NPASS drugs

Drug Information

Drug ID:	NPD6646
Drug Name:	napsagatran
Molecular Formula:	C26H34N6O6S
Canonical SMILES:	OC(=O)CN(C(=O)[C@@H](NS(=O)(=O)c1ccc2c(c1)cccc2)CC(=NC[C@@H]1CCCN(C1)C(=N)N)O)C1CC1
Standard InCHI:	InChI=1S/C26H34N6O6S/c27-26(28)31-11-3-4-17(15-31)14-29-23(33)13-22(25(36)32(16-24(34)35)20-8-9-20)30-39(37,38)21-10-7-18-5-1-2-6-19(18)12-21/h1-2,5-7,10,12,17,20,22,30H,3-4,8-9,11,13-16H2,(H3,27,28)(H,29,33)(H,34,35)/t17-,22-/m0/s1
Standard InCHIKey:	BYDKEYCXCIVOOV-JTSKRJEESA-N
Max Developmental Stage:	Discontinued
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD6646

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	165
0.1-0.2	1283
0.2-0.3	9625
0.3-0.4	15466
0.4-0.5	3679
0.5-0.6	536
0.6-0.7	132
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
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
Intermediate Similarity	0.7188	NPC132636
Intermediate Similarity	0.7089	NPC32858
Intermediate Similarity	0.7089	NPC194857
Intermediate Similarity	0.703	NPC314114
Remote Similarity	0.6914	NPC217804
Remote Similarity	0.6914	NPC22883
Remote Similarity	0.6914	NPC210377
Remote Similarity	0.6914	NPC5719
Remote Similarity	0.6883	NPC71684
Remote Similarity	0.6879	NPC62104
Remote Similarity	0.6879	NPC1390
Remote Similarity	0.6875	NPC15068
Remote Similarity	0.6836	NPC63040
Remote Similarity	0.6821	NPC324850
Remote Similarity	0.6776	NPC470544
Remote Similarity	0.6772	NPC477937
Remote Similarity	0.6732	NPC470545
Remote Similarity	0.6725	NPC300443
Remote Similarity	0.6688	NPC470546
Remote Similarity	0.6686	NPC311658
Remote Similarity	0.6648	NPC471527
Remote Similarity	0.659	NPC286551
Remote Similarity	0.6584	NPC111428
Remote Similarity	0.6568	NPC322878
Remote Similarity	0.6494	NPC473341
Remote Similarity	0.6492	NPC61332
Remote Similarity	0.6492	NPC240130
Remote Similarity	0.6484	NPC276506
Remote Similarity	0.6484	NPC198254
Remote Similarity	0.6484	NPC274198
Remote Similarity	0.6481	NPC473322
Remote Similarity	0.6461	NPC475544
Remote Similarity	0.6461	NPC469243
Remote Similarity	0.6452	NPC239357
Remote Similarity	0.6446	NPC314835
Remote Similarity	0.6444	NPC223207
Remote Similarity	0.6432	NPC196243
Remote Similarity	0.6429	NPC163392
Remote Similarity	0.6429	NPC239762
Remote Similarity	0.6425	NPC73655
Remote Similarity	0.6417	NPC153554
Remote Similarity	0.6409	NPC290755
Remote Similarity	0.6409	NPC471771
Remote Similarity	0.6409	NPC304074
Remote Similarity	0.6407	NPC127741
Remote Similarity	0.6404	NPC24617
Remote Similarity	0.6398	NPC101719
Remote Similarity	0.6392	NPC302715
Remote Similarity	0.6374	NPC315266
Remote Similarity	0.6369	NPC114806
Remote Similarity	0.6358	NPC105717
Remote Similarity	0.6335	NPC22746
Remote Similarity	0.6335	NPC222466
Remote Similarity	0.6328	NPC473580
Remote Similarity	0.6303	NPC255447
Remote Similarity	0.6296	NPC473404
Remote Similarity	0.6289	NPC200964
Remote Similarity	0.6279	NPC209509
Remote Similarity	0.6269	NPC102959
Remote Similarity	0.6257	NPC161069
Remote Similarity	0.6257	NPC468984
Remote Similarity	0.6242	NPC300315
Remote Similarity	0.6242	NPC200589
Remote Similarity	0.6237	NPC60516
Remote Similarity	0.6237	NPC475532
Remote Similarity	0.6236	NPC469903
Remote Similarity	0.6235	NPC476259
Remote Similarity	0.6221	NPC52748
Remote Similarity	0.622	NPC319766
Remote Similarity	0.6215	NPC122590
Remote Similarity	0.6209	NPC471053
Remote Similarity	0.6209	NPC471052
Remote Similarity	0.6209	NPC471051
Remote Similarity	0.6203	NPC165285
Remote Similarity	0.6194	NPC474584
Remote Similarity	0.6193	NPC477632
Remote Similarity	0.6193	NPC477638
Remote Similarity	0.619	NPC141050
Remote Similarity	0.6176	NPC470884
Remote Similarity	0.6176	NPC92784
Remote Similarity	0.6176	NPC98424
Remote Similarity	0.6176	NPC178662
Remote Similarity	0.6176	NPC476133
Remote Similarity	0.6173	NPC6975
Remote Similarity	0.6169	NPC319579
Remote Similarity	0.6163	NPC77905
Remote Similarity	0.6163	NPC176226
Remote Similarity	0.6162	NPC280022
Remote Similarity	0.6149	NPC202521
Remote Similarity	0.6149	NPC262077
Remote Similarity	0.6134	NPC94862
Remote Similarity	0.6118	NPC471265
Remote Similarity	0.6118	NPC471264
Remote Similarity	0.6118	NPC68865
Remote Similarity	0.6117	NPC17698
Remote Similarity	0.6114	NPC138775
Remote Similarity	0.6105	NPC119652
Remote Similarity	0.6105	NPC469427
Remote Similarity	0.6105	NPC263493
Remote Similarity	0.6105	NPC469426
Remote Similarity	0.6105	NPC97526
Remote Similarity	0.6105	NPC168113
Remote Similarity	0.6105	NPC269398
Remote Similarity	0.6099	NPC469902
Remote Similarity	0.6087	NPC476990
Remote Similarity	0.6082	NPC89489
Remote Similarity	0.608	NPC471820
Remote Similarity	0.608	NPC471821
Remote Similarity	0.6075	NPC129486
Remote Similarity	0.6069	NPC139326
Remote Similarity	0.6069	NPC197682
Remote Similarity	0.6054	NPC61004
Remote Similarity	0.6053	NPC473418
Remote Similarity	0.6045	NPC13470
Remote Similarity	0.6045	NPC2501
Remote Similarity	0.6043	NPC40234
Remote Similarity	0.6038	NPC14672
Remote Similarity	0.6038	NPC285926
Remote Similarity	0.6038	NPC315276
Remote Similarity	0.6026	NPC329011
Remote Similarity	0.602	NPC477550
Remote Similarity	0.602	NPC477552
Remote Similarity	0.6013	NPC327481
Remote Similarity	0.6013	NPC33742
Remote Similarity	0.6012	NPC130309
Remote Similarity	0.6012	NPC252878
Remote Similarity	0.6011	NPC475168
Remote Similarity	0.6011	NPC7817
Remote Similarity	0.6	NPC313867
Remote Similarity	0.6	NPC189116
Remote Similarity	0.6	NPC316008
Remote Similarity	0.6	NPC254088
Remote Similarity	0.6	NPC329295
Remote Similarity	0.6	NPC50016
Remote Similarity	0.6	NPC63931
Remote Similarity	0.6	NPC473002
Remote Similarity	0.599	NPC477636
Remote Similarity	0.599	NPC469444
Remote Similarity	0.5989	NPC469904
Remote Similarity	0.5979	NPC273755
Remote Similarity	0.5979	NPC306804
Remote Similarity	0.5976	NPC35996
Remote Similarity	0.5976	NPC46427
Remote Similarity	0.5976	NPC325479
Remote Similarity	0.5976	NPC246079
Remote Similarity	0.5969	NPC473001
Remote Similarity	0.5966	NPC314358
Remote Similarity	0.5963	NPC220698
Remote Similarity	0.5961	NPC477551
Remote Similarity	0.5957	NPC46009
Remote Similarity	0.5954	NPC268841
Remote Similarity	0.5954	NPC307357
Remote Similarity	0.5954	NPC46098
Remote Similarity	0.5949	NPC276949
Remote Similarity	0.5949	NPC35850
Remote Similarity	0.5947	NPC158277
Remote Similarity	0.5943	NPC315283
Remote Similarity	0.5943	NPC314388
Remote Similarity	0.5941	NPC287401
Remote Similarity	0.5936	NPC294516
Remote Similarity	0.5936	NPC107938
Remote Similarity	0.593	NPC477631
Remote Similarity	0.5924	NPC469901
Remote Similarity	0.5924	NPC473003
Remote Similarity	0.592	NPC477639
Remote Similarity	0.5912	NPC470902
Remote Similarity	0.5909	NPC5620
Remote Similarity	0.5909	NPC201244
Remote Similarity	0.5909	NPC477217
Remote Similarity	0.5907	NPC478007
Remote Similarity	0.5907	NPC475409
Remote Similarity	0.5907	NPC170302
Remote Similarity	0.5907	NPC475564
Remote Similarity	0.5905	NPC469445
Remote Similarity	0.5902	NPC323336
Remote Similarity	0.5902	NPC197743
Remote Similarity	0.5902	NPC297145
Remote Similarity	0.5902	NPC326349
Remote Similarity	0.5899	NPC240848
Remote Similarity	0.589	NPC302169
Remote Similarity	0.5885	NPC473546
Remote Similarity	0.5885	NPC14849
Remote Similarity	0.5879	NPC175726
Remote Similarity	0.5879	NPC474082
Remote Similarity	0.5875	NPC197470
Remote Similarity	0.5873	NPC475123
Remote Similarity	0.5873	NPC475204
Remote Similarity	0.5866	NPC254798
Remote Similarity	0.5864	NPC328611
Remote Similarity	0.5864	NPC314992
Remote Similarity	0.5864	NPC476227
Remote Similarity	0.5864	NPC326407
Remote Similarity	0.5864	NPC317725
Remote Similarity	0.5862	NPC48202
Remote Similarity	0.5855	NPC182057
Remote Similarity	0.5855	NPC147298
Remote Similarity	0.5855	NPC45037
Remote Similarity	0.5855	NPC269750
Remote Similarity	0.5855	NPC131450
Remote Similarity	0.5855	NPC194671

Drug Structure

NPD6646 OpenBabel08211710072D 45 48 0 0 1 0 0 0 0 0999 V2000 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -4.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8660 -2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8660 -1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 3.0000 -3.4641 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 2.0000 -3.4641 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -3.4641 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 4.5000 -4.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0000 -3.4641 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.0000 -5.1962 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.5981 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -4.3301 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -1.7321 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0000 -3.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -4.3301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -0.0000 0.0000 O 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 4.5000 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -5.1962 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -6.0622 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -5.1962 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 5 1 0 0 0 0 2 6 1 0 0 0 0 3 4 1 0 0 0 0 3 11 1 0 0 0 0 4 17 1 0 0 0 0 5 18 2 0 0 0 0 6 19 2 0 0 0 0 7 10 2 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 31 1 0 0 0 0 12 19 1 0 0 0 0 12 21 2 0 0 0 0 13 23 1 0 0 0 0 14 29 1 0 0 0 0 15 17 1 0 0 0 0 15 31 1 0 0 0 0 16 24 1 0 0 0 0 16 32 1 0 0 0 0 17 14 1 1 0 0 0 18 19 1 0 0 0 0 20 32 1 0 0 0 0 21 39 1 0 0 0 0 22 13 1 1 0 0 0 22 25 1 0 0 0 0 22 30 1 0 0 0 0 23 29 2 3 0 0 0 23 33 1 0 0 0 0 24 34 2 0 0 0 0 24 35 1 0 0 0 0 25 32 1 0 0 0 0 25 36 2 0 0 0 0 26 27 2 0 0 0 0 26 28 1 0 0 0 0 26 31 1 0 0 0 0 27 40 1 0 0 0 0 28 41 1 0 0 0 0 28 42 1 0 0 0 0 30 39 1 0 0 0 0 30 43 1 0 0 0 0 33 44 1 0 0 0 0 35 45 1 0 0 0 0 37 39 2 0 0 0 0 38 39 2 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB007190
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	558.23
ALogP	-3.8406
MLogP	2.89
XLogP	1.309
HDA	12
HBD	5
Rotatable Bonds	16
TPSA	197.86
RO5 Violation	2