NPASS drugs

Drug Information

Drug ID:	NPD3982
Drug Name:	Maprotiline
Molecular Formula:	C20H23N
Canonical SMILES:	CNCCCC12CCC(c3c1cccc3)c1c2cccc1
Standard InCHI:	InChI=1S/C20H23N/c1-21-14-6-12-20-13-11-15(16-7-2-4-9-18(16)20)17-8-3-5-10-19(17)20/h2-5,7-10,15,21H,6,11-14H2,1H3
Standard InCHIKey:	QSLMDECMDJKHMQ-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD3982

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	321
0.1-0.2	1471
0.2-0.3	5725
0.3-0.4	15335
0.4-0.5	6706
0.5-0.6	1130
0.6-0.7	159
0.7-0.8	39
0.8-0.85	2
0.85-0.9	2
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	0.8876	NPC60408
High Similarity	0.8539	NPC133162
Intermediate Similarity	0.8041	NPC329430
Intermediate Similarity	0.8	NPC474582
Intermediate Similarity	0.7841	NPC139658
Intermediate Similarity	0.7778	NPC159661
Intermediate Similarity	0.7753	NPC249018
Intermediate Similarity	0.7753	NPC3190
Intermediate Similarity	0.7742	NPC169016
Intermediate Similarity	0.7692	NPC474695
Intermediate Similarity	0.7579	NPC258046
Intermediate Similarity	0.7573	NPC239854
Intermediate Similarity	0.7551	NPC470926
Intermediate Similarity	0.7528	NPC276699
Intermediate Similarity	0.75	NPC315216
Intermediate Similarity	0.7363	NPC290638
Intermediate Similarity	0.7303	NPC54269
Intermediate Similarity	0.7283	NPC245896
Intermediate Similarity	0.7283	NPC12857
Intermediate Similarity	0.7283	NPC66270
Intermediate Similarity	0.7273	NPC229235
Intermediate Similarity	0.7273	NPC72670
Intermediate Similarity	0.7263	NPC119677
Intermediate Similarity	0.7222	NPC112609
Intermediate Similarity	0.7222	NPC113000
Intermediate Similarity	0.7222	NPC122327
Intermediate Similarity	0.7143	NPC307195
Intermediate Similarity	0.713	NPC320656
Intermediate Similarity	0.7128	NPC50063
Intermediate Similarity	0.7083	NPC104070
Intermediate Similarity	0.708	NPC246904
Intermediate Similarity	0.7053	NPC231986
Intermediate Similarity	0.7033	NPC258492
Intermediate Similarity	0.7033	NPC96835
Intermediate Similarity	0.7018	NPC473573
Intermediate Similarity	0.7	NPC39799
Intermediate Similarity	0.7	NPC158028
Intermediate Similarity	0.7	NPC193578
Intermediate Similarity	0.7	NPC87099
Intermediate Similarity	0.7	NPC1008
Intermediate Similarity	0.7	NPC280135
Intermediate Similarity	0.7	NPC226999
Intermediate Similarity	0.7	NPC135433
Remote Similarity	0.6989	NPC325662
Remote Similarity	0.6989	NPC98269
Remote Similarity	0.6966	NPC246822
Remote Similarity	0.6966	NPC213570
Remote Similarity	0.6966	NPC139416
Remote Similarity	0.6897	NPC155172
Remote Similarity	0.6882	NPC271642
Remote Similarity	0.6855	NPC126458
Remote Similarity	0.6832	NPC298115
Remote Similarity	0.6829	NPC40488
Remote Similarity	0.6818	NPC178527
Remote Similarity	0.6803	NPC119326
Remote Similarity	0.6774	NPC98976
Remote Similarity	0.6742	NPC267443
Remote Similarity	0.6742	NPC6107
Remote Similarity	0.6737	NPC255345
Remote Similarity	0.6731	NPC469330
Remote Similarity	0.6705	NPC32312
Remote Similarity	0.6705	NPC291066
Remote Similarity	0.6705	NPC198023
Remote Similarity	0.6703	NPC251490
Remote Similarity	0.6703	NPC219246
Remote Similarity	0.6702	NPC110264
Remote Similarity	0.6699	NPC220596
Remote Similarity	0.6699	NPC125226
Remote Similarity	0.6667	NPC108339
Remote Similarity	0.6667	NPC29680
Remote Similarity	0.6667	NPC475915
Remote Similarity	0.6667	NPC71009
Remote Similarity	0.6667	NPC22786
Remote Similarity	0.6629	NPC289915
Remote Similarity	0.6629	NPC113837
Remote Similarity	0.6614	NPC149379
Remote Similarity	0.6612	NPC109151
Remote Similarity	0.6604	NPC471320
Remote Similarity	0.6604	NPC471319
Remote Similarity	0.6591	NPC113670
Remote Similarity	0.6591	NPC88566
Remote Similarity	0.6591	NPC45756
Remote Similarity	0.6571	NPC322040
Remote Similarity	0.6559	NPC244738
Remote Similarity	0.6559	NPC1901
Remote Similarity	0.6552	NPC246588
Remote Similarity	0.6552	NPC238023
Remote Similarity	0.6552	NPC135924
Remote Similarity	0.6552	NPC210849
Remote Similarity	0.6552	NPC310758
Remote Similarity	0.6535	NPC203076
Remote Similarity	0.6522	NPC263385
Remote Similarity	0.6462	NPC478140
Remote Similarity	0.646	NPC434
Remote Similarity	0.646	NPC79618
Remote Similarity	0.6452	NPC79698
Remote Similarity	0.6449	NPC185208
Remote Similarity	0.6449	NPC219573
Remote Similarity	0.6415	NPC7067
Remote Similarity	0.6413	NPC200936
Remote Similarity	0.6408	NPC30445
Remote Similarity	0.64	NPC252794
Remote Similarity	0.64	NPC474088
Remote Similarity	0.6393	NPC273830
Remote Similarity	0.6389	NPC324602
Remote Similarity	0.6364	NPC150196
Remote Similarity	0.6364	NPC476993
Remote Similarity	0.6364	NPC54368
Remote Similarity	0.6364	NPC248705
Remote Similarity	0.6346	NPC176858
Remote Similarity	0.6328	NPC89769
Remote Similarity	0.6328	NPC126859
Remote Similarity	0.6328	NPC259665
Remote Similarity	0.6322	NPC114327
Remote Similarity	0.6322	NPC36357
Remote Similarity	0.6321	NPC108800
Remote Similarity	0.63	NPC14326
Remote Similarity	0.6292	NPC66517
Remote Similarity	0.6286	NPC191444
Remote Similarity	0.6283	NPC167336
Remote Similarity	0.6283	NPC474559
Remote Similarity	0.6279	NPC473962
Remote Similarity	0.6273	NPC221825
Remote Similarity	0.625	NPC472691
Remote Similarity	0.625	NPC471829
Remote Similarity	0.625	NPC147062
Remote Similarity	0.625	NPC474866
Remote Similarity	0.625	NPC475939
Remote Similarity	0.6239	NPC239185
Remote Similarity	0.6237	NPC473206
Remote Similarity	0.6228	NPC473498
Remote Similarity	0.6222	NPC21211
Remote Similarity	0.6216	NPC133809
Remote Similarity	0.6216	NPC128248
Remote Similarity	0.6216	NPC136810
Remote Similarity	0.6207	NPC120441
Remote Similarity	0.6207	NPC65873
Remote Similarity	0.6207	NPC300345
Remote Similarity	0.6207	NPC212114
Remote Similarity	0.62	NPC242628
Remote Similarity	0.6195	NPC275467
Remote Similarity	0.6182	NPC134882
Remote Similarity	0.6168	NPC59677
Remote Similarity	0.6168	NPC323420
Remote Similarity	0.6162	NPC211322
Remote Similarity	0.6161	NPC327226
Remote Similarity	0.6161	NPC291610
Remote Similarity	0.6154	NPC473031
Remote Similarity	0.6154	NPC305602
Remote Similarity	0.6154	NPC17497
Remote Similarity	0.6148	NPC264580
Remote Similarity	0.6146	NPC299134
Remote Similarity	0.614	NPC473418
Remote Similarity	0.6136	NPC8235
Remote Similarity	0.6136	NPC64270
Remote Similarity	0.6132	NPC172128
Remote Similarity	0.6132	NPC26224
Remote Similarity	0.6124	NPC124802
Remote Similarity	0.6121	NPC77294
Remote Similarity	0.6111	NPC200745
Remote Similarity	0.6106	NPC19856
Remote Similarity	0.61	NPC12035
Remote Similarity	0.6095	NPC267262
Remote Similarity	0.6095	NPC12429
Remote Similarity	0.6094	NPC145754
Remote Similarity	0.6092	NPC269586
Remote Similarity	0.6092	NPC198841
Remote Similarity	0.6091	NPC311242
Remote Similarity	0.6091	NPC226041
Remote Similarity	0.6091	NPC265220
Remote Similarity	0.6075	NPC475023
Remote Similarity	0.6075	NPC475059
Remote Similarity	0.6071	NPC109514
Remote Similarity	0.6068	NPC292758
Remote Similarity	0.6068	NPC65855
Remote Similarity	0.6064	NPC297358
Remote Similarity	0.6061	NPC132847
Remote Similarity	0.6061	NPC325568
Remote Similarity	0.6055	NPC472880
Remote Similarity	0.6053	NPC56168
Remote Similarity	0.6053	NPC150254
Remote Similarity	0.6053	NPC226778
Remote Similarity	0.6053	NPC147000
Remote Similarity	0.6053	NPC304761
Remote Similarity	0.6047	NPC8305
Remote Similarity	0.6047	NPC268763
Remote Similarity	0.6047	NPC66177
Remote Similarity	0.6044	NPC50266
Remote Similarity	0.6042	NPC212463
Remote Similarity	0.6038	NPC470877
Remote Similarity	0.6036	NPC75724
Remote Similarity	0.6036	NPC49994
Remote Similarity	0.6019	NPC267704
Remote Similarity	0.6019	NPC475057
Remote Similarity	0.6019	NPC473661
Remote Similarity	0.6014	NPC311330
Remote Similarity	0.6	NPC316896
Remote Similarity	0.6	NPC71684
Remote Similarity	0.6	NPC314192
Remote Similarity	0.6	NPC67043

Drug Structure

NPD3982 OpenBabel08211704332D 22 25 0 0 1 0 0 0 0 0999 V2000 -1.9009 1.8287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6870 -1.5519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6876 -1.5513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6872 -0.5176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6875 -0.5170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6337 1.0973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7912 -2.0690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7919 -2.0686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7915 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7917 0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -1.4353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0001 0.7316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3659 -0.6335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6338 1.8289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 -2.0689 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8955 -1.5517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8961 -1.5515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8956 -0.5174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8960 -0.5172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.2674 2.1946 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.2675 2.9262 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 4 2 0 0 0 0 2 7 1 0 0 0 0 3 5 2 0 0 0 0 3 8 1 0 0 0 0 4 9 1 0 0 0 0 5 10 1 0 0 0 0 6 12 1 0 0 0 0 6 14 1 0 0 0 0 7 16 2 0 0 0 0 8 17 2 0 0 0 0 9 18 2 0 0 0 0 10 19 2 0 0 0 0 11 13 1 0 0 0 0 11 15 1 0 0 0 0 12 20 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 19 20 1 0 0 0 0 21 22 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP001150
DrugBank	DB00934
ChEMBL	CHEMBL21731
IUPHAR/BPS	2402
PharmaGKB	PA450322
KEGG Drug	D02566
PubChem CID	4011
ChEBI	6690
CAS Number	10262-69-8

Drug Properties

Molecular Weight	277.18
ALogP	-0.7148
MLogP	3.55
XLogP	8.576
HDA	1
HBD	1
Rotatable Bonds	5
TPSA	12.03
RO5 Violation	1