NPASS drugs

Drug Information

Drug ID:	NPD2592
Drug Name:	pirsidomine
Molecular Formula:	C17H22N4O3
Canonical SMILES:	COc1ccc(cc1)C(=O)N=c1onn(c1)N1[C@H](C)CCC[C@@H]1C
Standard InCHI:	InChI=1S/C17H22N4O3/c1-12-5-4-6-13(2)21(12)20-11-16(24-19-20)18-17(22)14-7-9-15(23-3)10-8-14/h7-13H,4-6H2,1-3H3/t12-,13+
Standard InCHIKey:	TXPUBJSOHAMNEI-BETUJISGSA-N
Max Developmental Stage:	Discontinued
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD2592

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	200
0.1-0.2	1607
0.2-0.3	6039
0.3-0.4	6152
0.4-0.5	5995
0.5-0.6	10054
0.6-0.7	828
0.7-0.8	15
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	0.7867	NPC266425
Intermediate Similarity	0.7371	NPC28368
Intermediate Similarity	0.7325	NPC471316
Intermediate Similarity	0.729	NPC169766
Intermediate Similarity	0.729	NPC132308
Intermediate Similarity	0.7284	NPC290404
Intermediate Similarity	0.7273	NPC119669
Intermediate Similarity	0.7197	NPC196708
Intermediate Similarity	0.7091	NPC214239
Intermediate Similarity	0.7083	NPC470708
Intermediate Similarity	0.7048	NPC470088
Intermediate Similarity	0.7013	NPC305717
Intermediate Similarity	0.7013	NPC218323
Intermediate Similarity	0.7012	NPC9373
Intermediate Similarity	0.7012	NPC469978
Remote Similarity	0.6988	NPC153644
Remote Similarity	0.6977	NPC135006
Remote Similarity	0.6951	NPC80928
Remote Similarity	0.6923	NPC58661
Remote Similarity	0.6913	NPC469954
Remote Similarity	0.6899	NPC470392
Remote Similarity	0.6897	NPC183648
Remote Similarity	0.6857	NPC66490
Remote Similarity	0.6852	NPC160747
Remote Similarity	0.6849	NPC23332
Remote Similarity	0.6849	NPC57879
Remote Similarity	0.6845	NPC469540
Remote Similarity	0.6845	NPC469539
Remote Similarity	0.6842	NPC319320
Remote Similarity	0.6842	NPC287757
Remote Similarity	0.6839	NPC153631
Remote Similarity	0.6826	NPC324081
Remote Similarity	0.6807	NPC189908
Remote Similarity	0.6805	NPC478189
Remote Similarity	0.6796	NPC270301
Remote Similarity	0.679	NPC225745
Remote Similarity	0.679	NPC470707
Remote Similarity	0.6786	NPC470019
Remote Similarity	0.6784	NPC471649
Remote Similarity	0.6782	NPC26353
Remote Similarity	0.6776	NPC235194
Remote Similarity	0.677	NPC251454
Remote Similarity	0.677	NPC136330
Remote Similarity	0.677	NPC230698
Remote Similarity	0.677	NPC196609
Remote Similarity	0.677	NPC255817
Remote Similarity	0.677	NPC205178
Remote Similarity	0.677	NPC180647
Remote Similarity	0.677	NPC73883
Remote Similarity	0.677	NPC277042
Remote Similarity	0.6761	NPC35345
Remote Similarity	0.6753	NPC158551
Remote Similarity	0.6743	NPC299582
Remote Similarity	0.674	NPC222524
Remote Similarity	0.6728	NPC99078
Remote Similarity	0.6728	NPC307682
Remote Similarity	0.6727	NPC908
Remote Similarity	0.6727	NPC138438
Remote Similarity	0.672	NPC174629
Remote Similarity	0.6711	NPC252004
Remote Similarity	0.6708	NPC29650
Remote Similarity	0.6708	NPC167096
Remote Similarity	0.6688	NPC26285
Remote Similarity	0.6687	NPC252107
Remote Similarity	0.6687	NPC220923
Remote Similarity	0.6686	NPC161544
Remote Similarity	0.6667	NPC256689
Remote Similarity	0.6667	NPC138365
Remote Similarity	0.6667	NPC26589
Remote Similarity	0.6667	NPC67978
Remote Similarity	0.6667	NPC120251
Remote Similarity	0.6667	NPC220540
Remote Similarity	0.6667	NPC160179
Remote Similarity	0.6667	NPC303581
Remote Similarity	0.6667	NPC473444
Remote Similarity	0.6667	NPC471651
Remote Similarity	0.6667	NPC123011
Remote Similarity	0.6649	NPC204970
Remote Similarity	0.6648	NPC86469
Remote Similarity	0.6648	NPC73280
Remote Similarity	0.6646	NPC231572
Remote Similarity	0.6629	NPC206941
Remote Similarity	0.6626	NPC106606
Remote Similarity	0.6624	NPC124776
Remote Similarity	0.6615	NPC163829
Remote Similarity	0.6612	NPC327005
Remote Similarity	0.661	NPC476569
Remote Similarity	0.6609	NPC476443
Remote Similarity	0.6609	NPC133817
Remote Similarity	0.6605	NPC473360
Remote Similarity	0.6604	NPC283079
Remote Similarity	0.6596	NPC28510
Remote Similarity	0.6595	NPC315542
Remote Similarity	0.6593	NPC207721
Remote Similarity	0.6593	NPC308267
Remote Similarity	0.6585	NPC208170
Remote Similarity	0.6585	NPC216149
Remote Similarity	0.6585	NPC238412
Remote Similarity	0.6581	NPC268348
Remote Similarity	0.6578	NPC477259
Remote Similarity	0.6578	NPC169387
Remote Similarity	0.6576	NPC27887
Remote Similarity	0.6559	NPC116007
Remote Similarity	0.6558	NPC17388
Remote Similarity	0.6558	NPC471308
Remote Similarity	0.6558	NPC53596
Remote Similarity	0.6558	NPC289330
Remote Similarity	0.6558	NPC263835
Remote Similarity	0.6558	NPC160120
Remote Similarity	0.6557	NPC35680
Remote Similarity	0.6554	NPC254700
Remote Similarity	0.6548	NPC16188
Remote Similarity	0.6541	NPC172403
Remote Similarity	0.6538	NPC471315
Remote Similarity	0.6538	NPC471314
Remote Similarity	0.6538	NPC329992
Remote Similarity	0.6536	NPC196091
Remote Similarity	0.6524	NPC313694
Remote Similarity	0.6524	NPC242159
Remote Similarity	0.6522	NPC257390
Remote Similarity	0.6522	NPC121400
Remote Similarity	0.6519	NPC164608
Remote Similarity	0.6517	NPC473502
Remote Similarity	0.6513	NPC470860
Remote Similarity	0.651	NPC166837
Remote Similarity	0.6509	NPC130926
Remote Similarity	0.6509	NPC17760
Remote Similarity	0.6509	NPC471646
Remote Similarity	0.6509	NPC471647
Remote Similarity	0.6508	NPC477526
Remote Similarity	0.6506	NPC314682
Remote Similarity	0.6497	NPC472923
Remote Similarity	0.6497	NPC217277
Remote Similarity	0.6494	NPC43275
Remote Similarity	0.6494	NPC56635
Remote Similarity	0.6494	NPC61779
Remote Similarity	0.6492	NPC198401
Remote Similarity	0.6488	NPC473804
Remote Similarity	0.6486	NPC99723
Remote Similarity	0.6485	NPC28641
Remote Similarity	0.6485	NPC194359
Remote Similarity	0.6481	NPC328070
Remote Similarity	0.648	NPC231198
Remote Similarity	0.6477	NPC71124
Remote Similarity	0.6474	NPC476579
Remote Similarity	0.6474	NPC476568
Remote Similarity	0.6471	NPC323948
Remote Similarity	0.6467	NPC213206
Remote Similarity	0.6467	NPC328750
Remote Similarity	0.6467	NPC188163
Remote Similarity	0.6467	NPC474915
Remote Similarity	0.646	NPC160193
Remote Similarity	0.6457	NPC169742
Remote Similarity	0.6456	NPC221798
Remote Similarity	0.6455	NPC283207
Remote Similarity	0.6455	NPC208890
Remote Similarity	0.645	NPC119569
Remote Similarity	0.6448	NPC143450
Remote Similarity	0.6447	NPC303370
Remote Similarity	0.6441	NPC118804
Remote Similarity	0.6433	NPC223873
Remote Similarity	0.6429	NPC293424
Remote Similarity	0.6422	NPC313327
Remote Similarity	0.642	NPC308885
Remote Similarity	0.642	NPC255550
Remote Similarity	0.642	NPC45191
Remote Similarity	0.642	NPC57512
Remote Similarity	0.6419	NPC309982
Remote Similarity	0.6417	NPC473007
Remote Similarity	0.6415	NPC476249
Remote Similarity	0.6415	NPC470858
Remote Similarity	0.6415	NPC473626
Remote Similarity	0.641	NPC295317
Remote Similarity	0.641	NPC225245
Remote Similarity	0.6407	NPC33011
Remote Similarity	0.6407	NPC83289
Remote Similarity	0.6407	NPC189724
Remote Similarity	0.6407	NPC212850
Remote Similarity	0.6405	NPC19290
Remote Similarity	0.6402	NPC94280
Remote Similarity	0.6402	NPC45783
Remote Similarity	0.6402	NPC103947
Remote Similarity	0.6402	NPC159150
Remote Similarity	0.6402	NPC328419
Remote Similarity	0.6402	NPC471650
Remote Similarity	0.6402	NPC193673
Remote Similarity	0.64	NPC54626
Remote Similarity	0.6398	NPC2596
Remote Similarity	0.6398	NPC314659
Remote Similarity	0.6392	NPC11799
Remote Similarity	0.6392	NPC474691
Remote Similarity	0.6392	NPC211218
Remote Similarity	0.6392	NPC141252
Remote Similarity	0.6389	NPC186617
Remote Similarity	0.6386	NPC253429
Remote Similarity	0.6386	NPC471201
Remote Similarity	0.6384	NPC93653
Remote Similarity	0.6383	NPC83511
Remote Similarity	0.6383	NPC87391
Remote Similarity	0.638	NPC93882

Drug Structure

NPD2592 OpenBabel08211702172D 24 26 0 0 1 0 0 0 0 0999 V2000 3.3147 -0.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2469 1.2474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4836 -1.1796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0823 -0.1615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0714 -0.3706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6701 0.6475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 0.3364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4487 1.8364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4890 -1.0751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6646 0.5430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9013 -1.8841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0933 -1.7796 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 0.3364 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 0.8364 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3080 -2.7976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2524 1.3520 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 3 23 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 9 1 0 0 0 0 7 14 2 0 0 0 0 8 10 2 0 0 0 0 8 14 1 0 0 0 0 9 15 2 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 11 20 2 0 0 0 0 12 1 1 6 0 0 0 12 21 1 0 0 0 0 13 2 1 6 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 15 23 1 0 0 0 0 16 18 2 3 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 22 2 0 0 0 0 19 20 2 0 0 0 0 19 24 1 0 0 0 0 20 21 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB005215
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	330.17
ALogP	-1.3157
MLogP	2.56
XLogP	2.54
HDA	4
HBD	0
Rotatable Bonds	7
TPSA	75.17
RO5 Violation	0