NPASS drugs

Drug Information

Drug ID:	NPD1499
Drug Name:	Lonidamine
Molecular Formula:	C15H10Cl2N2O2
Canonical SMILES:	Clc1ccc(c(c1)Cl)Cn1nc(c2c1cccc2)C(=O)O
Standard InCHI:	InChI=1S/C15H10Cl2N2O2/c16-10-6-5-9(12(17)7-10)8-19-13-4-2-1-3-11(13)14(18-19)15(20)21/h1-7H,8H2,(H,20,21)
Standard InCHIKey:	WDRYRZXSPDWGEB-UHFFFAOYSA-N
Max Developmental Stage:	Phase 3
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD1499

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	310
0.1-0.2	2635
0.2-0.3	9995
0.3-0.4	12393
0.4-0.5	3184
0.5-0.6	2117
0.6-0.7	253
0.7-0.8	3
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	0.7273	NPC322644
Intermediate Similarity	0.7166	NPC477887
Intermediate Similarity	0.7033	NPC477890
Remote Similarity	0.6986	NPC57398
Remote Similarity	0.6931	NPC278434
Remote Similarity	0.6875	NPC474916
Remote Similarity	0.6869	NPC219848
Remote Similarity	0.6857	NPC471944
Remote Similarity	0.6856	NPC41717
Remote Similarity	0.6835	NPC62995
Remote Similarity	0.6834	NPC256268
Remote Similarity	0.683	NPC192712
Remote Similarity	0.6827	NPC141454
Remote Similarity	0.6816	NPC243058
Remote Similarity	0.6806	NPC82370
Remote Similarity	0.6768	NPC303225
Remote Similarity	0.6749	NPC282103
Remote Similarity	0.674	NPC315062
Remote Similarity	0.6739	NPC104712
Remote Similarity	0.6716	NPC90415
Remote Similarity	0.6711	NPC244897
Remote Similarity	0.67	NPC207851
Remote Similarity	0.67	NPC203635
Remote Similarity	0.6699	NPC471593
Remote Similarity	0.6699	NPC83111
Remote Similarity	0.6667	NPC267853
Remote Similarity	0.6652	NPC316411
Remote Similarity	0.665	NPC221873
Remote Similarity	0.6636	NPC165599
Remote Similarity	0.662	NPC244741
Remote Similarity	0.6619	NPC472193
Remote Similarity	0.6596	NPC259678
Remote Similarity	0.6589	NPC328596
Remote Similarity	0.6589	NPC328318
Remote Similarity	0.6587	NPC138370
Remote Similarity	0.6553	NPC194040
Remote Similarity	0.6549	NPC229893
Remote Similarity	0.6538	NPC144381
Remote Similarity	0.6535	NPC111275
Remote Similarity	0.6524	NPC230403
Remote Similarity	0.6517	NPC469938
Remote Similarity	0.6516	NPC317752
Remote Similarity	0.6514	NPC266249
Remote Similarity	0.6498	NPC317373
Remote Similarity	0.6493	NPC276517
Remote Similarity	0.6485	NPC84347
Remote Similarity	0.6479	NPC131887
Remote Similarity	0.6473	NPC160381
Remote Similarity	0.6471	NPC318299
Remote Similarity	0.6455	NPC123839
Remote Similarity	0.6455	NPC309845
Remote Similarity	0.6452	NPC327592
Remote Similarity	0.645	NPC119006
Remote Similarity	0.6441	NPC89508
Remote Similarity	0.644	NPC300596
Remote Similarity	0.644	NPC237649
Remote Similarity	0.6436	NPC149155
Remote Similarity	0.6436	NPC110500
Remote Similarity	0.6436	NPC203468
Remote Similarity	0.6432	NPC90229
Remote Similarity	0.6425	NPC241025
Remote Similarity	0.6419	NPC315491
Remote Similarity	0.6419	NPC45459
Remote Similarity	0.6417	NPC85443
Remote Similarity	0.6413	NPC237740
Remote Similarity	0.641	NPC141353
Remote Similarity	0.641	NPC477889
Remote Similarity	0.6408	NPC159125
Remote Similarity	0.6404	NPC267885
Remote Similarity	0.6402	NPC102008
Remote Similarity	0.6402	NPC67288
Remote Similarity	0.6396	NPC118940
Remote Similarity	0.6393	NPC270918
Remote Similarity	0.6393	NPC321428
Remote Similarity	0.6384	NPC36405
Remote Similarity	0.6373	NPC15573
Remote Similarity	0.6373	NPC217372
Remote Similarity	0.6373	NPC157583
Remote Similarity	0.6373	NPC183662
Remote Similarity	0.6364	NPC476231
Remote Similarity	0.6356	NPC472285
Remote Similarity	0.6356	NPC312645
Remote Similarity	0.6343	NPC213308
Remote Similarity	0.6341	NPC248041
Remote Similarity	0.6341	NPC126709
Remote Similarity	0.6341	NPC283219
Remote Similarity	0.6341	NPC219336
Remote Similarity	0.634	NPC35042
Remote Similarity	0.6338	NPC202812
Remote Similarity	0.6336	NPC472844
Remote Similarity	0.6333	NPC321708
Remote Similarity	0.633	NPC476098
Remote Similarity	0.6326	NPC306376
Remote Similarity	0.6326	NPC472284
Remote Similarity	0.6318	NPC193238
Remote Similarity	0.6318	NPC78020
Remote Similarity	0.6316	NPC62749
Remote Similarity	0.6313	NPC131718
Remote Similarity	0.6313	NPC27904
Remote Similarity	0.6311	NPC475685
Remote Similarity	0.6303	NPC154339
Remote Similarity	0.6302	NPC302159
Remote Similarity	0.6301	NPC132539
Remote Similarity	0.6283	NPC27041
Remote Similarity	0.6279	NPC134657
Remote Similarity	0.6267	NPC477979
Remote Similarity	0.6262	NPC213468
Remote Similarity	0.6262	NPC55772
Remote Similarity	0.6256	NPC158129
Remote Similarity	0.6256	NPC273532
Remote Similarity	0.6255	NPC323198
Remote Similarity	0.6245	NPC15801
Remote Similarity	0.6244	NPC243850
Remote Similarity	0.6243	NPC43477
Remote Similarity	0.6233	NPC472116
Remote Similarity	0.6229	NPC182222
Remote Similarity	0.6227	NPC472259
Remote Similarity	0.6227	NPC314648
Remote Similarity	0.6223	NPC181527
Remote Similarity	0.6221	NPC280714
Remote Similarity	0.6216	NPC39679
Remote Similarity	0.6215	NPC267343
Remote Similarity	0.6214	NPC293472
Remote Similarity	0.6201	NPC276657
Remote Similarity	0.62	NPC88970
Remote Similarity	0.6199	NPC82053
Remote Similarity	0.6195	NPC118228
Remote Similarity	0.619	NPC295158
Remote Similarity	0.6188	NPC325297
Remote Similarity	0.6179	NPC183805
Remote Similarity	0.6176	NPC302647
Remote Similarity	0.6173	NPC161801
Remote Similarity	0.6171	NPC283117
Remote Similarity	0.6169	NPC102423
Remote Similarity	0.6169	NPC189116
Remote Similarity	0.6168	NPC472292
Remote Similarity	0.6167	NPC322064
Remote Similarity	0.6161	NPC315555
Remote Similarity	0.6161	NPC235684
Remote Similarity	0.6157	NPC74360
Remote Similarity	0.615	NPC250448
Remote Similarity	0.6147	NPC81535
Remote Similarity	0.6147	NPC478141
Remote Similarity	0.6147	NPC241024
Remote Similarity	0.6146	NPC252572
Remote Similarity	0.6143	NPC171787
Remote Similarity	0.6143	NPC470003
Remote Similarity	0.614	NPC81802
Remote Similarity	0.614	NPC472210
Remote Similarity	0.614	NPC247735
Remote Similarity	0.614	NPC269886
Remote Similarity	0.614	NPC472295
Remote Similarity	0.6139	NPC471130
Remote Similarity	0.6135	NPC14113
Remote Similarity	0.6135	NPC237188
Remote Similarity	0.6135	NPC84827
Remote Similarity	0.6135	NPC145885
Remote Similarity	0.6133	NPC294375
Remote Similarity	0.6133	NPC87413
Remote Similarity	0.6132	NPC473815
Remote Similarity	0.6129	NPC227582
Remote Similarity	0.6129	NPC156704
Remote Similarity	0.6127	NPC477888
Remote Similarity	0.6126	NPC314855
Remote Similarity	0.6126	NPC313796
Remote Similarity	0.6126	NPC313345
Remote Similarity	0.6126	NPC472287
Remote Similarity	0.6126	NPC472286
Remote Similarity	0.6126	NPC175602
Remote Similarity	0.6126	NPC315638
Remote Similarity	0.6124	NPC192270
Remote Similarity	0.6124	NPC71037
Remote Similarity	0.6124	NPC113626
Remote Similarity	0.6119	NPC242116
Remote Similarity	0.6117	NPC475594
Remote Similarity	0.6114	NPC184408
Remote Similarity	0.6114	NPC264285
Remote Similarity	0.6109	NPC240384
Remote Similarity	0.6106	NPC219087
Remote Similarity	0.6106	NPC474041
Remote Similarity	0.6103	NPC255909
Remote Similarity	0.6102	NPC300114
Remote Similarity	0.6101	NPC212213
Remote Similarity	0.6099	NPC53344
Remote Similarity	0.6099	NPC315545
Remote Similarity	0.6099	NPC314297
Remote Similarity	0.6098	NPC6982
Remote Similarity	0.6096	NPC253476
Remote Similarity	0.6096	NPC469928
Remote Similarity	0.6095	NPC143533
Remote Similarity	0.6095	NPC48938
Remote Similarity	0.6091	NPC98864
Remote Similarity	0.6087	NPC288785
Remote Similarity	0.6087	NPC475607
Remote Similarity	0.6087	NPC134586
Remote Similarity	0.6083	NPC472293
Remote Similarity	0.6082	NPC478039
Remote Similarity	0.6079	NPC31700
Remote Similarity	0.6078	NPC216612
Remote Similarity	0.6078	NPC470894

Drug Structure

NPD1499 OpenBabel08211701082D 22 24 0 0 0 0 0 0 0 0999 V2000 2.8698 -0.8226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2007 -1.5657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5608 0.1285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2226 -1.3578 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 -0.0000 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 -0.8660 -0.5000 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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 0.3364 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 0.9135 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4894 2.1160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 0.9945 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 2.4839 2.2205 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9016 2.9250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8907 3.1341 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 11 2 0 0 0 0 4 13 2 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 10 2 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 12 2 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 14 1 0 0 0 0 12 17 1 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 18 2 0 0 0 0 15 20 1 0 0 0 0 15 21 2 0 0 0 0 18 19 1 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DCL000153
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	39562
ChEBI
CAS Number

Drug Properties

Molecular Weight	320.01
ALogP	1.2736
MLogP	2.45
XLogP	3.917
HDA	4
HBD	1
Rotatable Bonds	6
TPSA	55.12
RO5 Violation	0