NPASS drugs

Drug Information

Drug ID:	NPD5296
Drug Name:	Cilazapril
Molecular Formula:	C22H31N3O5
Canonical SMILES:	CCOC(=O)[C@@H](N[C@H]1CCCN2N(C1=O)[C@@H](CCC2)C(=O)O)CCc1ccccc1
Standard InCHI:	InChI=1S/C22H31N3O5/c1-2-30-22(29)18(13-12-16-8-4-3-5-9-16)23-17-10-6-14-24-15-7-11-19(21(27)28)25(24)20(17)26/h3-5,8-9,17-19,23H,2,6-7,10-15H2,1H3,(H,27,28)/t17-,18-,19-/m0/s1
Standard InCHIKey:	HHHKFGXWKKUNCY-FHWLQOOXSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD5296

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	83
0.1-0.2	561
0.2-0.3	2311
0.3-0.4	11301
0.4-0.5	14252
0.5-0.6	1953
0.6-0.7	326
0.7-0.8	103
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	0.7762	NPC163392
Intermediate Similarity	0.7762	NPC239762
Intermediate Similarity	0.7667	NPC473341
Intermediate Similarity	0.7619	NPC67043
Intermediate Similarity	0.7532	NPC1390
Intermediate Similarity	0.7532	NPC62104
Intermediate Similarity	0.75	NPC71684
Intermediate Similarity	0.7484	NPC471527
Intermediate Similarity	0.7448	NPC132636
Intermediate Similarity	0.7432	NPC315266
Intermediate Similarity	0.7432	NPC209509
Intermediate Similarity	0.7415	NPC161069
Intermediate Similarity	0.7365	NPC52748
Intermediate Similarity	0.7357	NPC136453
Intermediate Similarity	0.7351	NPC2501
Intermediate Similarity	0.7347	NPC263493
Intermediate Similarity	0.7347	NPC269398
Intermediate Similarity	0.7342	NPC5719
Intermediate Similarity	0.7342	NPC210377
Intermediate Similarity	0.7342	NPC217804
Intermediate Similarity	0.7342	NPC22883
Intermediate Similarity	0.7329	NPC470884
Intermediate Similarity	0.7329	NPC178662
Intermediate Similarity	0.7329	NPC92784
Intermediate Similarity	0.7329	NPC98424
Intermediate Similarity	0.7329	NPC476133
Intermediate Similarity	0.732	NPC122590
Intermediate Similarity	0.7315	NPC5620
Intermediate Similarity	0.7305	NPC89923
Intermediate Similarity	0.7305	NPC152850
Intermediate Similarity	0.7305	NPC105114
Intermediate Similarity	0.7305	NPC71933
Intermediate Similarity	0.7305	NPC239990
Intermediate Similarity	0.7296	NPC15068
Intermediate Similarity	0.7285	NPC471821
Intermediate Similarity	0.7285	NPC471820
Intermediate Similarity	0.7267	NPC262077
Intermediate Similarity	0.726	NPC471265
Intermediate Similarity	0.726	NPC471264
Intermediate Similarity	0.726	NPC127741
Intermediate Similarity	0.7254	NPC111428
Intermediate Similarity	0.725	NPC63040
Intermediate Similarity	0.7248	NPC315283
Intermediate Similarity	0.7248	NPC314388
Intermediate Similarity	0.7248	NPC476978
Intermediate Similarity	0.7219	NPC138775
Intermediate Similarity	0.7214	NPC222466
Intermediate Similarity	0.72	NPC324569
Intermediate Similarity	0.72	NPC313867
Intermediate Similarity	0.72	NPC316008
Intermediate Similarity	0.7192	NPC314835
Intermediate Similarity	0.719	NPC7817
Intermediate Similarity	0.719	NPC475168
Intermediate Similarity	0.7185	NPC197470
Intermediate Similarity	0.7181	NPC139326
Intermediate Similarity	0.7163	NPC101719
Intermediate Similarity	0.7153	NPC157311
Intermediate Similarity	0.7152	NPC314358
Intermediate Similarity	0.7152	NPC314114
Intermediate Similarity	0.7143	NPC6975
Intermediate Similarity	0.7143	NPC68865
Intermediate Similarity	0.7134	NPC197743
Intermediate Similarity	0.7134	NPC297145
Intermediate Similarity	0.7124	NPC129666
Intermediate Similarity	0.7113	NPC477937
Intermediate Similarity	0.7111	NPC33742
Intermediate Similarity	0.7105	NPC329761
Intermediate Similarity	0.7105	NPC225648
Intermediate Similarity	0.7105	NPC145113
Intermediate Similarity	0.7103	NPC44805
Intermediate Similarity	0.7103	NPC8761
Intermediate Similarity	0.7103	NPC246079
Intermediate Similarity	0.709	NPC474584
Intermediate Similarity	0.708	NPC470545
Intermediate Similarity	0.7077	NPC473418
Intermediate Similarity	0.7068	NPC319579
Intermediate Similarity	0.7063	NPC122493
Intermediate Similarity	0.7063	NPC471053
Intermediate Similarity	0.7063	NPC293628
Intermediate Similarity	0.7063	NPC10781
Intermediate Similarity	0.7063	NPC471051
Intermediate Similarity	0.7063	NPC471052
Intermediate Similarity	0.7059	NPC240848
Intermediate Similarity	0.7055	NPC46009
Intermediate Similarity	0.7051	NPC470902
Intermediate Similarity	0.705	NPC200964
Intermediate Similarity	0.7042	NPC474847
Intermediate Similarity	0.7037	NPC276949
Intermediate Similarity	0.7037	NPC35850
Intermediate Similarity	0.7034	NPC130309
Intermediate Similarity	0.7029	NPC470546
Intermediate Similarity	0.7021	NPC35996
Intermediate Similarity	0.7014	NPC473322
Intermediate Similarity	0.7014	NPC469666
Intermediate Similarity	0.7008	NPC322598
Intermediate Similarity	0.7007	NPC14672
Intermediate Similarity	0.7007	NPC315276
Intermediate Similarity	0.7007	NPC470544
Intermediate Similarity	0.7007	NPC474473
Intermediate Similarity	0.7007	NPC285926
Intermediate Similarity	0.7007	NPC248283
Intermediate Similarity	0.7006	NPC469903
Intermediate Similarity	0.7	NPC202521
Remote Similarity	0.697	NPC306804
Remote Similarity	0.6957	NPC169328
Remote Similarity	0.6954	NPC57976
Remote Similarity	0.6954	NPC197682
Remote Similarity	0.6948	NPC105717
Remote Similarity	0.6937	NPC469902
Remote Similarity	0.6933	NPC46098
Remote Similarity	0.6933	NPC268841
Remote Similarity	0.6933	NPC307357
Remote Similarity	0.6929	NPC476990
Remote Similarity	0.6929	NPC302169
Remote Similarity	0.6923	NPC162104
Remote Similarity	0.6923	NPC164859
Remote Similarity	0.6923	NPC300443
Remote Similarity	0.6918	NPC324850
Remote Similarity	0.6918	NPC255447
Remote Similarity	0.6906	NPC310467
Remote Similarity	0.6906	NPC314992
Remote Similarity	0.6901	NPC474082
Remote Similarity	0.6901	NPC175726
Remote Similarity	0.6894	NPC327481
Remote Similarity	0.6889	NPC329011
Remote Similarity	0.6887	NPC469427
Remote Similarity	0.6887	NPC469426
Remote Similarity	0.6887	NPC168113
Remote Similarity	0.6883	NPC311658
Remote Similarity	0.6883	NPC135121
Remote Similarity	0.6863	NPC477217
Remote Similarity	0.6863	NPC201244
Remote Similarity	0.6853	NPC22746
Remote Similarity	0.6849	NPC69496
Remote Similarity	0.6848	NPC475123
Remote Similarity	0.6848	NPC475204
Remote Similarity	0.6842	NPC77905
Remote Similarity	0.6842	NPC176226
Remote Similarity	0.6832	NPC469901
Remote Similarity	0.6831	NPC84281
Remote Similarity	0.6831	NPC252878
Remote Similarity	0.6831	NPC291027
Remote Similarity	0.6831	NPC213126
Remote Similarity	0.6831	NPC169485
Remote Similarity	0.6831	NPC317474
Remote Similarity	0.6824	NPC245836
Remote Similarity	0.6824	NPC473404
Remote Similarity	0.6824	NPC233910
Remote Similarity	0.6805	NPC269750
Remote Similarity	0.6805	NPC194671
Remote Similarity	0.679	NPC73655
Remote Similarity	0.6783	NPC46427
Remote Similarity	0.6781	NPC311753
Remote Similarity	0.6779	NPC141050
Remote Similarity	0.6772	NPC286551
Remote Similarity	0.6766	NPC137627
Remote Similarity	0.6766	NPC285622
Remote Similarity	0.6766	NPC273755
Remote Similarity	0.6763	NPC2265
Remote Similarity	0.6763	NPC239357
Remote Similarity	0.6757	NPC257390
Remote Similarity	0.6747	NPC276506
Remote Similarity	0.6743	NPC240130
Remote Similarity	0.6743	NPC61332
Remote Similarity	0.6741	NPC158854
Remote Similarity	0.6735	NPC200589
Remote Similarity	0.6728	NPC475544
Remote Similarity	0.6727	NPC107938
Remote Similarity	0.6727	NPC294516
Remote Similarity	0.6726	NPC155506
Remote Similarity	0.6726	NPC476227
Remote Similarity	0.6726	NPC159767
Remote Similarity	0.6726	NPC279871
Remote Similarity	0.6723	NPC314083
Remote Similarity	0.6712	NPC319766
Remote Similarity	0.6711	NPC476259
Remote Similarity	0.6707	NPC63931
Remote Similarity	0.6692	NPC12730
Remote Similarity	0.669	NPC27833
Remote Similarity	0.669	NPC190663
Remote Similarity	0.669	NPC80150
Remote Similarity	0.669	NPC4974
Remote Similarity	0.6687	NPC469904
Remote Similarity	0.6687	NPC473580
Remote Similarity	0.6686	NPC50016
Remote Similarity	0.6667	NPC237420
Remote Similarity	0.6667	NPC24617
Remote Similarity	0.6647	NPC274198
Remote Similarity	0.6647	NPC198254
Remote Similarity	0.6647	NPC40234
Remote Similarity	0.6645	NPC77992
Remote Similarity	0.6645	NPC322878
Remote Similarity	0.6644	NPC65310
Remote Similarity	0.6629	NPC302715
Remote Similarity	0.6627	NPC477462
Remote Similarity	0.6627	NPC473354
Remote Similarity	0.6626	NPC114806
Remote Similarity	0.6626	NPC473003
Remote Similarity	0.6626	NPC469243
Remote Similarity	0.6625	NPC473002

Drug Structure

NPD5296 OpenBabel08211706322D 32 34 0 0 1 0 0 0 0 0999 V2000 4.5876 -4.4088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7216 -3.9088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4536 0.0912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4536 -0.9088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5876 0.5912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2470 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7307 1.8617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5876 -1.4088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7216 0.0912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0245 -0.9749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3542 1.0799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8555 -1.4088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8555 -2.4088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6235 0.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2581 1.7127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7216 -0.9088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1235 -1.4088 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9895 -2.9088 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9888 0.1490 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2225 -0.9749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6123 -0.6328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9895 -3.9088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1235 -2.4088 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6235 0.7818 0.0000 N 0 0 3 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 -0.5593 -1.5984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2470 -1.5637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6012 -0.4837 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1235 -4.4088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8555 -4.4088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2575 -2.9088 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9665 0.4471 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 30 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 8 1 0 0 0 0 5 9 2 0 0 0 0 6 10 1 0 0 0 0 6 14 1 0 0 0 0 7 11 1 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 16 1 0 0 0 0 14 24 1 0 0 0 0 15 24 1 0 0 0 0 17 20 1 0 0 0 0 17 23 1 6 0 0 0 18 13 1 1 0 0 0 18 22 1 0 0 0 0 18 23 1 0 0 0 0 19 21 1 6 0 0 0 19 25 1 0 0 0 0 20 25 1 0 0 0 0 20 26 2 0 0 0 0 21 27 2 0 0 0 0 21 28 1 0 0 0 0 22 29 2 0 0 0 0 22 30 1 0 0 0 0 23 31 1 0 0 0 0 24 25 1 0 0 0 0 28 32 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000912
DrugBank	DB01340
ChEMBL	CHEMBL515606
IUPHAR/BPS	6459
PharmaGKB	PA164748302
KEGG Drug	D07699
PubChem CID	56330
ChEBI	3698
CAS Number	88768-40-5

Drug Properties

Molecular Weight	417.23
ALogP	-2.8459
MLogP	3
XLogP	4.186
HDA	8
HBD	2
Rotatable Bonds	11
TPSA	99.18
RO5 Violation	0