NPASS drugs

Drug Information

Drug ID:	NPD5181
Drug Name:	Fentanyl
Molecular Formula:	C22H28N2O
Canonical SMILES:	CCC(=O)N(c1ccccc1)C1CCN(CC1)CCc1ccccc1
Standard InCHI:	InChI=1S/C22H28N2O/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19/h3-12,21H,2,13-18H2,1H3
Standard InCHIKey:	PJMPHNIQZUBGLI-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD5181

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	157
0.1-0.2	1838
0.2-0.3	9930
0.3-0.4	12217
0.4-0.5	4424
0.5-0.6	1867
0.6-0.7	400
0.7-0.8	56
0.8-0.85	0
0.85-0.9	1
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	0.8952	NPC291610
Intermediate Similarity	0.7744	NPC186284
Intermediate Similarity	0.7744	NPC22082
Intermediate Similarity	0.7719	NPC473418
Intermediate Similarity	0.7705	NPC226143
Intermediate Similarity	0.7669	NPC130251
Intermediate Similarity	0.7594	NPC469560
Intermediate Similarity	0.7581	NPC257490
Intermediate Similarity	0.7576	NPC471123
Intermediate Similarity	0.75	NPC316582
Intermediate Similarity	0.748	NPC228515
Intermediate Similarity	0.744	NPC475915
Intermediate Similarity	0.7434	NPC75496
Intermediate Similarity	0.7431	NPC470926
Intermediate Similarity	0.7419	NPC177684
Intermediate Similarity	0.7419	NPC291962
Intermediate Similarity	0.7398	NPC313449
Intermediate Similarity	0.7368	NPC300299
Intermediate Similarity	0.736	NPC161956
Intermediate Similarity	0.736	NPC112373
Intermediate Similarity	0.736	NPC258531
Intermediate Similarity	0.7357	NPC109787
Intermediate Similarity	0.7355	NPC187036
Intermediate Similarity	0.7353	NPC301760
Intermediate Similarity	0.7313	NPC325599
Intermediate Similarity	0.7293	NPC316104
Intermediate Similarity	0.7293	NPC162417
Intermediate Similarity	0.7258	NPC192209
Intermediate Similarity	0.7254	NPC66936
Intermediate Similarity	0.7246	NPC469537
Intermediate Similarity	0.7236	NPC288232
Intermediate Similarity	0.7231	NPC476950
Intermediate Similarity	0.7227	NPC302790
Intermediate Similarity	0.7222	NPC17497
Intermediate Similarity	0.7222	NPC305602
Intermediate Similarity	0.7217	NPC326792
Intermediate Similarity	0.7213	NPC296163
Intermediate Similarity	0.7203	NPC117032
Intermediate Similarity	0.7154	NPC252794
Intermediate Similarity	0.7143	NPC53044
Intermediate Similarity	0.7143	NPC20322
Intermediate Similarity	0.7133	NPC154602
Intermediate Similarity	0.7133	NPC243756
Intermediate Similarity	0.7109	NPC268534
Intermediate Similarity	0.7101	NPC470301
Intermediate Similarity	0.708	NPC83214
Intermediate Similarity	0.7075	NPC276085
Intermediate Similarity	0.7073	NPC57051
Intermediate Similarity	0.7068	NPC231382
Intermediate Similarity	0.7063	NPC264580
Intermediate Similarity	0.7063	NPC220698
Intermediate Similarity	0.7059	NPC267508
Intermediate Similarity	0.7023	NPC250476
Intermediate Similarity	0.7007	NPC222029
Intermediate Similarity	0.7007	NPC113946
Intermediate Similarity	0.7	NPC434
Intermediate Similarity	0.7	NPC79618
Remote Similarity	0.6992	NPC473417
Remote Similarity	0.697	NPC478079
Remote Similarity	0.6957	NPC472258
Remote Similarity	0.6957	NPC65408
Remote Similarity	0.6953	NPC179605
Remote Similarity	0.6953	NPC279385
Remote Similarity	0.6944	NPC473329
Remote Similarity	0.693	NPC329430
Remote Similarity	0.6923	NPC212799
Remote Similarity	0.6912	NPC313352
Remote Similarity	0.6908	NPC63047
Remote Similarity	0.6908	NPC475248
Remote Similarity	0.6906	NPC315051
Remote Similarity	0.6903	NPC473661
Remote Similarity	0.6899	NPC103292
Remote Similarity	0.6879	NPC308197
Remote Similarity	0.687	NPC192533
Remote Similarity	0.6867	NPC472117
Remote Similarity	0.6867	NPC472101
Remote Similarity	0.6867	NPC472120
Remote Similarity	0.6866	NPC187231
Remote Similarity	0.6864	NPC239854
Remote Similarity	0.6857	NPC471164
Remote Similarity	0.6853	NPC470440
Remote Similarity	0.6852	NPC104070
Remote Similarity	0.6849	NPC285381
Remote Similarity	0.6849	NPC122106
Remote Similarity	0.6846	NPC39818
Remote Similarity	0.6833	NPC167336
Remote Similarity	0.6824	NPC29285
Remote Similarity	0.6818	NPC470343
Remote Similarity	0.6818	NPC472244
Remote Similarity	0.6809	NPC238499
Remote Similarity	0.6806	NPC254798
Remote Similarity	0.68	NPC472102
Remote Similarity	0.68	NPC309531
Remote Similarity	0.68	NPC225319
Remote Similarity	0.6791	NPC150863
Remote Similarity	0.6786	NPC207554
Remote Similarity	0.6779	NPC104345
Remote Similarity	0.6777	NPC473498
Remote Similarity	0.6777	NPC45033
Remote Similarity	0.6776	NPC472106
Remote Similarity	0.6769	NPC314192
Remote Similarity	0.6765	NPC207428
Remote Similarity	0.6755	NPC194881
Remote Similarity	0.675	NPC275467
Remote Similarity	0.6741	NPC314431
Remote Similarity	0.6741	NPC280807
Remote Similarity	0.6741	NPC472245
Remote Similarity	0.6738	NPC471574
Remote Similarity	0.6738	NPC2823
Remote Similarity	0.6736	NPC264589
Remote Similarity	0.6732	NPC279527
Remote Similarity	0.6732	NPC214960
Remote Similarity	0.6727	NPC229477
Remote Similarity	0.6726	NPC78154
Remote Similarity	0.6726	NPC191444
Remote Similarity	0.6716	NPC145754
Remote Similarity	0.6711	NPC469536
Remote Similarity	0.6692	NPC79698
Remote Similarity	0.6667	NPC209389
Remote Similarity	0.6667	NPC474430
Remote Similarity	0.6667	NPC242269
Remote Similarity	0.6667	NPC271642
Remote Similarity	0.6667	NPC164802
Remote Similarity	0.6667	NPC473743
Remote Similarity	0.6645	NPC469741
Remote Similarity	0.6644	NPC242000
Remote Similarity	0.6642	NPC322433
Remote Similarity	0.6641	NPC313673
Remote Similarity	0.6641	NPC470544
Remote Similarity	0.6638	NPC256452
Remote Similarity	0.6637	NPC176858
Remote Similarity	0.6636	NPC169016
Remote Similarity	0.6623	NPC471122
Remote Similarity	0.6618	NPC9856
Remote Similarity	0.6614	NPC246904
Remote Similarity	0.6597	NPC136002
Remote Similarity	0.6596	NPC314102
Remote Similarity	0.6596	NPC251722
Remote Similarity	0.6589	NPC31651
Remote Similarity	0.6589	NPC470545
Remote Similarity	0.6577	NPC478076
Remote Similarity	0.6571	NPC98976
Remote Similarity	0.6562	NPC473573
Remote Similarity	0.6562	NPC286994
Remote Similarity	0.6561	NPC96901
Remote Similarity	0.6561	NPC251212
Remote Similarity	0.6561	NPC139085
Remote Similarity	0.6561	NPC214626
Remote Similarity	0.6561	NPC161861
Remote Similarity	0.6558	NPC471124
Remote Similarity	0.6556	NPC61013
Remote Similarity	0.6547	NPC184437
Remote Similarity	0.6545	NPC474088
Remote Similarity	0.6545	NPC134825
Remote Similarity	0.6541	NPC254698
Remote Similarity	0.6538	NPC470546
Remote Similarity	0.6538	NPC81561
Remote Similarity	0.6536	NPC282339
Remote Similarity	0.6536	NPC176983
Remote Similarity	0.6536	NPC99632
Remote Similarity	0.6525	NPC287358
Remote Similarity	0.6525	NPC122553
Remote Similarity	0.6513	NPC193410
Remote Similarity	0.6513	NPC36495
Remote Similarity	0.6507	NPC469735
Remote Similarity	0.6503	NPC104483
Remote Similarity	0.6497	NPC355
Remote Similarity	0.6494	NPC478182
Remote Similarity	0.6489	NPC162689
Remote Similarity	0.6489	NPC54102
Remote Similarity	0.6484	NPC33742
Remote Similarity	0.6474	NPC33507
Remote Similarity	0.6471	NPC68650
Remote Similarity	0.6471	NPC248117
Remote Similarity	0.6467	NPC281094
Remote Similarity	0.6466	NPC48564
Remote Similarity	0.6466	NPC108800
Remote Similarity	0.6466	NPC182570
Remote Similarity	0.6466	NPC265605
Remote Similarity	0.6463	NPC469740
Remote Similarity	0.6463	NPC478186
Remote Similarity	0.6462	NPC148140
Remote Similarity	0.646	NPC262295
Remote Similarity	0.6449	NPC126458
Remote Similarity	0.6447	NPC477887
Remote Similarity	0.6444	NPC122718
Remote Similarity	0.6438	NPC28848
Remote Similarity	0.6438	NPC14325
Remote Similarity	0.6434	NPC243162
Remote Similarity	0.6423	NPC474695
Remote Similarity	0.6415	NPC470548
Remote Similarity	0.6414	NPC277157
Remote Similarity	0.6414	NPC473868
Remote Similarity	0.6414	NPC63157
Remote Similarity	0.641	NPC71140
Remote Similarity	0.641	NPC474974
Remote Similarity	0.6406	NPC276949
Remote Similarity	0.6406	NPC35850
Remote Similarity	0.6404	NPC30445
Remote Similarity	0.6403	NPC473962

Drug Structure

NPD5181 OpenBabel08211706322D 25 27 0 0 0 0 0 0 0 0999 V2000 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 -3.4641 2.0000 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 5.1962 -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 -2.5981 1.5000 0.0000 C 0 0 0 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 4.3301 -1.5000 0.0000 C 0 0 0 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 0.8660 -1.5000 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 -0.8660 0.5000 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 -2.5981 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 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 2.5981 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 22 1 0 0 0 0 3 5 2 0 0 0 0 3 6 1 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 19 2 0 0 0 0 10 19 1 0 0 0 0 11 20 2 0 0 0 0 12 20 1 0 0 0 0 13 16 1 0 0 0 0 13 19 1 0 0 0 0 14 17 1 0 0 0 0 14 21 1 0 0 0 0 15 18 1 0 0 0 0 15 21 1 0 0 0 0 16 23 1 0 0 0 0 17 23 1 0 0 0 0 18 23 1 0 0 0 0 20 24 1 0 0 0 0 21 24 1 0 0 0 0 22 24 1 0 0 0 0 22 25 2 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB009912; DAP000072
DrugBank	DB00813
ChEMBL	CHEMBL596
IUPHAR/BPS	1626
PharmaGKB	PA449599
KEGG Drug	D00320
PubChem CID	159600
ChEBI	119915
CAS Number	437-38-7

Drug Properties

Molecular Weight	336.22
ALogP	-0.8715
MLogP	3.55
XLogP	6.732
HDA	3
HBD	0
Rotatable Bonds	8
TPSA	23.55
RO5 Violation	1