NPASS drugs

Drug Information

Drug ID:	NPD3149
Drug Name:	Bupivacaine
Molecular Formula:	C18H28N2O
Canonical SMILES:	CCCCN1CCCCC1C(=Nc1c(C)cccc1C)O
Standard InCHI:	InChI=1S/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21)
Standard InCHIKey:	LEBVLXFERQHONN-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD3149

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	130
0.1-0.2	1038
0.2-0.3	8117
0.3-0.4	12951
0.4-0.5	5779
0.5-0.6	2342
0.6-0.7	488
0.7-0.8	45
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	0.7669	NPC243162
Intermediate Similarity	0.7664	NPC78154
Intermediate Similarity	0.757	NPC470877
Intermediate Similarity	0.75	NPC78041
Intermediate Similarity	0.75	NPC471307
Intermediate Similarity	0.75	NPC74936
Intermediate Similarity	0.75	NPC159178
Intermediate Similarity	0.75	NPC209764
Intermediate Similarity	0.75	NPC141139
Intermediate Similarity	0.75	NPC121872
Intermediate Similarity	0.7391	NPC178681
Intermediate Similarity	0.7387	NPC303045
Intermediate Similarity	0.7387	NPC161972
Intermediate Similarity	0.7339	NPC264580
Intermediate Similarity	0.7323	NPC328683
Intermediate Similarity	0.7323	NPC283130
Intermediate Similarity	0.7321	NPC25565
Intermediate Similarity	0.7304	NPC291610
Intermediate Similarity	0.7297	NPC471309
Intermediate Similarity	0.7295	NPC205652
Intermediate Similarity	0.7273	NPC226438
Intermediate Similarity	0.7257	NPC473501
Intermediate Similarity	0.7257	NPC311242
Intermediate Similarity	0.7257	NPC475439
Intermediate Similarity	0.7231	NPC478079
Intermediate Similarity	0.7154	NPC33742
Intermediate Similarity	0.7154	NPC470550
Intermediate Similarity	0.7143	NPC476483
Intermediate Similarity	0.7121	NPC226662
Intermediate Similarity	0.7099	NPC476950
Intermediate Similarity	0.7092	NPC472100
Intermediate Similarity	0.7083	NPC164802
Intermediate Similarity	0.7073	NPC35850
Intermediate Similarity	0.7073	NPC276949
Intermediate Similarity	0.7071	NPC472103
Intermediate Similarity	0.7042	NPC254798
Intermediate Similarity	0.704	NPC147957
Intermediate Similarity	0.704	NPC470544
Intermediate Similarity	0.7037	NPC184437
Intermediate Similarity	0.7027	NPC316108
Intermediate Similarity	0.7021	NPC116519
Intermediate Similarity	0.7015	NPC476687
Intermediate Similarity	0.7015	NPC476689
Intermediate Similarity	0.7015	NPC476685
Intermediate Similarity	0.7009	NPC15839
Remote Similarity	0.6984	NPC192209
Remote Similarity	0.6984	NPC470545
Remote Similarity	0.6953	NPC316582
Remote Similarity	0.6939	NPC477156
Remote Similarity	0.6939	NPC477157
Remote Similarity	0.6935	NPC296163
Remote Similarity	0.6935	NPC187036
Remote Similarity	0.6929	NPC470546
Remote Similarity	0.6909	NPC471638
Remote Similarity	0.6909	NPC473031
Remote Similarity	0.6891	NPC224610
Remote Similarity	0.6891	NPC88267
Remote Similarity	0.6891	NPC113326
Remote Similarity	0.6891	NPC194390
Remote Similarity	0.6884	NPC122553
Remote Similarity	0.6875	NPC172128
Remote Similarity	0.686	NPC37584
Remote Similarity	0.685	NPC313449
Remote Similarity	0.6847	NPC12429
Remote Similarity	0.6822	NPC317564
Remote Similarity	0.6822	NPC307456
Remote Similarity	0.6818	NPC325013
Remote Similarity	0.6814	NPC470926
Remote Similarity	0.6807	NPC471310
Remote Similarity	0.6807	NPC202613
Remote Similarity	0.6807	NPC471317
Remote Similarity	0.6797	NPC228515
Remote Similarity	0.6788	NPC313352
Remote Similarity	0.6783	NPC58674
Remote Similarity	0.6772	NPC239357
Remote Similarity	0.6769	NPC71684
Remote Similarity	0.6757	NPC207726
Remote Similarity	0.6741	NPC314431
Remote Similarity	0.6736	NPC264589
Remote Similarity	0.6723	NPC239854
Remote Similarity	0.6696	NPC111233
Remote Similarity	0.6693	NPC288232
Remote Similarity	0.6692	NPC474926
Remote Similarity	0.6692	NPC476990
Remote Similarity	0.6689	NPC477158
Remote Similarity	0.6689	NPC68650
Remote Similarity	0.6667	NPC104345
Remote Similarity	0.6667	NPC211525
Remote Similarity	0.6667	NPC245259
Remote Similarity	0.6667	NPC129721
Remote Similarity	0.6667	NPC302790
Remote Similarity	0.6667	NPC153694
Remote Similarity	0.6667	NPC471313
Remote Similarity	0.6667	NPC471311
Remote Similarity	0.6644	NPC473297
Remote Similarity	0.6641	NPC14672
Remote Similarity	0.6641	NPC202521
Remote Similarity	0.6641	NPC285926
Remote Similarity	0.6641	NPC315276
Remote Similarity	0.6639	NPC214200
Remote Similarity	0.6639	NPC327481
Remote Similarity	0.6639	NPC228400
Remote Similarity	0.6623	NPC243673
Remote Similarity	0.6623	NPC310403
Remote Similarity	0.6623	NPC67056
Remote Similarity	0.6623	NPC263709
Remote Similarity	0.6623	NPC148468
Remote Similarity	0.6623	NPC63210
Remote Similarity	0.6623	NPC97380
Remote Similarity	0.662	NPC316202
Remote Similarity	0.6613	NPC292758
Remote Similarity	0.6613	NPC65855
Remote Similarity	0.6601	NPC194640
Remote Similarity	0.66	NPC84317
Remote Similarity	0.6599	NPC187951
Remote Similarity	0.6591	NPC252878
Remote Similarity	0.6569	NPC316746
Remote Similarity	0.6567	NPC101719
Remote Similarity	0.6565	NPC200964
Remote Similarity	0.656	NPC319579
Remote Similarity	0.6557	NPC211551
Remote Similarity	0.6555	NPC12730
Remote Similarity	0.6545	NPC104070
Remote Similarity	0.6544	NPC278451
Remote Similarity	0.6541	NPC46427
Remote Similarity	0.6541	NPC6975
Remote Similarity	0.6538	NPC81561
Remote Similarity	0.6536	NPC476231
Remote Similarity	0.6536	NPC133470
Remote Similarity	0.6536	NPC16667
Remote Similarity	0.6536	NPC191863
Remote Similarity	0.6536	NPC289776
Remote Similarity	0.6528	NPC314287
Remote Similarity	0.6525	NPC33168
Remote Similarity	0.6522	NPC325479
Remote Similarity	0.6518	NPC203076
Remote Similarity	0.6516	NPC278887
Remote Similarity	0.6515	NPC215519
Remote Similarity	0.6515	NPC475915
Remote Similarity	0.6513	NPC154478
Remote Similarity	0.6512	NPC313673
Remote Similarity	0.6509	NPC271642
Remote Similarity	0.6504	NPC474804
Remote Similarity	0.6504	NPC474973
Remote Similarity	0.6504	NPC130898
Remote Similarity	0.6503	NPC104483
Remote Similarity	0.6497	NPC158129
Remote Similarity	0.6494	NPC189116
Remote Similarity	0.6493	NPC222466
Remote Similarity	0.6493	NPC317758
Remote Similarity	0.6493	NPC22746
Remote Similarity	0.649	NPC285469
Remote Similarity	0.648	NPC470127
Remote Similarity	0.6475	NPC324611
Remote Similarity	0.6474	NPC469462
Remote Similarity	0.6462	NPC148140
Remote Similarity	0.6458	NPC477155
Remote Similarity	0.6457	NPC474584
Remote Similarity	0.6452	NPC470508
Remote Similarity	0.6452	NPC52059
Remote Similarity	0.6452	NPC470069
Remote Similarity	0.6444	NPC122718
Remote Similarity	0.6443	NPC475763
Remote Similarity	0.6441	NPC471320
Remote Similarity	0.6441	NPC471319
Remote Similarity	0.6429	NPC472121
Remote Similarity	0.6424	NPC38736
Remote Similarity	0.6424	NPC161827
Remote Similarity	0.6423	NPC101372
Remote Similarity	0.6423	NPC150863
Remote Similarity	0.6423	NPC469666
Remote Similarity	0.6423	NPC473322
Remote Similarity	0.6423	NPC259098
Remote Similarity	0.6423	NPC111428
Remote Similarity	0.6423	NPC197680
Remote Similarity	0.6423	NPC143516
Remote Similarity	0.6415	NPC329688
Remote Similarity	0.6415	NPC98976
Remote Similarity	0.6415	NPC189812
Remote Similarity	0.6412	NPC220698
Remote Similarity	0.641	NPC469330
Remote Similarity	0.6408	NPC287358
Remote Similarity	0.6404	NPC325441
Remote Similarity	0.6398	NPC133261
Remote Similarity	0.6395	NPC478039
Remote Similarity	0.6393	NPC164859
Remote Similarity	0.6392	NPC355
Remote Similarity	0.6387	NPC472258
Remote Similarity	0.6377	NPC9856
Remote Similarity	0.6376	NPC37548
Remote Similarity	0.6375	NPC203754
Remote Similarity	0.6375	NPC150048
Remote Similarity	0.6375	NPC134586
Remote Similarity	0.637	NPC311330
Remote Similarity	0.6369	NPC317430
Remote Similarity	0.6364	NPC255229
Remote Similarity	0.6364	NPC251722
Remote Similarity	0.6364	NPC177684
Remote Similarity	0.6364	NPC81229
Remote Similarity	0.6364	NPC231986

Drug Structure

NPD3149 OpenBabel08211702562D 22 23 0 0 1 0 0 0 0 0999 V2000 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 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 1 4 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 5 1 0 0 0 0 5 12 1 0 0 0 0 6 7 1 0 0 0 0 6 11 1 0 0 0 0 7 13 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 11 16 1 0 0 0 0 12 20 1 0 0 0 0 13 20 1 0 0 0 0 14 17 2 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 18 19 2 3 0 0 0 18 21 1 0 0 0 0 21 22 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP001229
DrugBank	DB00297
ChEMBL	CHEMBL1098
IUPHAR/BPS	2397
PharmaGKB	PA135057240
KEGG Drug
PubChem CID	2474
ChEBI	77431
CAS Number	38396-39-3

Drug Properties

Molecular Weight	288.22
ALogP	-0.307
MLogP	3.11
XLogP	4.906
HDA	3
HBD	1
Rotatable Bonds	9
TPSA	35.83
RO5 Violation	0