General Information of the Compound
Compound ID
CP0005653
Compound Name
(3-[2-(dimethylamino)ethyl]-1H-indol-5-yl)-N-methylmethanesulfonamide
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Synonyms
(3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl)-N-methylmethanesulfonamide
1-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide
1-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]-N-methylmethanesulfonamide
1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide
3-(2-(Dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulfonamide
3-[2-(Dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide
3-[2-(Dimethylamino)ethyl]-N-methylindole-5-methanesulfonamide
GR 43175
GR 43175X
GR-43175
Imigran (TN)
Imitrex (TN)
KS-1116
NP101
Sumatran
Sumatriptan
Sumatriptan (JAN/USP/INN)
Sumatriptanum
Sumatriptanum [INN-Latin]
Sumax
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Structure
Formula
C14H21N3O2S
Molecular Weight
295.408
Canonical SMILES
CNS(=O)(=O)Cc1ccc2[nH]cc(CCN(C)C)c2c1
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InChI
InChI=1S/C14H21N3O2S/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3/h4-5,8-9,15-16H,6-7,10H2,1-3H3
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InChIKey
KQKPFRSPSRPDEB-UHFFFAOYSA-N
CAS
103628-46-2
Physicochemical Property
logP
1.3212
Rotatable Bonds
6
Heavy Atom Count
20
Polar Areas
65.2
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Complexity
20

"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: 5358
SID: 14825017
ChEMBL ID
CHEMBL128
DrugBank ID
DB00669
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: PT00819, 5-hydroxytryptamine receptor 1A
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000017 HeLa Homo sapiens (Human)  1
1
EC50 > 1000 nM
   TI
   LI
   LO
   TS
CL000803 HA7 Homo sapiens (Human)  1
1
IC50 = 398.11 nM
   TI
   LI
   LO
   TS
CL000026 CHO-K1 Cricetulus griseus (Chinese hamster)  2
1
Ki = 341 nM
   TI
   LI
   LO
   TS
2
Ki = 440 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 Kd = 398.11 nM
2 Ki = 230 nM
3 Ki = 330 nM
4 Ki = 407.1 nM
5 Ki = 440 nM
Protein ID: PT01202, 5-hydroxytryptamine receptor 1B
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000026 CHO-K1 Cricetulus griseus (Chinese hamster)  5
1
EC50 = 77 nM
   TI
   LI
   LO
   TS
2
IC50 = 0.5012 nM
   TI
   LI
   LO
   TS
3
Ki = 9.1 nM
   TI
   LI
   LO
   TS
4
Ki = 22 nM
   TI
   LI
   LO
   TS
5
Ki = 23.1 nM
   TI
   LI
   LO
   TS
CL000011 CHO Cricetulus griseus (Chinese hamster)  3
1
IC50 = 10 nM
   TI
   LI
   LO
   TS
2
IC50 = 11 nM
   TI
   LI
   LO
   TS
3
IC50 = 16 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 27 nM
2 Ki = 7.7 nM
3 Ki = 9.6 nM
4 Ki = 10 nM
5 Ki = 19.1 nM
6 Ki = 23.1 nM
7 Ki = 36 nM
8 Ki = 47.9 nM
Protein ID: PT06668, 5-hydroxytryptamine receptor 1B
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  1
1
Ki = 6.4 nM
   TI
   LI
   LO
   TS
Protein ID: PT00827, 5-hydroxytryptamine receptor 1D
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  6
1
EC50 = 12 nM
   TI
   LI
   LO
   TS
2
EC50 = 14 nM
   TI
   LI
   LO
   TS
3
EC50 = 16 nM
   TI
   LI
   LO
   TS
4
IC50 = 5 nM
   TI
   LI
   LO
   TS
5
IC50 = 6.7 nM
   TI
   LI
   LO
   TS
6
IC50 = 6.8 nM
   TI
   LI
   LO
   TS
CL000026 CHO-K1 Cricetulus griseus (Chinese hamster)  5
1
EC50 = 30 nM
   TI
   LI
   LO
   TS
2
IC50 = 2.951 nM
   TI
   LI
   LO
   TS
3
Ki = 1.2 nM
   TI
   LI
   LO
   TS
4
Ki = 5.7 nM
   TI
   LI
   LO
   TS
5
Ki = 8.5 nM
   TI
   LI
   LO
   TS
CL000006 HEK293 Homo sapiens (Human)  1
1
Ki = 2 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 39.81 nM
2 IC50 = 100 nM
3 IC50 = 2400 nM
4 Ki = 3.4 nM
5 Ki = 4.4 nM
6 Ki = 5.5 nM
7 Ki = 8.5 nM
8 Ki = 8.6 nM
9 Ki = 11 nM
10 Ki = 23.1 nM
Protein ID: PT00957, D(2) dopamine receptor
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000026 CHO-K1 Cricetulus griseus (Chinese hamster)  1
1
Ki > 218 nM
   TI
   LI
   LO
   TS
Protein ID: PT05367, Multidrug and toxin extrusion protein 1
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  1
1
IC50 = 6700 nM
   TI
   LI
   LO
   TS
Protein ID: PT03795, Solute carrier family 22 member 1
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  1
1
Km = 55000 nM
   TI
   LI
   LO
   TS
Clinical Information about the Compound
Drug 1 ( Sumatriptan )
Drug Name Sumatriptan
Company GlaxoSmithKline
Indication
Migraine
Approved
Migraine
Phase 3
Target(s)
5-HT 1D receptor (HTR1D)
Agonist