NPASS drugs

Drug Information

Drug ID:	NPD2374
Drug Name:	Amoxapine
Molecular Formula:	C17H16ClN3O
Canonical SMILES:	Clc1ccc2c(c1)C(=Nc1c(O2)cccc1)N1CCNCC1
Standard InCHI:	InChI=1S/C17H16ClN3O/c18-12-5-6-15-13(11-12)17(21-9-7-19-8-10-21)20-14-3-1-2-4-16(14)22-15/h1-6,11,19H,7-10H2
Standard InCHIKey:	QWGDMFLQWFTERH-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD2374

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	458
0.1-0.2	3776
0.2-0.3	9010
0.3-0.4	5470
0.4-0.5	10077
0.5-0.6	2043
0.6-0.7	55
0.7-0.8	1
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	0.7047	NPC232872
Remote Similarity	0.6667	NPC473432
Remote Similarity	0.6595	NPC315257
Remote Similarity	0.6492	NPC208280
Remote Similarity	0.6489	NPC306366
Remote Similarity	0.6474	NPC204179
Remote Similarity	0.6284	NPC473874
Remote Similarity	0.6256	NPC18890
Remote Similarity	0.6229	NPC56271
Remote Similarity	0.6229	NPC471321
Remote Similarity	0.6229	NPC471306
Remote Similarity	0.6226	NPC473422
Remote Similarity	0.6219	NPC469829
Remote Similarity	0.6215	NPC208022
Remote Similarity	0.6211	NPC26850
Remote Similarity	0.62	NPC118776
Remote Similarity	0.6195	NPC475411
Remote Similarity	0.6195	NPC92803
Remote Similarity	0.6178	NPC187145
Remote Similarity	0.617	NPC13397
Remote Similarity	0.6166	NPC118511
Remote Similarity	0.6161	NPC214368
Remote Similarity	0.6138	NPC26872
Remote Similarity	0.6127	NPC255253
Remote Similarity	0.6124	NPC314948
Remote Similarity	0.6124	NPC478049
Remote Similarity	0.6114	NPC329747
Remote Similarity	0.6114	NPC177404
Remote Similarity	0.6106	NPC198401
Remote Similarity	0.6106	NPC257851
Remote Similarity	0.6089	NPC98197
Remote Similarity	0.6085	NPC470586
Remote Similarity	0.607	NPC70092
Remote Similarity	0.6066	NPC189724
Remote Similarity	0.6066	NPC212850
Remote Similarity	0.6066	NPC314113
Remote Similarity	0.6066	NPC83289
Remote Similarity	0.6053	NPC471132
Remote Similarity	0.6052	NPC471614
Remote Similarity	0.6044	NPC476475
Remote Similarity	0.6038	NPC19872
Remote Similarity	0.6034	NPC328267
Remote Similarity	0.6022	NPC237227
Remote Similarity	0.6022	NPC325599
Remote Similarity	0.6022	NPC247298
Remote Similarity	0.602	NPC314861
Remote Similarity	0.602	NPC127362
Remote Similarity	0.6019	NPC194699
Remote Similarity	0.6019	NPC295287
Remote Similarity	0.6019	NPC219350
Remote Similarity	0.6019	NPC110741
Remote Similarity	0.601	NPC469831
Remote Similarity	0.6009	NPC111492
Remote Similarity	0.6	NPC297584
Remote Similarity	0.6	NPC70259
Remote Similarity	0.6	NPC184437
Remote Similarity	0.5981	NPC311357
Remote Similarity	0.5979	NPC231862
Remote Similarity	0.5978	NPC476687
Remote Similarity	0.5978	NPC476689
Remote Similarity	0.5978	NPC476685
Remote Similarity	0.5971	NPC469830
Remote Similarity	0.5967	NPC29650
Remote Similarity	0.5962	NPC329793
Remote Similarity	0.5962	NPC315957
Remote Similarity	0.596	NPC477888
Remote Similarity	0.5957	NPC245974
Remote Similarity	0.5953	NPC245816
Remote Similarity	0.5953	NPC473460
Remote Similarity	0.5953	NPC476138
Remote Similarity	0.5952	NPC205934
Remote Similarity	0.5952	NPC43787
Remote Similarity	0.5949	NPC133470
Remote Similarity	0.5949	NPC289776
Remote Similarity	0.5949	NPC57105
Remote Similarity	0.5949	NPC191863
Remote Similarity	0.5943	NPC315632
Remote Similarity	0.5943	NPC217277
Remote Similarity	0.5943	NPC72211
Remote Similarity	0.5942	NPC217294
Remote Similarity	0.5941	NPC316161
Remote Similarity	0.5939	NPC238430
Remote Similarity	0.5934	NPC138365
Remote Similarity	0.5931	NPC471785
Remote Similarity	0.5931	NPC314659
Remote Similarity	0.593	NPC85482
Remote Similarity	0.5928	NPC476287
Remote Similarity	0.5926	NPC470930
Remote Similarity	0.5926	NPC321617
Remote Similarity	0.5916	NPC47672
Remote Similarity	0.5913	NPC471593
Remote Similarity	0.5909	NPC1527
Remote Similarity	0.5909	NPC277306
Remote Similarity	0.5909	NPC469442
Remote Similarity	0.5907	NPC233926
Remote Similarity	0.5907	NPC477564
Remote Similarity	0.5907	NPC52801
Remote Similarity	0.5907	NPC2295
Remote Similarity	0.5904	NPC9373
Remote Similarity	0.59	NPC73280
Remote Similarity	0.5896	NPC317564
Remote Similarity	0.5891	NPC283152
Remote Similarity	0.5887	NPC475253
Remote Similarity	0.5886	NPC151237
Remote Similarity	0.5882	NPC197335
Remote Similarity	0.5882	NPC94157
Remote Similarity	0.5882	NPC228206
Remote Similarity	0.5876	NPC141739
Remote Similarity	0.5876	NPC136112
Remote Similarity	0.5874	NPC148183
Remote Similarity	0.5874	NPC152768
Remote Similarity	0.5871	NPC312872
Remote Similarity	0.587	NPC318591
Remote Similarity	0.587	NPC231163
Remote Similarity	0.587	NPC471762
Remote Similarity	0.5867	NPC471177
Remote Similarity	0.5867	NPC22014
Remote Similarity	0.5867	NPC88970
Remote Similarity	0.5867	NPC124542
Remote Similarity	0.5867	NPC59779
Remote Similarity	0.5866	NPC226662
Remote Similarity	0.5865	NPC242928
Remote Similarity	0.586	NPC267423
Remote Similarity	0.586	NPC476044
Remote Similarity	0.5859	NPC475393
Remote Similarity	0.5857	NPC79213
Remote Similarity	0.5856	NPC97870
Remote Similarity	0.5856	NPC247018
Remote Similarity	0.5856	NPC471953
Remote Similarity	0.5856	NPC469592
Remote Similarity	0.5856	NPC307123
Remote Similarity	0.5856	NPC478074
Remote Similarity	0.5856	NPC25539
Remote Similarity	0.5856	NPC471080
Remote Similarity	0.5853	NPC285558
Remote Similarity	0.5846	NPC301163
Remote Similarity	0.5846	NPC29647
Remote Similarity	0.5845	NPC475910
Remote Similarity	0.5842	NPC288943
Remote Similarity	0.5842	NPC8467
Remote Similarity	0.5838	NPC43275
Remote Similarity	0.5837	NPC471532
Remote Similarity	0.5833	NPC475112
Remote Similarity	0.5833	NPC475085
Remote Similarity	0.5833	NPC291535
Remote Similarity	0.583	NPC316297
Remote Similarity	0.583	NPC314817
Remote Similarity	0.583	NPC66191
Remote Similarity	0.5829	NPC475190
Remote Similarity	0.5826	NPC157931
Remote Similarity	0.5825	NPC84478
Remote Similarity	0.5822	NPC267928
Remote Similarity	0.5816	NPC79328
Remote Similarity	0.5814	NPC121772
Remote Similarity	0.5813	NPC285941
Remote Similarity	0.5811	NPC26679
Remote Similarity	0.581	NPC92111
Remote Similarity	0.5808	NPC471130
Remote Similarity	0.5808	NPC471178
Remote Similarity	0.5808	NPC254700
Remote Similarity	0.5806	NPC162484
Remote Similarity	0.5805	NPC263835
Remote Similarity	0.5805	NPC270301
Remote Similarity	0.5805	NPC474798
Remote Similarity	0.5803	NPC476568
Remote Similarity	0.5801	NPC66777
Remote Similarity	0.58	NPC151030
Remote Similarity	0.58	NPC269383
Remote Similarity	0.5797	NPC313886
Remote Similarity	0.5797	NPC42591
Remote Similarity	0.5797	NPC473007
Remote Similarity	0.5795	NPC93593
Remote Similarity	0.5795	NPC471315
Remote Similarity	0.5795	NPC471314
Remote Similarity	0.5792	NPC471304
Remote Similarity	0.5792	NPC167860
Remote Similarity	0.5792	NPC123976
Remote Similarity	0.5787	NPC232727
Remote Similarity	0.5787	NPC7393
Remote Similarity	0.5785	NPC162530
Remote Similarity	0.5781	NPC60538
Remote Similarity	0.5781	NPC207824
Remote Similarity	0.5777	NPC475479
Remote Similarity	0.5777	NPC176127
Remote Similarity	0.5777	NPC243454
Remote Similarity	0.5775	NPC13880
Remote Similarity	0.5771	NPC471648
Remote Similarity	0.5771	NPC472099
Remote Similarity	0.5769	NPC87391
Remote Similarity	0.5769	NPC274732
Remote Similarity	0.5767	NPC18487
Remote Similarity	0.5765	NPC170503
Remote Similarity	0.5765	NPC126519
Remote Similarity	0.5765	NPC203784
Remote Similarity	0.5765	NPC26524
Remote Similarity	0.5762	NPC76748
Remote Similarity	0.5759	NPC476151
Remote Similarity	0.5759	NPC106295
Remote Similarity	0.5759	NPC16107
Remote Similarity	0.5759	NPC51957

Drug Structure

NPD2374 OpenBabel08211702172D 23 26 0 0 0 0 0 0 0 0999 V2000 2.4283 0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9916 0.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4311 0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5577 -0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5311 -3.7219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3349 -3.2219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8138 0.8314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3244 -0.8237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8583 0.5366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3688 -1.1185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3972 -2.2219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3972 -3.2219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5311 -1.7219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9972 -0.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3349 -2.2219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5605 -0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6802 -0.7331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2632 -3.7219 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -3.5469 0.1512 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 -1.6357 -0.4383 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2658 -1.8565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5025 0.4460 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 14 2 0 0 0 0 4 16 2 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 15 1 0 0 0 0 7 9 1 0 0 0 0 7 19 1 0 0 0 0 8 10 1 0 0 0 0 8 19 1 0 0 0 0 9 21 1 0 0 0 0 10 21 1 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 12 18 1 0 0 0 0 13 15 2 0 0 0 0 13 17 1 0 0 0 0 14 16 1 0 0 0 0 14 20 1 0 0 0 0 15 22 1 0 0 0 0 16 22 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP001149
DrugBank	DB00543
ChEMBL	CHEMBL1113
IUPHAR/BPS	201
PharmaGKB	PA448405
KEGG Drug	D00228
PubChem CID	2170
ChEBI	2675
CAS Number	14028-44-5

Drug Properties

Molecular Weight	313.10
ALogP	-0.2604
MLogP	2.78
XLogP	4.069
HDA	3
HBD	1
Rotatable Bonds	2
TPSA	36.86
RO5 Violation	0