioactivity Info	TI LI LO TS
4	IC50 = 275.1 nM Bioactivity Info	TI LI LO TS
CL000077	Ba/F3 Cell Line Info	Mus musculus (Mouse)	2
1	GI50 = 1157 nM Bioactivity Info	TI LI LO TS
2	IC50 = 265 nM Bioactivity Info	TI LI LO TS
CL000012	Sf21 Cell Line Info	Spodoptera frugiperda (Fall armyworm)	3
1	IC50 = 1.2 nM Bioactivity Info	TI LI LO TS
2	IC50 = 4 nM Bioactivity Info	TI LI LO TS
3	IC50 = 4.1 nM Bioactivity Info	TI LI LO TS
CL000131	HEK293-F Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 2.9 nM Bioactivity Info	TI LI LO TS
CL000013	Sf9 Cell Line Info	Spodoptera frugiperda (Fall armyworm)	1
1	IC50 = 4 nM Bioactivity Info	TI LI LO TS
CL000752	PBMC iPSC #1 Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 155 nM Bioactivity Info	TI LI LO TS
CL000082	HEL Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 4724 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	EC50 = 184 nM
2	IC50 = 0.5 nM
3	IC50 = 0.6 nM
4	IC50 = 1 nM
5	IC50 = 1.09 nM
6	IC50 = 1.4 nM
7	IC50 = 1.6 nM
8	IC50 = 2 nM
9	IC50 = 2.5 nM
10	IC50 = 2.7 nM
11	IC50 = 3.1 nM
12	IC50 = 4 nM
13	IC50 = 4.1 nM
14	IC50 = 4.98 nM
15	IC50 = 5 nM
16	IC50 = 7.4 nM
17	IC50 = 9.9 nM
18	IC50 = 10.7 nM
19	IC50 = 11 nM
20	IC50 = 20 nM
21	IC50 = 33 nM
22	IC50 = 38 nM
23	IC50 = 44 nM
24	IC50 = 77 nM
25	IC50 = 77.4 nM
26	IC50 = 184 nM
27	IC50 = 190 nM
28	IC50 = 302 nM
29	IC50 = 740 nM
30	Kd = 0.58 nM
31	Kd = 1.8 nM
32	Kd = 5 nM
33	Ki = 0.7 nM
34	Ki = 0.99 nM
35	Ki = 1 nM

Protein ID: PT00892, Tyrosine-protein kinase JAK3

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000077	Ba/F3 Cell Line Info	Mus musculus (Mouse)	2
1	GI50 = 503 nM Bioactivity Info	TI LI LO TS
2	IC50 = 54 nM Bioactivity Info	TI LI LO TS
CL000013	Sf9 Cell Line Info	Spodoptera frugiperda (Fall armyworm)	2
1	IC50 = 0.6 nM Bioactivity Info	TI LI LO TS
2	IC50 = 1.1 nM Bioactivity Info	TI LI LO TS
CL000129	HT-2 Cell Line Info	Mus musculus (Mouse)	1
1	IC50 = 156 nM Bioactivity Info	TI LI LO TS
CL001000	NMIi005-A Cell Line Info	Homo sapiens (Human)	1
1	IC50 = 1210 nM Bioactivity Info	TI LI LO TS

Biochemical Assays

1	EC50 < 5 nM
2	IC50 = 0.24 nM
3	IC50 = 0.29 nM
4	IC50 = 0.35 nM
5	IC50 = 0.7 nM
6	IC50 = 0.8 nM
7	IC50 = 0.98 nM
8	IC50 = 1 nM
9	IC50 = 1.1 nM
10	IC50 = 1.4 nM
11	IC50 = 1.5 nM
12	IC50 = 1.6 nM
13	IC50 = 2 nM
14	IC50 = 2.2 nM
15	IC50 = 3.2 nM
16	IC50 = 5 nM
17	IC50 = 8.5 nM
18	IC50 = 10.9 nM
19	IC50 = 13 nM
20	IC50 = 55 nM
21	IC50 = 76 nM
22	IC50 = 93.5 nM
23	IC50 >= 8000 nM
24	Kd = 0.16 nM
25	Kd = 0.7 nM
26	Kd = 2.2 nM
27	Ki = 0.2 nM
28	Ki = 0.24 nM
29	Ki = 0.4 nM
30	Ki = 1 nM

Protein ID: PT05132, Tyrosine-protein kinase JAK3

Protein Info

Cell-based Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000129	HT-2 Cell Line Info	Mus musculus (Mouse)	1
1	IC50 = 156 nM Bioactivity Info	TI LI LO TS

Cell Viability or Cytotoxicity Assay

Cell Line ID	Cell Line Name	Cell Line Organism
CL000227	HFF Cell Line Info	Homo sapiens (Human)	1
1	IC50 > 10000 nM	TI LI LO TS

Clinical Information about the Compound

Drug 1 ( Tofacitinib )

Drug Name	Tofacitinib
Company	Pfizer
Indication	Rheumatoid arthritis Approved
Target(s)	Janus kinase 3 (JAK-3) Target Info Modulator

Drug 2 ( Tofacitinib )

Drug Name	Tofacitinib
Indication	Rheumatoid arthritis Approved Coronavirus Disease 2019 (COVID-19) Phase 2

Cite

About MolBiC

Correspondence

Prof. Feng ZHU

Prof. Leo, Lianyi Han