NPASS drugs

Drug Information

Drug ID:	NPD5265
Drug Name:	Spirapril
Molecular Formula:	C22H30N2O5S2
Canonical SMILES:	CCOC(=O)[C@@H](N[C@H](C(=O)N1CC2(C[C@H]1C(=O)O)SCCS2)C)CCc1ccccc1
Standard InCHI:	InChI=1S/C22H30N2O5S2/c1-3-29-21(28)17(10-9-16-7-5-4-6-8-16)23-15(2)19(25)24-14-22(30-11-12-31-22)13-18(24)20(26)27/h4-8,15,17-18,23H,3,9-14H2,1-2H3,(H,26,27)/t15-,17-,18-/m0/s1
Standard InCHIKey:	HRWCVUIFMSZDJS-SZMVWBNQSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD5265

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	656
0.2-0.3	2943
0.3-0.4	14949
0.4-0.5	10467
0.5-0.6	1406
0.6-0.7	315
0.7-0.8	71
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	0.7733	NPC315266
Intermediate Similarity	0.7718	NPC468984
Intermediate Similarity	0.7647	NPC283783
Intermediate Similarity	0.7635	NPC89489
Intermediate Similarity	0.7616	NPC322878
Intermediate Similarity	0.755	NPC314388
Intermediate Similarity	0.755	NPC315283
Intermediate Similarity	0.755	NPC476978
Intermediate Similarity	0.7517	NPC300315
Intermediate Similarity	0.75	NPC313867
Intermediate Similarity	0.75	NPC316008
Intermediate Similarity	0.7468	NPC105717
Intermediate Similarity	0.7451	NPC314358
Intermediate Similarity	0.7451	NPC262077
Intermediate Similarity	0.7434	NPC52748
Intermediate Similarity	0.7419	NPC2501
Intermediate Similarity	0.7417	NPC263493
Intermediate Similarity	0.7417	NPC269398
Intermediate Similarity	0.741	NPC318930
Intermediate Similarity	0.741	NPC326407
Intermediate Similarity	0.741	NPC317725
Intermediate Similarity	0.741	NPC317362
Intermediate Similarity	0.74	NPC92784
Intermediate Similarity	0.74	NPC178662
Intermediate Similarity	0.74	NPC470884
Intermediate Similarity	0.74	NPC476133
Intermediate Similarity	0.74	NPC98424
Intermediate Similarity	0.7386	NPC209509
Intermediate Similarity	0.7386	NPC5620
Intermediate Similarity	0.7386	NPC471680
Intermediate Similarity	0.7368	NPC161069
Intermediate Similarity	0.7355	NPC240848
Intermediate Similarity	0.7355	NPC471820
Intermediate Similarity	0.7355	NPC471821
Intermediate Similarity	0.7347	NPC130309
Intermediate Similarity	0.7333	NPC471264
Intermediate Similarity	0.7333	NPC471265
Intermediate Similarity	0.7278	NPC122590
Intermediate Similarity	0.7278	NPC286551
Intermediate Similarity	0.7261	NPC7817
Intermediate Similarity	0.7261	NPC475168
Intermediate Similarity	0.7254	NPC302169
Intermediate Similarity	0.7222	NPC6975
Intermediate Similarity	0.7205	NPC297145
Intermediate Similarity	0.7205	NPC197743
Intermediate Similarity	0.7197	NPC129666
Intermediate Similarity	0.7188	NPC469903
Intermediate Similarity	0.7179	NPC138775
Intermediate Similarity	0.7179	NPC329761
Intermediate Similarity	0.7179	NPC225648
Intermediate Similarity	0.7179	NPC145113
Intermediate Similarity	0.7164	NPC67043
Intermediate Similarity	0.7143	NPC77905
Intermediate Similarity	0.7133	NPC200964
Intermediate Similarity	0.7125	NPC470902
Intermediate Similarity	0.7124	NPC239762
Intermediate Similarity	0.7124	NPC163392
Intermediate Similarity	0.7117	NPC469902
Intermediate Similarity	0.7117	NPC469901
Intermediate Similarity	0.7099	NPC324850
Intermediate Similarity	0.7086	NPC4910
Intermediate Similarity	0.7086	NPC248283
Intermediate Similarity	0.7086	NPC141050
Intermediate Similarity	0.7086	NPC329731
Intermediate Similarity	0.7083	NPC71684
Intermediate Similarity	0.7083	NPC202521
Intermediate Similarity	0.7063	NPC473341
Intermediate Similarity	0.7059	NPC132636
Intermediate Similarity	0.7014	NPC476990
Intermediate Similarity	0.7012	NPC471527
Intermediate Similarity	0.7	NPC162104
Remote Similarity	0.6981	NPC13470
Remote Similarity	0.698	NPC473322
Remote Similarity	0.6972	NPC315276
Remote Similarity	0.6972	NPC285926
Remote Similarity	0.6972	NPC14672
Remote Similarity	0.6962	NPC311658
Remote Similarity	0.6959	NPC136453
Remote Similarity	0.6951	NPC1390
Remote Similarity	0.6951	NPC62104
Remote Similarity	0.6946	NPC15068
Remote Similarity	0.6939	NPC222466
Remote Similarity	0.6933	NPC200589
Remote Similarity	0.6923	NPC139326
Remote Similarity	0.6918	NPC252878
Remote Similarity	0.6913	NPC152850
Remote Similarity	0.6913	NPC89923
Remote Similarity	0.6913	NPC71933
Remote Similarity	0.6913	NPC239990
Remote Similarity	0.6913	NPC105114
Remote Similarity	0.6908	NPC287401
Remote Similarity	0.6905	NPC63040
Remote Similarity	0.6892	NPC101719
Remote Similarity	0.6887	NPC255447
Remote Similarity	0.6886	NPC5719
Remote Similarity	0.6886	NPC22883
Remote Similarity	0.6886	NPC217804
Remote Similarity	0.6886	NPC210377
Remote Similarity	0.6883	NPC68865
Remote Similarity	0.6883	NPC127741
Remote Similarity	0.6871	NPC46427
Remote Similarity	0.6871	NPC474082
Remote Similarity	0.6871	NPC175726
Remote Similarity	0.6867	NPC111428
Remote Similarity	0.6864	NPC473000
Remote Similarity	0.6864	NPC469904
Remote Similarity	0.686	NPC469900
Remote Similarity	0.6851	NPC59827
Remote Similarity	0.6851	NPC184933
Remote Similarity	0.6848	NPC469898
Remote Similarity	0.6842	NPC246079
Remote Similarity	0.6839	NPC153554
Remote Similarity	0.6818	NPC314835
Remote Similarity	0.6815	NPC57976
Remote Similarity	0.681	NPC473002
Remote Similarity	0.6807	NPC473003
Remote Similarity	0.6802	NPC477462
Remote Similarity	0.6783	NPC197470
Remote Similarity	0.6779	NPC474847
Remote Similarity	0.6776	NPC157311
Remote Similarity	0.6767	NPC324569
Remote Similarity	0.6744	NPC285622
Remote Similarity	0.6739	NPC477527
Remote Similarity	0.6732	NPC8761
Remote Similarity	0.6732	NPC44805
Remote Similarity	0.6716	NPC322598
Remote Similarity	0.6713	NPC33742
Remote Similarity	0.6709	NPC197682
Remote Similarity	0.669	NPC474584
Remote Similarity	0.669	NPC470545
Remote Similarity	0.6688	NPC46098
Remote Similarity	0.6688	NPC307357
Remote Similarity	0.6688	NPC268841
Remote Similarity	0.6686	NPC63931
Remote Similarity	0.6646	NPC135121
Remote Similarity	0.6646	NPC469427
Remote Similarity	0.6646	NPC469426
Remote Similarity	0.6646	NPC168113
Remote Similarity	0.6644	NPC470546
Remote Similarity	0.6643	NPC35850
Remote Similarity	0.6643	NPC276949
Remote Similarity	0.6642	NPC122493
Remote Similarity	0.6642	NPC10781
Remote Similarity	0.6642	NPC293628
Remote Similarity	0.6629	NPC473001
Remote Similarity	0.6628	NPC475123
Remote Similarity	0.6628	NPC475204
Remote Similarity	0.6627	NPC471051
Remote Similarity	0.6627	NPC471053
Remote Similarity	0.6627	NPC471052
Remote Similarity	0.6625	NPC477217
Remote Similarity	0.6625	NPC201244
Remote Similarity	0.6623	NPC477937
Remote Similarity	0.6621	NPC470544
Remote Similarity	0.6604	NPC176226
Remote Similarity	0.6601	NPC69496
Remote Similarity	0.66	NPC22746
Remote Similarity	0.6592	NPC299806
Remote Similarity	0.6588	NPC472923
Remote Similarity	0.6587	NPC326349
Remote Similarity	0.6587	NPC323336
Remote Similarity	0.6585	NPC300443
Remote Similarity	0.6581	NPC245836
Remote Similarity	0.6581	NPC233910
Remote Similarity	0.6577	NPC169485
Remote Similarity	0.6577	NPC291027
Remote Similarity	0.6577	NPC317474
Remote Similarity	0.6577	NPC213126
Remote Similarity	0.6577	NPC84281
Remote Similarity	0.6575	NPC169328
Remote Similarity	0.6552	NPC137627
Remote Similarity	0.6549	NPC319579
Remote Similarity	0.6545	NPC262166
Remote Similarity	0.6543	NPC83790
Remote Similarity	0.6543	NPC128237
Remote Similarity	0.6533	NPC35996
Remote Similarity	0.6532	NPC46009
Remote Similarity	0.6531	NPC314992
Remote Similarity	0.6531	NPC310467
Remote Similarity	0.6522	NPC164859
Remote Similarity	0.6514	NPC26108
Remote Similarity	0.6507	NPC239357
Remote Similarity	0.6503	NPC329011
Remote Similarity	0.6503	NPC189908
Remote Similarity	0.65	NPC327481
Remote Similarity	0.6497	NPC475318
Remote Similarity	0.6497	NPC90194
Remote Similarity	0.6497	NPC76785
Remote Similarity	0.6497	NPC49577
Remote Similarity	0.6497	NPC260045
Remote Similarity	0.6497	NPC476102
Remote Similarity	0.6497	NPC9687
Remote Similarity	0.6497	NPC474855
Remote Similarity	0.6497	NPC79465
Remote Similarity	0.6497	NPC293377
Remote Similarity	0.6497	NPC474787
Remote Similarity	0.6497	NPC118099
Remote Similarity	0.6497	NPC273907
Remote Similarity	0.6497	NPC474811
Remote Similarity	0.6497	NPC151706

Drug Structure

NPD5265 OpenBabel08211706322D 33 35 0 0 1 0 0 0 0 0999 V2000 8.1230 2.9103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7929 0.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2570 3.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3910 -3.0897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5249 -2.5897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2570 -2.5897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5249 -1.5897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2570 -1.5897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3910 -0.0897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5249 0.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4781 1.0739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9563 0.4158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7929 1.4103 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3910 -1.0897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5249 1.4103 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1473 1.8171 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9268 1.9103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9394 2.7952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3910 1.9103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6589 1.9103 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.0608 1.4103 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.9268 2.9103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6825 3.4644 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0117 3.1042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2570 1.4103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3910 2.9103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 S 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 4.6589 2.9103 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2196 4.0824 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 3 29 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 16 2 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 11 12 1 0 0 0 0 11 30 1 0 0 0 0 12 31 1 0 0 0 0 13 18 1 0 0 0 0 13 22 1 0 0 0 0 14 22 1 0 0 0 0 14 24 1 0 0 0 0 15 2 1 1 0 0 0 15 19 1 0 0 0 0 15 23 1 0 0 0 0 17 10 1 6 0 0 0 17 21 1 0 0 0 0 17 23 1 0 0 0 0 18 20 1 1 0 0 0 18 24 1 0 0 0 0 19 24 1 0 0 0 0 19 25 2 0 0 0 0 20 26 2 0 0 0 0 20 27 1 0 0 0 0 21 28 2 0 0 0 0 21 29 1 0 0 0 0 22 30 1 0 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 27 33 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000911
DrugBank	DB01348
ChEMBL	CHEMBL431
IUPHAR/BPS	6575
PharmaGKB	PA164776913
KEGG Drug
PubChem CID	5311447
ChEBI	135756
CAS Number	83647-97-6

Drug Properties

Molecular Weight	466.16
ALogP	-0.731
MLogP	2.89
XLogP	5.003
HDA	7
HBD	2
Rotatable Bonds	14
TPSA	146.54
RO5 Violation	2