NPASS drugs

Drug Information

Drug ID:	NPD6857
Drug Name:	Retosiban
Molecular Formula:	C27H34N4O5
Canonical SMILES:	CC[C@@H]([C@@H]1C(=N[C@@H](C(=O)N1[C@@H](C(=O)N1CCOCC1)c1coc(n1)C)C1Cc2c(C1)cccc2)O)C
Standard InCHI:	InChI=1S/C27H34N4O5/c1-4-16(2)23-25(32)29-22(20-13-18-7-5-6-8-19(18)14-20)26(33)31(23)24(21-15-36-17(3)28-21)27(34)30-9-11-35-12-10-30/h5-8,15-16,20,22-24H,4,9-14H2,1-3H3,(H,29,32)/t16-,22+,23+,24+/m0/s1
Standard InCHIKey:	PLVGDGRBPMVYPB-FDUHJNRSSA-N
Max Developmental Stage:	Phase 3
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD6857

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	223
0.1-0.2	1284
0.2-0.3	8330
0.3-0.4	11114
0.4-0.5	7165
0.5-0.6	2624
0.6-0.7	149
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	0.7005	NPC49195
Remote Similarity	0.6818	NPC315804
Remote Similarity	0.6818	NPC313804
Remote Similarity	0.6753	NPC477585
Remote Similarity	0.6753	NPC477588
Remote Similarity	0.6753	NPC477586
Remote Similarity	0.6753	NPC477590
Remote Similarity	0.6667	NPC477589
Remote Similarity	0.6667	NPC75179
Remote Similarity	0.6667	NPC477587
Remote Similarity	0.6535	NPC186351
Remote Similarity	0.6429	NPC117244
Remote Similarity	0.6429	NPC473763
Remote Similarity	0.6398	NPC165538
Remote Similarity	0.6393	NPC316403
Remote Similarity	0.639	NPC91179
Remote Similarity	0.6316	NPC66210
Remote Similarity	0.6316	NPC478077
Remote Similarity	0.6303	NPC122427
Remote Similarity	0.63	NPC254700
Remote Similarity	0.6298	NPC472119
Remote Similarity	0.6298	NPC228835
Remote Similarity	0.6294	NPC104345
Remote Similarity	0.6293	NPC191382
Remote Similarity	0.6293	NPC56109
Remote Similarity	0.6293	NPC194740
Remote Similarity	0.6288	NPC155444
Remote Similarity	0.6277	NPC263493
Remote Similarity	0.6277	NPC269398
Remote Similarity	0.6263	NPC209509
Remote Similarity	0.6261	NPC475350
Remote Similarity	0.6261	NPC14877
Remote Similarity	0.6261	NPC145178
Remote Similarity	0.6257	NPC178662
Remote Similarity	0.6257	NPC470884
Remote Similarity	0.6257	NPC98424
Remote Similarity	0.6257	NPC476133
Remote Similarity	0.6257	NPC92784
Remote Similarity	0.6256	NPC281049
Remote Similarity	0.6256	NPC303658
Remote Similarity	0.625	NPC251036
Remote Similarity	0.625	NPC314523
Remote Similarity	0.625	NPC58001
Remote Similarity	0.6245	NPC184680
Remote Similarity	0.6243	NPC161069
Remote Similarity	0.6238	NPC471651
Remote Similarity	0.6238	NPC30527
Remote Similarity	0.623	NPC262077
Remote Similarity	0.6226	NPC329961
Remote Similarity	0.6221	NPC293917
Remote Similarity	0.6218	NPC470785
Remote Similarity	0.6218	NPC474183
Remote Similarity	0.6214	NPC14325
Remote Similarity	0.6214	NPC28848
Remote Similarity	0.6213	NPC102593
Remote Similarity	0.6213	NPC196718
Remote Similarity	0.6209	NPC472323
Remote Similarity	0.6193	NPC476829
Remote Similarity	0.6183	NPC316224
Remote Similarity	0.6178	NPC472098
Remote Similarity	0.6175	NPC473322
Remote Similarity	0.6173	NPC161801
Remote Similarity	0.6172	NPC143533
Remote Similarity	0.6168	NPC472113
Remote Similarity	0.6161	NPC94752
Remote Similarity	0.6154	NPC15840
Remote Similarity	0.6151	NPC470784
Remote Similarity	0.6147	NPC478141
Remote Similarity	0.6146	NPC161861
Remote Similarity	0.6143	NPC470003
Remote Similarity	0.6143	NPC258480
Remote Similarity	0.6132	NPC17059
Remote Similarity	0.6126	NPC277350
Remote Similarity	0.6124	NPC113626
Remote Similarity	0.6121	NPC129909
Remote Similarity	0.6121	NPC64216
Remote Similarity	0.6118	NPC329631
Remote Similarity	0.6118	NPC141053
Remote Similarity	0.6116	NPC478158
Remote Similarity	0.6114	NPC472107
Remote Similarity	0.6114	NPC79062
Remote Similarity	0.6114	NPC138775
Remote Similarity	0.6111	NPC106235
Remote Similarity	0.6111	NPC239660
Remote Similarity	0.6111	NPC289299
Remote Similarity	0.6111	NPC257851
Remote Similarity	0.6111	NPC57994
Remote Similarity	0.6106	NPC264176
Remote Similarity	0.6106	NPC11126
Remote Similarity	0.6098	NPC471648
Remote Similarity	0.6095	NPC470205
Remote Similarity	0.6095	NPC161143
Remote Similarity	0.6095	NPC159125
Remote Similarity	0.6092	NPC196449
Remote Similarity	0.6092	NPC314222
Remote Similarity	0.6089	NPC200964
Remote Similarity	0.6083	NPC472116
Remote Similarity	0.6082	NPC240848
Remote Similarity	0.608	NPC471649
Remote Similarity	0.6078	NPC253987
Remote Similarity	0.6071	NPC287208
Remote Similarity	0.607	NPC305984
Remote Similarity	0.607	NPC211555
Remote Similarity	0.6068	NPC137627
Remote Similarity	0.6068	NPC477976
Remote Similarity	0.6068	NPC24370
Remote Similarity	0.6068	NPC319232
Remote Similarity	0.6061	NPC128115
Remote Similarity	0.6058	NPC234987
Remote Similarity	0.6054	NPC200589
Remote Similarity	0.6053	NPC478157
Remote Similarity	0.6043	NPC124920
Remote Similarity	0.6043	NPC309919
Remote Similarity	0.6043	NPC34580
Remote Similarity	0.6043	NPC304307
Remote Similarity	0.6043	NPC118559
Remote Similarity	0.6042	NPC476978
Remote Similarity	0.6042	NPC52748
Remote Similarity	0.6041	NPC122590
Remote Similarity	0.604	NPC194881
Remote Similarity	0.604	NPC471052
Remote Similarity	0.604	NPC471051
Remote Similarity	0.604	NPC471053
Remote Similarity	0.6039	NPC477462
Remote Similarity	0.6039	NPC279871
Remote Similarity	0.6039	NPC469938
Remote Similarity	0.6038	NPC133003
Remote Similarity	0.6035	NPC38237
Remote Similarity	0.6032	NPC471264
Remote Similarity	0.6032	NPC133609
Remote Similarity	0.6032	NPC471265
Remote Similarity	0.6028	NPC213629
Remote Similarity	0.6027	NPC54420
Remote Similarity	0.6022	NPC255447
Remote Similarity	0.602	NPC186452
Remote Similarity	0.6017	NPC100547
Remote Similarity	0.6016	NPC472436
Remote Similarity	0.601	NPC5620
Remote Similarity	0.601	NPC472923
Remote Similarity	0.6009	NPC151781
Remote Similarity	0.6009	NPC316181
Remote Similarity	0.6009	NPC74562
Remote Similarity	0.6009	NPC54744
Remote Similarity	0.6009	NPC311858
Remote Similarity	0.6008	NPC89987
Remote Similarity	0.6	NPC61011
Remote Similarity	0.6	NPC472112
Remote Similarity	0.6	NPC315467
Remote Similarity	0.6	NPC73994
Remote Similarity	0.6	NPC9373
Remote Similarity	0.5992	NPC223409
Remote Similarity	0.5992	NPC95240
Remote Similarity	0.5992	NPC322135
Remote Similarity	0.5991	NPC46895
Remote Similarity	0.599	NPC139326
Remote Similarity	0.5989	NPC474082
Remote Similarity	0.5989	NPC6975
Remote Similarity	0.5989	NPC175726
Remote Similarity	0.5983	NPC205372
Remote Similarity	0.5983	NPC476826
Remote Similarity	0.5983	NPC323198
Remote Similarity	0.5983	NPC476831
Remote Similarity	0.5983	NPC284888
Remote Similarity	0.5983	NPC323752
Remote Similarity	0.5983	NPC476827
Remote Similarity	0.5982	NPC472541
Remote Similarity	0.5982	NPC472287
Remote Similarity	0.5982	NPC472542
Remote Similarity	0.5982	NPC472286
Remote Similarity	0.5975	NPC325683
Remote Similarity	0.5975	NPC261251
Remote Similarity	0.5975	NPC244536
Remote Similarity	0.5974	NPC131885
Remote Similarity	0.5974	NPC477714
Remote Similarity	0.5973	NPC121327
Remote Similarity	0.5973	NPC162860
Remote Similarity	0.5972	NPC243716
Remote Similarity	0.5972	NPC472097
Remote Similarity	0.5971	NPC40234
Remote Similarity	0.5971	NPC65080
Remote Similarity	0.597	NPC287757
Remote Similarity	0.597	NPC319320
Remote Similarity	0.5969	NPC2501
Remote Similarity	0.5969	NPC239762
Remote Similarity	0.5969	NPC163392
Remote Similarity	0.5966	NPC14288
Remote Similarity	0.5965	NPC75634
Remote Similarity	0.5962	NPC476227
Remote Similarity	0.5962	NPC26108
Remote Similarity	0.5961	NPC472101
Remote Similarity	0.5961	NPC472120
Remote Similarity	0.5961	NPC472117
Remote Similarity	0.596	NPC472435
Remote Similarity	0.5959	NPC472434
Remote Similarity	0.5957	NPC477219
Remote Similarity	0.5957	NPC476830
Remote Similarity	0.5956	NPC53344
Remote Similarity	0.5955	NPC472284
Remote Similarity	0.5955	NPC473640
Remote Similarity	0.5955	NPC315276

Drug Structure

NPD6857 OpenBabel08211710072D 37 41 0 0 1 0 0 0 0 0999 V2000 2.5362 -3.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9073 3.7562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -2.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5455 1.6619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0574 2.5073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0574 0.8165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0812 2.5073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3816 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2270 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3816 1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4280 0.0910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6383 1.4589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0557 2.0381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -1.9524 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3335 2.9665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0812 0.8165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5931 1.6619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8454 0.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8454 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6352 2.0381 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 -0.9762 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 0.4881 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 -0.8454 -2.4405 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 1.4643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -0.9762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2270 1.4643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3573 2.9665 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 -2.9286 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 3 17 1 0 0 0 0 4 16 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 18 2 0 0 0 0 8 19 2 0 0 0 0 9 11 1 0 0 0 0 9 30 1 0 0 0 0 10 12 1 0 0 0 0 10 30 1 0 0 0 0 11 35 1 0 0 0 0 12 35 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 0 0 0 0 15 21 2 0 0 0 0 15 36 1 0 0 0 0 16 2 1 1 0 0 0 17 28 2 0 0 0 0 17 36 1 0 0 0 0 18 19 1 0 0 0 0 21 24 1 0 0 0 0 21 28 1 0 0 0 0 22 20 1 6 0 0 0 22 26 1 0 0 0 0 22 29 1 0 0 0 0 23 16 1 6 0 0 0 23 25 1 0 0 0 0 23 31 1 0 0 0 0 24 27 1 6 0 0 0 24 31 1 0 0 0 0 25 29 2 0 0 0 0 25 32 1 0 0 0 0 26 31 1 0 0 0 0 26 33 2 0 0 0 0 27 30 1 0 0 0 0 27 34 2 0 0 0 0 32 37 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DNC008185; DNCL003578
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	11340891
ChEBI
CAS Number

Drug Properties

Molecular Weight	494.25
ALogP	-1.8
MLogP	3.44
XLogP	3.987
HDA	8
HBD	1
Rotatable Bonds	11
TPSA	108.47
RO5 Violation	0