NPASS drugs

Drug Information

Drug ID:	NPD5189
Drug Name:
Molecular Formula:	C22H28N2O3S
Canonical SMILES:	CCC(C(=O)O)(CC(=Nc1cccc(c1)/C=C/c1scc(n1)C(C)C)O)CC
Standard InCHI:	InChI=1S/C22H28N2O3S/c1-5-22(6-2,21(26)27)13-19(25)23-17-9-7-8-16(12-17)10-11-20-24-18(14-28-20)15(3)4/h7-12,14-15H,5-6,13H2,1-4H3,(H,23,25)(H,26,27)/b11-10+
Standard InCHIKey:	PGLNVMJTDKEOBE-ZHACJKMWSA-N
Max Developmental Stage:	Clinical (unspecified phase)
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD5189

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	150
0.1-0.2	1538
0.2-0.3	10115
0.3-0.4	14464
0.4-0.5	2905
0.5-0.6	1571
0.6-0.7	143
0.7-0.8	4
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	0.7127	NPC329961
Intermediate Similarity	0.7127	NPC122427
Intermediate Similarity	0.7049	NPC165538
Intermediate Similarity	0.7	NPC49051
Remote Similarity	0.6966	NPC249662
Remote Similarity	0.6954	NPC476103
Remote Similarity	0.6906	NPC96016
Remote Similarity	0.6897	NPC24990
Remote Similarity	0.6883	NPC273714
Remote Similarity	0.6854	NPC161242
Remote Similarity	0.6839	NPC151779
Remote Similarity	0.6805	NPC161108
Remote Similarity	0.6778	NPC263485
Remote Similarity	0.6778	NPC25316
Remote Similarity	0.6778	NPC229160
Remote Similarity	0.6768	NPC88121
Remote Similarity	0.676	NPC475534
Remote Similarity	0.676	NPC476080
Remote Similarity	0.6739	NPC238242
Remote Similarity	0.6722	NPC475330
Remote Similarity	0.6703	NPC188104
Remote Similarity	0.6685	NPC174652
Remote Similarity	0.6646	NPC474070
Remote Similarity	0.6645	NPC475568
Remote Similarity	0.6624	NPC475604
Remote Similarity	0.6554	NPC475920
Remote Similarity	0.6545	NPC272483
Remote Similarity	0.6522	NPC161143
Remote Similarity	0.6515	NPC145178
Remote Similarity	0.6515	NPC475350
Remote Similarity	0.6515	NPC14877
Remote Similarity	0.6494	NPC474538
Remote Similarity	0.6488	NPC319751
Remote Similarity	0.6456	NPC69277
Remote Similarity	0.6453	NPC163147
Remote Similarity	0.6453	NPC252616
Remote Similarity	0.6453	NPC109498
Remote Similarity	0.6453	NPC32583
Remote Similarity	0.6453	NPC474090
Remote Similarity	0.6453	NPC45576
Remote Similarity	0.6453	NPC61667
Remote Similarity	0.6438	NPC287895
Remote Similarity	0.6418	NPC251036
Remote Similarity	0.6416	NPC224609
Remote Similarity	0.6416	NPC268063
Remote Similarity	0.6395	NPC474067
Remote Similarity	0.6395	NPC148592
Remote Similarity	0.6395	NPC475737
Remote Similarity	0.6395	NPC474094
Remote Similarity	0.6395	NPC185665
Remote Similarity	0.6391	NPC474069
Remote Similarity	0.6379	NPC202591
Remote Similarity	0.6379	NPC212214
Remote Similarity	0.6374	NPC469938
Remote Similarity	0.6374	NPC119481
Remote Similarity	0.6359	NPC213468
Remote Similarity	0.6358	NPC154873
Remote Similarity	0.6343	NPC21126
Remote Similarity	0.6337	NPC475683
Remote Similarity	0.6337	NPC157194
Remote Similarity	0.6337	NPC474080
Remote Similarity	0.6337	NPC21449
Remote Similarity	0.6337	NPC474079
Remote Similarity	0.6337	NPC474102
Remote Similarity	0.6331	NPC190329
Remote Similarity	0.6316	NPC473398
Remote Similarity	0.6312	NPC476140
Remote Similarity	0.6307	NPC52587
Remote Similarity	0.6307	NPC127775
Remote Similarity	0.6304	NPC248454
Remote Similarity	0.6294	NPC242556
Remote Similarity	0.6279	NPC474103
Remote Similarity	0.6279	NPC82436
Remote Similarity	0.6279	NPC474068
Remote Similarity	0.6279	NPC474064
Remote Similarity	0.6271	NPC231110
Remote Similarity	0.6269	NPC239660
Remote Similarity	0.6269	NPC106235
Remote Similarity	0.6264	NPC216713
Remote Similarity	0.6264	NPC206724
Remote Similarity	0.6264	NPC474515
Remote Similarity	0.625	NPC285469
Remote Similarity	0.6243	NPC37548
Remote Similarity	0.6237	NPC164228
Remote Similarity	0.6236	NPC312887
Remote Similarity	0.6229	NPC200743
Remote Similarity	0.6175	NPC6982
Remote Similarity	0.6175	NPC126492
Remote Similarity	0.6173	NPC278451
Remote Similarity	0.617	NPC163055
Remote Similarity	0.6158	NPC184476
Remote Similarity	0.6149	NPC124005
Remote Similarity	0.6149	NPC187951
Remote Similarity	0.6135	NPC79386
Remote Similarity	0.6129	NPC64436
Remote Similarity	0.6126	NPC472323
Remote Similarity	0.6124	NPC299594
Remote Similarity	0.6124	NPC129721
Remote Similarity	0.6124	NPC315252
Remote Similarity	0.612	NPC280548
Remote Similarity	0.6111	NPC16667
Remote Similarity	0.6103	NPC85066
Remote Similarity	0.6103	NPC181502
Remote Similarity	0.6102	NPC207726
Remote Similarity	0.6102	NPC38736
Remote Similarity	0.6102	NPC471458
Remote Similarity	0.6102	NPC470507
Remote Similarity	0.61	NPC75498
Remote Similarity	0.6096	NPC248462
Remote Similarity	0.6092	NPC471957
Remote Similarity	0.6075	NPC267885
Remote Similarity	0.6066	NPC78020
Remote Similarity	0.6066	NPC470146
Remote Similarity	0.6066	NPC101980
Remote Similarity	0.6066	NPC97078
Remote Similarity	0.6059	NPC104483
Remote Similarity	0.6059	NPC468984
Remote Similarity	0.6045	NPC469760
Remote Similarity	0.6045	NPC25008
Remote Similarity	0.6045	NPC469763
Remote Similarity	0.6045	NPC73952
Remote Similarity	0.6045	NPC259644
Remote Similarity	0.6045	NPC469786
Remote Similarity	0.6045	NPC469765
Remote Similarity	0.6034	NPC129042
Remote Similarity	0.6025	NPC317758
Remote Similarity	0.6023	NPC238499
Remote Similarity	0.6022	NPC203468
Remote Similarity	0.6022	NPC110500
Remote Similarity	0.6022	NPC149155
Remote Similarity	0.602	NPC143325
Remote Similarity	0.602	NPC294693
Remote Similarity	0.602	NPC138562
Remote Similarity	0.6011	NPC211572
Remote Similarity	0.6011	NPC80597
Remote Similarity	0.6011	NPC75540
Remote Similarity	0.6011	NPC70922
Remote Similarity	0.6011	NPC248041
Remote Similarity	0.6011	NPC219336
Remote Similarity	0.6011	NPC470509
Remote Similarity	0.6011	NPC126709
Remote Similarity	0.6011	NPC212376
Remote Similarity	0.601	NPC175474
Remote Similarity	0.6	NPC67056
Remote Similarity	0.6	NPC243058
Remote Similarity	0.6	NPC159125
Remote Similarity	0.6	NPC474791
Remote Similarity	0.5991	NPC475196
Remote Similarity	0.599	NPC235684
Remote Similarity	0.5989	NPC472587
Remote Similarity	0.5989	NPC470823
Remote Similarity	0.5989	NPC271734
Remote Similarity	0.5989	NPC8104
Remote Similarity	0.5988	NPC277157
Remote Similarity	0.5979	NPC15840
Remote Similarity	0.5979	NPC206967
Remote Similarity	0.5977	NPC285731
Remote Similarity	0.5977	NPC314372
Remote Similarity	0.5969	NPC470003
Remote Similarity	0.5969	NPC472119
Remote Similarity	0.5969	NPC203635
Remote Similarity	0.5968	NPC477976
Remote Similarity	0.5967	NPC473320
Remote Similarity	0.5963	NPC41174
Remote Similarity	0.5957	NPC15573
Remote Similarity	0.5957	NPC28848
Remote Similarity	0.5957	NPC217372
Remote Similarity	0.5957	NPC14325
Remote Similarity	0.5957	NPC183662
Remote Similarity	0.5955	NPC200214
Remote Similarity	0.5952	NPC149014
Remote Similarity	0.5949	NPC81561
Remote Similarity	0.5947	NPC113626
Remote Similarity	0.5946	NPC474168
Remote Similarity	0.5944	NPC469762
Remote Similarity	0.5939	NPC289299
Remote Similarity	0.5939	NPC57994
Remote Similarity	0.5938	NPC280290
Remote Similarity	0.5934	NPC194881
Remote Similarity	0.593	NPC52557
Remote Similarity	0.5926	NPC283219
Remote Similarity	0.5924	NPC160105
Remote Similarity	0.5924	NPC474561
Remote Similarity	0.5924	NPC49954
Remote Similarity	0.5916	NPC143533
Remote Similarity	0.5914	NPC158129
Remote Similarity	0.5909	NPC477134
Remote Similarity	0.5907	NPC90415
Remote Similarity	0.5907	NPC99428
Remote Similarity	0.5905	NPC173344
Remote Similarity	0.5902	NPC476118
Remote Similarity	0.5902	NPC311276
Remote Similarity	0.5899	NPC14101
Remote Similarity	0.5897	NPC329858
Remote Similarity	0.5897	NPC314333
Remote Similarity	0.5895	NPC222592
Remote Similarity	0.5895	NPC91179
Remote Similarity	0.5895	NPC168486
Remote Similarity	0.5892	NPC154293
Remote Similarity	0.5892	NPC201700

Drug Structure

NPD5189 OpenBabel08211706322D 30 31 0 0 0 0 0 0 0 0999 V2000 -6.9757 4.8253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8417 4.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0119 -3.3317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5704 -2.6272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4757 3.9593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8417 3.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5759 -2.5227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 3.0933 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 -7.4757 2.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9757 3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 2.5933 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.4013 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 4.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4757 2.2272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9757 1.3612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 4.5933 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4757 0.4952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 6 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 22 1 0 0 0 0 6 22 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 10 11 2 0 0 0 0 10 16 1 0 0 0 0 11 20 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 13 19 1 0 0 0 0 13 22 1 0 0 0 0 14 18 2 0 0 0 0 14 28 1 0 0 0 0 15 18 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 23 2 3 0 0 0 19 25 1 0 0 0 0 20 24 2 0 0 0 0 20 28 1 0 0 0 0 21 22 1 0 0 0 0 21 26 2 0 0 0 0 21 27 1 0 0 0 0 25 29 1 0 0 0 0 27 30 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB008196
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	6439428
ChEBI
CAS Number

Drug Properties

Molecular Weight	400.18
ALogP	1.5887
MLogP	3.22
XLogP	6.205
HDA	5
HBD	2
Rotatable Bonds	15
TPSA	111.02
RO5 Violation	1