NPASS drugs

Drug Information

Drug ID:	NPD5293
Drug Name:	Piboserod
Molecular Formula:	C22H31N3O2
Canonical SMILES:	CCCCN1CCC(CC1)CNC(=O)c1c2OCCCn2c2c1cccc2
Standard InCHI:	InChI=1S/C22H31N3O2/c1-2-3-11-24-13-9-17(10-14-24)16-23-21(26)20-18-7-4-5-8-19(18)25-12-6-15-27-22(20)25/h4-5,7-8,17H,2-3,6,9-16H2,1H3,(H,23,26)
Standard InCHIKey:	KVCSJPATKXABRQ-UHFFFAOYSA-N
Max Developmental Stage:	Phase 2
Max Developmental Stage Source:	DrugBank

Structural Similarity Between NPASS Natural Products and NPD5293

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	341
0.1-0.2	2102
0.2-0.3	9567
0.3-0.4	4256
0.4-0.5	10752
0.5-0.6	2109
0.6-0.7	1530
0.7-0.8	231
0.8-0.85	2
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	0.8075	NPC472099
Intermediate Similarity	0.8018	NPC478078
Intermediate Similarity	0.7991	NPC323969
Intermediate Similarity	0.7936	NPC157931
Intermediate Similarity	0.79	NPC471762
Intermediate Similarity	0.7873	NPC196718
Intermediate Similarity	0.7873	NPC102593
Intermediate Similarity	0.7854	NPC257851
Intermediate Similarity	0.783	NPC264176
Intermediate Similarity	0.783	NPC472098
Intermediate Similarity	0.782	NPC269367
Intermediate Similarity	0.7818	NPC66777
Intermediate Similarity	0.7818	NPC311906
Intermediate Similarity	0.7804	NPC148183
Intermediate Similarity	0.7804	NPC152768
Intermediate Similarity	0.7767	NPC305984
Intermediate Similarity	0.7762	NPC243850
Intermediate Similarity	0.7736	NPC471304
Intermediate Similarity	0.7685	NPC138370
Intermediate Similarity	0.7679	NPC329631
Intermediate Similarity	0.7674	NPC16066
Intermediate Similarity	0.765	NPC96321
Intermediate Similarity	0.7621	NPC245916
Intermediate Similarity	0.7569	NPC473041
Intermediate Similarity	0.7561	NPC55493
Intermediate Similarity	0.7545	NPC198503
Intermediate Similarity	0.7534	NPC298436
Intermediate Similarity	0.75	NPC184680
Intermediate Similarity	0.7487	NPC28848
Intermediate Similarity	0.7487	NPC14325
Intermediate Similarity	0.7477	NPC122436
Intermediate Similarity	0.7476	NPC329793
Intermediate Similarity	0.7467	NPC101350
Intermediate Similarity	0.7467	NPC470784
Intermediate Similarity	0.7467	NPC470785
Intermediate Similarity	0.7465	NPC277350
Intermediate Similarity	0.7456	NPC477549
Intermediate Similarity	0.7444	NPC21638
Intermediate Similarity	0.7438	NPC282103
Intermediate Similarity	0.7435	NPC475816
Intermediate Similarity	0.7431	NPC477979
Intermediate Similarity	0.7424	NPC235685
Intermediate Similarity	0.7422	NPC194740
Intermediate Similarity	0.7421	NPC128115
Intermediate Similarity	0.7415	NPC102338
Intermediate Similarity	0.7415	NPC63199
Intermediate Similarity	0.7415	NPC196251
Intermediate Similarity	0.7415	NPC111602
Intermediate Similarity	0.7406	NPC295898
Intermediate Similarity	0.7397	NPC322064
Intermediate Similarity	0.7395	NPC475910
Intermediate Similarity	0.7383	NPC472111
Intermediate Similarity	0.7368	NPC473105
Intermediate Similarity	0.7366	NPC97746
Intermediate Similarity	0.7362	NPC91868
Intermediate Similarity	0.7362	NPC63971
Intermediate Similarity	0.7353	NPC133003
Intermediate Similarity	0.7352	NPC50562
Intermediate Similarity	0.7346	NPC241024
Intermediate Similarity	0.7339	NPC310211
Intermediate Similarity	0.7339	NPC308137
Intermediate Similarity	0.733	NPC131885
Intermediate Similarity	0.733	NPC303658
Intermediate Similarity	0.7327	NPC123839
Intermediate Similarity	0.7325	NPC473186
Intermediate Similarity	0.7325	NPC474192
Intermediate Similarity	0.7325	NPC475720
Intermediate Similarity	0.7322	NPC478083
Intermediate Similarity	0.7318	NPC67658
Intermediate Similarity	0.7317	NPC141612
Intermediate Similarity	0.7317	NPC17273
Intermediate Similarity	0.7317	NPC194040
Intermediate Similarity	0.7317	NPC66210
Intermediate Similarity	0.7317	NPC135601
Intermediate Similarity	0.7316	NPC474183
Intermediate Similarity	0.7315	NPC287208
Intermediate Similarity	0.7311	NPC329747
Intermediate Similarity	0.7311	NPC214428
Intermediate Similarity	0.7308	NPC472113
Intermediate Similarity	0.7306	NPC151781
Intermediate Similarity	0.7306	NPC74562
Intermediate Similarity	0.7306	NPC316181
Intermediate Similarity	0.7304	NPC473187
Intermediate Similarity	0.7302	NPC45190
Intermediate Similarity	0.7297	NPC168209
Intermediate Similarity	0.7295	NPC45389
Intermediate Similarity	0.7294	NPC146418
Intermediate Similarity	0.7281	NPC174672
Intermediate Similarity	0.7281	NPC260434
Intermediate Similarity	0.728	NPC303374
Intermediate Similarity	0.7277	NPC471944
Intermediate Similarity	0.7269	NPC249583
Intermediate Similarity	0.7269	NPC270918
Intermediate Similarity	0.7265	NPC150239
Intermediate Similarity	0.7261	NPC39370
Intermediate Similarity	0.7252	NPC46561
Intermediate Similarity	0.7249	NPC49547
Intermediate Similarity	0.7235	NPC82548
Intermediate Similarity	0.7235	NPC266249
Intermediate Similarity	0.7232	NPC280799
Intermediate Similarity	0.7222	NPC196449
Intermediate Similarity	0.7222	NPC300156
Intermediate Similarity	0.7222	NPC314222
Intermediate Similarity	0.7222	NPC82053
Intermediate Similarity	0.722	NPC74360
Intermediate Similarity	0.722	NPC288987
Intermediate Similarity	0.722	NPC258480
Intermediate Similarity	0.722	NPC472119
Intermediate Similarity	0.7212	NPC473449
Intermediate Similarity	0.7212	NPC472112
Intermediate Similarity	0.7209	NPC41216
Intermediate Similarity	0.7207	NPC169402
Intermediate Similarity	0.7204	NPC472116
Intermediate Similarity	0.7202	NPC174758
Intermediate Similarity	0.72	NPC243633
Intermediate Similarity	0.72	NPC478141
Intermediate Similarity	0.72	NPC175150
Intermediate Similarity	0.72	NPC220851
Intermediate Similarity	0.7198	NPC278434
Intermediate Similarity	0.7195	NPC116238
Intermediate Similarity	0.7189	NPC193238
Intermediate Similarity	0.7189	NPC4687
Intermediate Similarity	0.7184	NPC472107
Intermediate Similarity	0.7184	NPC79062
Intermediate Similarity	0.7178	NPC53534
Intermediate Similarity	0.7178	NPC84347
Intermediate Similarity	0.7177	NPC92111
Intermediate Similarity	0.7175	NPC247803
Intermediate Similarity	0.7168	NPC205372
Intermediate Similarity	0.7167	NPC329982
Intermediate Similarity	0.7167	NPC244543
Intermediate Similarity	0.7163	NPC474116
Intermediate Similarity	0.7163	NPC162730
Intermediate Similarity	0.7162	NPC469928
Intermediate Similarity	0.715	NPC312870
Intermediate Similarity	0.715	NPC311858
Intermediate Similarity	0.715	NPC199851
Intermediate Similarity	0.715	NPC294909
Intermediate Similarity	0.715	NPC128265
Intermediate Similarity	0.715	NPC254240
Intermediate Similarity	0.7149	NPC74575
Intermediate Similarity	0.7149	NPC471080
Intermediate Similarity	0.7149	NPC478081
Intermediate Similarity	0.7149	NPC469592
Intermediate Similarity	0.7136	NPC114637
Intermediate Similarity	0.713	NPC217176
Intermediate Similarity	0.7129	NPC76748
Intermediate Similarity	0.7129	NPC329858
Intermediate Similarity	0.7129	NPC314333
Intermediate Similarity	0.7124	NPC6786
Intermediate Similarity	0.7124	NPC216612
Intermediate Similarity	0.7124	NPC240384
Intermediate Similarity	0.7123	NPC469589
Intermediate Similarity	0.7119	NPC142385
Intermediate Similarity	0.7119	NPC316224
Intermediate Similarity	0.7119	NPC188400
Intermediate Similarity	0.7113	NPC26872
Intermediate Similarity	0.7112	NPC253675
Intermediate Similarity	0.711	NPC53344
Intermediate Similarity	0.7109	NPC198673
Intermediate Similarity	0.7109	NPC307963
Intermediate Similarity	0.7106	NPC477066
Intermediate Similarity	0.7093	NPC322482
Intermediate Similarity	0.7092	NPC26850
Intermediate Similarity	0.7091	NPC470020
Intermediate Similarity	0.709	NPC191489
Intermediate Similarity	0.7089	NPC81939
Intermediate Similarity	0.7087	NPC470205
Intermediate Similarity	0.7087	NPC176127
Intermediate Similarity	0.7085	NPC330009
Intermediate Similarity	0.7081	NPC175474
Intermediate Similarity	0.7081	NPC296527
Intermediate Similarity	0.708	NPC60621
Intermediate Similarity	0.7078	NPC171787
Intermediate Similarity	0.7076	NPC478082
Intermediate Similarity	0.7076	NPC477067
Intermediate Similarity	0.7076	NPC72905
Intermediate Similarity	0.7075	NPC230313
Intermediate Similarity	0.7075	NPC19692
Intermediate Similarity	0.7075	NPC220151
Intermediate Similarity	0.7074	NPC140296
Intermediate Similarity	0.7064	NPC315638
Intermediate Similarity	0.7064	NPC313796
Intermediate Similarity	0.7064	NPC313345
Intermediate Similarity	0.7064	NPC314855
Intermediate Similarity	0.7059	NPC187501
Intermediate Similarity	0.7059	NPC87413
Intermediate Similarity	0.7059	NPC283152
Intermediate Similarity	0.7059	NPC475666
Intermediate Similarity	0.7056	NPC168911
Intermediate Similarity	0.7056	NPC474916
Intermediate Similarity	0.7053	NPC477003
Intermediate Similarity	0.7053	NPC21429
Intermediate Similarity	0.7053	NPC84478
Intermediate Similarity	0.7051	NPC477587
Intermediate Similarity	0.7051	NPC477589
Intermediate Similarity	0.7048	NPC324091
Intermediate Similarity	0.7046	NPC75179
Intermediate Similarity	0.7045	NPC88923
Intermediate Similarity	0.7045	NPC315634

Drug Structure

NPD5293 OpenBabel08211706322D 28 31 0 0 0 0 0 0 0 0999 V2000 -2.5981 1.5000 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5906 -1.6053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1839 -2.5188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0872 -2.0699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0028 -0.7963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8106 -2.6234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1361 -2.3790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 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 4.2951 -1.0918 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9917 -0.9008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3984 -1.8143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7348 -0.2317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6009 -0.7317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 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 2.3930 -1.7098 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5519 -0.4227 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 11 1 0 0 0 0 4 5 2 0 0 0 0 4 7 1 0 0 0 0 5 8 1 0 0 0 0 6 12 1 0 0 0 0 6 15 1 0 0 0 0 7 18 2 0 0 0 0 8 19 2 0 0 0 0 9 13 1 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 10 17 1 0 0 0 0 11 24 1 0 0 0 0 12 25 1 0 0 0 0 13 24 1 0 0 0 0 14 24 1 0 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 16 23 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 25 1 0 0 0 0 20 21 1 0 0 0 0 20 22 2 0 0 0 0 21 23 1 0 0 0 0 21 26 2 0 0 0 0 22 25 1 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DNC001122; DCL000545; DNC001295
DrugBank	DB04873
ChEMBL	CHEMBL356359
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	177335; 177336
ChEBI
CAS Number	152811-62-6

Drug Properties

Molecular Weight	369.24
ALogP	-2.3877
MLogP	3.33
XLogP	3.861
HDA	4
HBD	1
Rotatable Bonds	8
TPSA	46.5
RO5 Violation	0