NPASS drugs

Drug Information

Drug ID:	NPD1404
Drug Name:	Sumatriptan
Molecular Formula:	C14H21N3O2S
Canonical SMILES:	CNS(=O)(=O)Cc1ccc2c(c1)c(CCN(C)C)c[nH]2
Standard 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
Standard InCHIKey:	KQKPFRSPSRPDEB-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD1404

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient
Tanimoto coefficient is calculated based on PubChem 881-bit substructure fingerprints.

Range	Similarity Score Range
0-0.1	685
0.1-0.2	9038
0.2-0.3	14054
0.3-0.4	3598
0.4-0.5	1391
0.5-0.6	1104
0.6-0.7	682
0.7-0.8	271
0.8-0.85	46
0.85-0.9	21
0.9-0.95	0
0.95-1	0

Similar Natural Products

High Similarity Level: Tc>=0.85; Intermediate Similarity Level: 0.7 <= Tc < 0.85; Remote Similarity Level: 0.65 <= Tc < 0.7

Similarity Level	Similarity Score	Natural Product ID
High Similarity	0.8912	NPC73767
High Similarity	0.8784	NPC110126
High Similarity	0.8776	NPC84911
High Similarity	0.8766	NPC200214
High Similarity	0.875	NPC471957
High Similarity	0.8725	NPC469779
High Similarity	0.8725	NPC469768
High Similarity	0.8725	NPC469761
High Similarity	0.8725	NPC469780
High Similarity	0.8725	NPC469783
High Similarity	0.8725	NPC469767
High Similarity	0.8725	NPC469784
High Similarity	0.8707	NPC261195
High Similarity	0.8707	NPC96102
High Similarity	0.8707	NPC29886
High Similarity	0.8701	NPC470823
High Similarity	0.8701	NPC216713
High Similarity	0.8667	NPC469766
High Similarity	0.8649	NPC105127
High Similarity	0.8618	NPC314372
High Similarity	0.8609	NPC190296
Intermediate Similarity	0.8477	NPC279081
Intermediate Similarity	0.8435	NPC82295
Intermediate Similarity	0.8397	NPC24678
Intermediate Similarity	0.8397	NPC105818
Intermediate Similarity	0.8385	NPC90723
Intermediate Similarity	0.8377	NPC159856
Intermediate Similarity	0.8355	NPC230002
Intermediate Similarity	0.8313	NPC206819
Intermediate Similarity	0.8313	NPC318065
Intermediate Similarity	0.8313	NPC56765
Intermediate Similarity	0.8291	NPC469760
Intermediate Similarity	0.8291	NPC259644
Intermediate Similarity	0.8291	NPC469765
Intermediate Similarity	0.8291	NPC469763
Intermediate Similarity	0.8291	NPC25008
Intermediate Similarity	0.8291	NPC469786
Intermediate Similarity	0.8291	NPC73952
Intermediate Similarity	0.828	NPC53947
Intermediate Similarity	0.8239	NPC70922
Intermediate Similarity	0.8239	NPC75540
Intermediate Similarity	0.8239	NPC80597
Intermediate Similarity	0.8239	NPC212376
Intermediate Similarity	0.8239	NPC211572
Intermediate Similarity	0.8217	NPC321911
Intermediate Similarity	0.8205	NPC143872
Intermediate Similarity	0.8205	NPC288838
Intermediate Similarity	0.8153	NPC201380
Intermediate Similarity	0.8153	NPC469811
Intermediate Similarity	0.8153	NPC179787
Intermediate Similarity	0.8148	NPC215584
Intermediate Similarity	0.8148	NPC44773
Intermediate Similarity	0.8137	NPC469762
Intermediate Similarity	0.8137	NPC286427
Intermediate Similarity	0.8125	NPC34844
Intermediate Similarity	0.8089	NPC63545
Intermediate Similarity	0.8086	NPC41257
Intermediate Similarity	0.8075	NPC469785
Intermediate Similarity	0.8072	NPC194411
Intermediate Similarity	0.8067	NPC179365
Intermediate Similarity	0.8063	NPC141926
Intermediate Similarity	0.8049	NPC311276
Intermediate Similarity	0.8047	NPC248454
Intermediate Similarity	0.8039	NPC150259
Intermediate Similarity	0.8026	NPC198988
Intermediate Similarity	0.8	NPC22079
Intermediate Similarity	0.8	NPC470233
Intermediate Similarity	0.7988	NPC282231
Intermediate Similarity	0.7975	NPC135141
Intermediate Similarity	0.7975	NPC92796
Intermediate Similarity	0.7974	NPC325252
Intermediate Similarity	0.7974	NPC218268
Intermediate Similarity	0.7952	NPC474561
Intermediate Similarity	0.7952	NPC49954
Intermediate Similarity	0.7952	NPC160105
Intermediate Similarity	0.795	NPC325903
Intermediate Similarity	0.7947	NPC475450
Intermediate Similarity	0.7941	NPC68354
Intermediate Similarity	0.7939	NPC40779
Intermediate Similarity	0.7939	NPC194640
Intermediate Similarity	0.7933	NPC473587
Intermediate Similarity	0.7929	NPC37423
Intermediate Similarity	0.7929	NPC275305
Intermediate Similarity	0.7927	NPC279918
Intermediate Similarity	0.7922	NPC314102
Intermediate Similarity	0.7922	NPC251722
Intermediate Similarity	0.7914	NPC236711
Intermediate Similarity	0.7914	NPC216643
Intermediate Similarity	0.7911	NPC285731
Intermediate Similarity	0.7885	NPC59084
Intermediate Similarity	0.7885	NPC2949
Intermediate Similarity	0.7881	NPC475428
Intermediate Similarity	0.7867	NPC473762
Intermediate Similarity	0.7866	NPC474791
Intermediate Similarity	0.7861	NPC163055
Intermediate Similarity	0.7844	NPC49217
Intermediate Similarity	0.7834	NPC473868
Intermediate Similarity	0.7834	NPC63157
Intermediate Similarity	0.7823	NPC41174
Intermediate Similarity	0.7821	NPC88097
Intermediate Similarity	0.7818	NPC470204
Intermediate Similarity	0.7818	NPC131718
Intermediate Similarity	0.7812	NPC21605
Intermediate Similarity	0.7798	NPC201700
Intermediate Similarity	0.7798	NPC63751
Intermediate Similarity	0.7791	NPC176199
Intermediate Similarity	0.7791	NPC215795
Intermediate Similarity	0.7791	NPC38736
Intermediate Similarity	0.7771	NPC470203
Intermediate Similarity	0.7765	NPC314603
Intermediate Similarity	0.7764	NPC124005
Intermediate Similarity	0.7758	NPC230869
Intermediate Similarity	0.775	NPC316069
Intermediate Similarity	0.7738	NPC54988
Intermediate Similarity	0.7733	NPC250361
Intermediate Similarity	0.7733	NPC14113
Intermediate Similarity	0.7733	NPC84827
Intermediate Similarity	0.7733	NPC145885
Intermediate Similarity	0.7727	NPC474707
Intermediate Similarity	0.7725	NPC149265
Intermediate Similarity	0.7716	NPC33421
Intermediate Similarity	0.7711	NPC122141
Intermediate Similarity	0.7706	NPC470498
Intermediate Similarity	0.7692	NPC125746
Intermediate Similarity	0.7688	NPC470440
Intermediate Similarity	0.7688	NPC11126
Intermediate Similarity	0.7684	NPC204565
Intermediate Similarity	0.7684	NPC317030
Intermediate Similarity	0.7662	NPC473930
Intermediate Similarity	0.7658	NPC115611
Intermediate Similarity	0.7644	NPC164228
Intermediate Similarity	0.7643	NPC169433
Intermediate Similarity	0.764	NPC173028
Intermediate Similarity	0.764	NPC65215
Intermediate Similarity	0.7636	NPC51054
Intermediate Similarity	0.7619	NPC317105
Intermediate Similarity	0.7619	NPC102423
Intermediate Similarity	0.7607	NPC148592
Intermediate Similarity	0.7602	NPC82331
Intermediate Similarity	0.76	NPC233936
Intermediate Similarity	0.7593	NPC470111
Intermediate Similarity	0.759	NPC469897
Intermediate Similarity	0.7588	NPC78020
Intermediate Similarity	0.7586	NPC213468
Intermediate Similarity	0.7586	NPC265710
Intermediate Similarity	0.7578	NPC204141
Intermediate Similarity	0.7574	NPC280864
Intermediate Similarity	0.7574	NPC17751
Intermediate Similarity	0.7572	NPC267885
Intermediate Similarity	0.756	NPC16667
Intermediate Similarity	0.7558	NPC313791
Intermediate Similarity	0.7546	NPC2272
Intermediate Similarity	0.7546	NPC37548
Intermediate Similarity	0.7546	NPC187951
Intermediate Similarity	0.7543	NPC16659
Intermediate Similarity	0.7533	NPC46358
Intermediate Similarity	0.7532	NPC282398
Intermediate Similarity	0.7531	NPC129042
Intermediate Similarity	0.753	NPC184476
Intermediate Similarity	0.7529	NPC473380
Intermediate Similarity	0.7529	NPC151939
Intermediate Similarity	0.7529	NPC59269
Intermediate Similarity	0.7529	NPC240088
Intermediate Similarity	0.7527	NPC294693
Intermediate Similarity	0.7516	NPC242556
Intermediate Similarity	0.7514	NPC228835
Intermediate Similarity	0.7514	NPC149155
Intermediate Similarity	0.7514	NPC110500
Intermediate Similarity	0.7514	NPC203468
Intermediate Similarity	0.75	NPC40070
Intermediate Similarity	0.7486	NPC126709
Intermediate Similarity	0.7486	NPC248041
Intermediate Similarity	0.7483	NPC27740
Intermediate Similarity	0.7473	NPC474177
Intermediate Similarity	0.7471	NPC280852
Intermediate Similarity	0.7471	NPC474958
Intermediate Similarity	0.7471	NPC274229
Intermediate Similarity	0.7471	NPC42372
Intermediate Similarity	0.7457	NPC477611
Intermediate Similarity	0.7443	NPC300688
Intermediate Similarity	0.7443	NPC314919
Intermediate Similarity	0.7432	NPC133366
Intermediate Similarity	0.743	NPC94752
Intermediate Similarity	0.7414	NPC293216
Intermediate Similarity	0.7403	NPC95783
Intermediate Similarity	0.7396	NPC473320
Intermediate Similarity	0.7386	NPC233050
Intermediate Similarity	0.7386	NPC276540
Intermediate Similarity	0.7386	NPC283219
Intermediate Similarity	0.7375	NPC104483
Intermediate Similarity	0.7375	NPC312092
Intermediate Similarity	0.7374	NPC280290
Intermediate Similarity	0.7365	NPC470507
Intermediate Similarity	0.7353	NPC225018
Intermediate Similarity	0.7348	NPC213629
Intermediate Similarity	0.7346	NPC477977
Intermediate Similarity	0.7341	NPC280548
Intermediate Similarity	0.7341	NPC91895
Intermediate Similarity	0.7341	NPC97343
Intermediate Similarity	0.7337	NPC67056

Drug Structure

NPD1404 OpenBabel08211700192D 22 23 0 0 0 0 0 0 0 0999 V2000 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0486 1.3546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2076 0.0674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7213 -1.2708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5134 -0.2927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0827 -2.9345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9781 -1.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.1691 -3.3412 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.2565 0.3764 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9612 -4.3194 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 14 1 0 0 0 0 6 7 1 0 0 0 0 6 12 1 0 0 0 0 7 17 1 0 0 0 0 8 11 2 0 0 0 0 8 13 1 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 12 13 1 0 0 0 0 13 14 2 0 0 0 0 14 16 1 0 0 0 0 15 20 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 18 20 2 0 0 0 0 19 20 2 0 0 0 0 M END $$$$

External Identifiers

TTD	DNC001649; DAP000219; DAP001450
DrugBank	DB00669
ChEMBL	CHEMBL128
IUPHAR/BPS	54
PharmaGKB	PA451566
KEGG Drug	D00451
PubChem CID	23709079; 5358
ChEBI	10650
CAS Number	103628-46-2

Drug Properties

Molecular Weight	295.14
ALogP	-0.758
MLogP	2.34
XLogP	0.971
HDA	5
HBD	2
Rotatable Bonds	9
TPSA	73.58
RO5 Violation	0