NPASS drugs

Drug Information

Drug ID:	NPD3303
Drug Name:	CEE-03-320
Molecular Formula:	C19H18Cl3NO2
Canonical SMILES:	CN1CCc2c([C@H](C1)c1c(Cl)c(Cl)cc3c1OCC3)cc(c(c2)Cl)O
Standard InCHI:	InChI=1S/C19H18Cl3NO2/c1-23-4-2-10-6-14(20)16(24)8-12(10)13(9-23)17-18(22)15(21)7-11-3-5-25-19(11)17/h6-8,13,24H,2-5,9H2,1H3/t13-/m0/s1
Standard InCHIKey:	XTBPVXNRDRWQNN-ZDUSSCGKSA-N
Max Developmental Stage:	Discontinued
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD3303

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	275
0.1-0.2	1505
0.2-0.3	5784
0.3-0.4	8036
0.4-0.5	6075
0.5-0.6	8421
0.6-0.7	783
0.7-0.8	11
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	0.7287	NPC474498
Intermediate Similarity	0.7229	NPC139335
Intermediate Similarity	0.7152	NPC246991
Intermediate Similarity	0.7073	NPC8058
Intermediate Similarity	0.7033	NPC18402
Intermediate Similarity	0.7017	NPC148014
Intermediate Similarity	0.7017	NPC65490
Intermediate Similarity	0.7017	NPC40389
Intermediate Similarity	0.7017	NPC78359
Intermediate Similarity	0.7017	NPC129603
Intermediate Similarity	0.7017	NPC315707
Remote Similarity	0.6936	NPC252901
Remote Similarity	0.6875	NPC45072
Remote Similarity	0.6868	NPC56379
Remote Similarity	0.6864	NPC193334
Remote Similarity	0.6798	NPC476151
Remote Similarity	0.6791	NPC124657
Remote Similarity	0.6774	NPC124433
Remote Similarity	0.6774	NPC293871
Remote Similarity	0.6734	NPC264938
Remote Similarity	0.6722	NPC477565
Remote Similarity	0.6722	NPC103379
Remote Similarity	0.6705	NPC131379
Remote Similarity	0.6685	NPC185838
Remote Similarity	0.6667	NPC475557
Remote Similarity	0.6667	NPC42644
Remote Similarity	0.6646	NPC321133
Remote Similarity	0.6632	NPC204908
Remote Similarity	0.6632	NPC83198
Remote Similarity	0.6627	NPC150026
Remote Similarity	0.6611	NPC191376
Remote Similarity	0.6611	NPC179825
Remote Similarity	0.6611	NPC321505
Remote Similarity	0.6595	NPC180756
Remote Similarity	0.6595	NPC323443
Remote Similarity	0.6592	NPC145304
Remote Similarity	0.6579	NPC298979
Remote Similarity	0.6578	NPC166014
Remote Similarity	0.6578	NPC27410
Remote Similarity	0.6575	NPC135538
Remote Similarity	0.6575	NPC476571
Remote Similarity	0.6575	NPC428
Remote Similarity	0.6575	NPC24233
Remote Similarity	0.6575	NPC147390
Remote Similarity	0.6575	NPC246587
Remote Similarity	0.6571	NPC193528
Remote Similarity	0.6566	NPC14287
Remote Similarity	0.6561	NPC134858
Remote Similarity	0.655	NPC185313
Remote Similarity	0.655	NPC474499
Remote Similarity	0.6548	NPC33402
Remote Similarity	0.6543	NPC60186
Remote Similarity	0.6541	NPC127674
Remote Similarity	0.6541	NPC172765
Remote Similarity	0.6541	NPC276588
Remote Similarity	0.6541	NPC54379
Remote Similarity	0.6541	NPC469817
Remote Similarity	0.6541	NPC193949
Remote Similarity	0.6541	NPC39701
Remote Similarity	0.6541	NPC295691
Remote Similarity	0.6541	NPC5238
Remote Similarity	0.6541	NPC204828
Remote Similarity	0.6541	NPC278799
Remote Similarity	0.6541	NPC207757
Remote Similarity	0.6541	NPC110416
Remote Similarity	0.6541	NPC249797
Remote Similarity	0.6541	NPC2413
Remote Similarity	0.6541	NPC189266
Remote Similarity	0.6541	NPC184026
Remote Similarity	0.6528	NPC152680
Remote Similarity	0.6528	NPC190783
Remote Similarity	0.6528	NPC232386
Remote Similarity	0.6524	NPC221864
Remote Similarity	0.6522	NPC26601
Remote Similarity	0.6517	NPC471803
Remote Similarity	0.6514	NPC131204
Remote Similarity	0.6514	NPC301050
Remote Similarity	0.6509	NPC81641
Remote Similarity	0.6508	NPC324144
Remote Similarity	0.6508	NPC233650
Remote Similarity	0.6508	NPC1229
Remote Similarity	0.6505	NPC186063
Remote Similarity	0.6503	NPC97221
Remote Similarity	0.6503	NPC88249
Remote Similarity	0.6503	NPC151895
Remote Similarity	0.6503	NPC220858
Remote Similarity	0.6503	NPC192768
Remote Similarity	0.6497	NPC302449
Remote Similarity	0.6492	NPC210140
Remote Similarity	0.6489	NPC249274
Remote Similarity	0.6489	NPC271388
Remote Similarity	0.6489	NPC205167
Remote Similarity	0.6489	NPC205255
Remote Similarity	0.6489	NPC230956
Remote Similarity	0.6489	NPC235143
Remote Similarity	0.6489	NPC119649
Remote Similarity	0.6488	NPC255253
Remote Similarity	0.6486	NPC477564
Remote Similarity	0.6486	NPC2295
Remote Similarity	0.6485	NPC322424
Remote Similarity	0.6474	NPC78222
Remote Similarity	0.6474	NPC238530
Remote Similarity	0.6474	NPC477563
Remote Similarity	0.6474	NPC196447
Remote Similarity	0.6474	NPC13504
Remote Similarity	0.6474	NPC96603
Remote Similarity	0.6474	NPC276944
Remote Similarity	0.6474	NPC253043
Remote Similarity	0.6474	NPC212794
Remote Similarity	0.6474	NPC232514
Remote Similarity	0.6474	NPC136508
Remote Similarity	0.6474	NPC306843
Remote Similarity	0.6471	NPC79328
Remote Similarity	0.6464	NPC473934
Remote Similarity	0.6455	NPC80759
Remote Similarity	0.6455	NPC79402
Remote Similarity	0.6453	NPC471806
Remote Similarity	0.6453	NPC471810
Remote Similarity	0.6453	NPC471807
Remote Similarity	0.6448	NPC207824
Remote Similarity	0.6448	NPC211296
Remote Similarity	0.6448	NPC60538
Remote Similarity	0.6447	NPC305847
Remote Similarity	0.6446	NPC67791
Remote Similarity	0.6436	NPC111485
Remote Similarity	0.6432	NPC133011
Remote Similarity	0.6432	NPC82285
Remote Similarity	0.6418	NPC206900
Remote Similarity	0.6417	NPC147091
Remote Similarity	0.6416	NPC196193
Remote Similarity	0.6413	NPC274026
Remote Similarity	0.641	NPC199465
Remote Similarity	0.641	NPC128560
Remote Similarity	0.641	NPC229166
Remote Similarity	0.6407	NPC129176
Remote Similarity	0.6406	NPC12053
Remote Similarity	0.6406	NPC117188
Remote Similarity	0.6406	NPC81218
Remote Similarity	0.6406	NPC145832
Remote Similarity	0.6406	NPC205421
Remote Similarity	0.6406	NPC474931
Remote Similarity	0.6406	NPC150879
Remote Similarity	0.6406	NPC158376
Remote Similarity	0.6406	NPC306555
Remote Similarity	0.6406	NPC284842
Remote Similarity	0.6404	NPC471805
Remote Similarity	0.6404	NPC121100
Remote Similarity	0.6404	NPC314682
Remote Similarity	0.6404	NPC471813
Remote Similarity	0.6402	NPC165797
Remote Similarity	0.6402	NPC4304
Remote Similarity	0.6395	NPC283079
Remote Similarity	0.6393	NPC7467
Remote Similarity	0.639	NPC214901
Remote Similarity	0.6378	NPC76213
Remote Similarity	0.6378	NPC81733
Remote Similarity	0.6378	NPC326316
Remote Similarity	0.6378	NPC474857
Remote Similarity	0.6378	NPC241704
Remote Similarity	0.6378	NPC277669
Remote Similarity	0.6372	NPC213529
Remote Similarity	0.6372	NPC3921
Remote Similarity	0.6369	NPC474915
Remote Similarity	0.6369	NPC213206
Remote Similarity	0.6369	NPC470925
Remote Similarity	0.6369	NPC328750
Remote Similarity	0.6369	NPC188163
Remote Similarity	0.6364	NPC187616
Remote Similarity	0.6364	NPC11147
Remote Similarity	0.6364	NPC473107
Remote Similarity	0.6364	NPC193026
Remote Similarity	0.6364	NPC49603
Remote Similarity	0.6359	NPC219162
Remote Similarity	0.6358	NPC160193
Remote Similarity	0.6355	NPC471812
Remote Similarity	0.6355	NPC471804
Remote Similarity	0.6354	NPC42549
Remote Similarity	0.6354	NPC81247
Remote Similarity	0.6354	NPC195392
Remote Similarity	0.6354	NPC151030
Remote Similarity	0.6354	NPC250846
Remote Similarity	0.6354	NPC317272
Remote Similarity	0.6354	NPC476573
Remote Similarity	0.6354	NPC256012
Remote Similarity	0.6354	NPC476002
Remote Similarity	0.6354	NPC268503
Remote Similarity	0.6354	NPC269383
Remote Similarity	0.6354	NPC240841
Remote Similarity	0.6354	NPC35627
Remote Similarity	0.635	NPC151292
Remote Similarity	0.6349	NPC477080
Remote Similarity	0.6347	NPC263835
Remote Similarity	0.6345	NPC320223
Remote Similarity	0.6345	NPC114364
Remote Similarity	0.6343	NPC325568
Remote Similarity	0.6341	NPC220369
Remote Similarity	0.6341	NPC244403
Remote Similarity	0.6339	NPC51957
Remote Similarity	0.6339	NPC16107
Remote Similarity	0.6339	NPC210437

Drug Structure

NPD3303 OpenBabel08211703112D 26 29 0 0 1 0 0 0 0 0999 V2000 3.8510 -2.9097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6196 -0.2618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5461 -0.4769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9144 -1.2174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9463 0.3232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6887 1.1035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1931 -2.2696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9567 0.1035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3538 -2.1184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6887 0.1035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9705 -1.2946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8227 -0.3965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6737 -1.3853 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8227 1.6035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4600 -2.9497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9567 1.1035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7181 -1.6801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4956 -2.6550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0150 -0.9999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8227 2.6035 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -0.6825 -3.9247 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1.2286 -3.3352 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 3.3510 -2.0436 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0907 1.6035 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0907 2.6035 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 4 1 0 0 0 0 2 10 1 0 0 0 0 3 5 1 0 0 0 0 3 11 1 0 0 0 0 4 23 1 0 0 0 0 5 25 1 0 0 0 0 6 10 2 0 0 0 0 6 14 1 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 12 2 0 0 0 0 8 16 1 0 0 0 0 9 13 1 0 0 0 0 9 23 1 0 0 0 0 10 12 1 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 13 17 1 6 0 0 0 14 16 2 0 0 0 0 14 20 1 0 0 0 0 15 18 2 0 0 0 0 15 21 1 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 19 2 0 0 0 0 18 22 1 0 0 0 0 19 25 1 0 0 0 0 24 26 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB005772
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	397.04
ALogP	2.2457
MLogP	2.89
XLogP	3.4
HDA	1
HBD	1
Rotatable Bonds	6
TPSA	32.7
RO5 Violation	0