NPASS drugs

Drug Information

Drug ID:	NPD8358
Drug Name:	Voacamine
Molecular Formula:	C43H52N4O5
Canonical SMILES:	COC(=O)C1[C@H]2C[C@H](c3cc4[nH]c5c(c4cc3OC)CCN3[C@@H]4[C@]5(C[C@H](C[C@@H]4CC)C3)C(=O)OC)c3c(C[C@H]1N(C/C/2=C/C)C)c1ccccc1[nH]3
Standard InCHI:	"InChI=1S/C43H52N4O5/c1-7-24-15-23-20-43(42(49)52-6)39-27(13-14-47(21-23)40(24)43)29-19-36(50-4)30(17-34(29)45-39)31-16-28-25(8-2)22-46(3)35(37(28)41(48)51-5)18-32-26-11-9-10-12-33(26)44-38(31)32/h8-12,17,19,23-24,28,31,35,37,40,44-45H,7,13-16,18,20-22H2,1-6H3/b25-8-/t23-,24-,28-,31+,35+,37?,40-,43+/m0/s1"
Standard InCHIKey:	VCMIRXRRQJNZJT-XRMSBCOFSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	DrugBank

Structural Similarity Between NPASS Natural Products and NPD8358

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.
Tanimoto coefficient is calculated based on PubChem 881-bit substructure fingerprints.

Range	Similarity Score Range
0-0.1	109114
0.1-0.2	99615
0.2-0.3	2502
0.3-0.4	311
0.4-0.5	83
0.5-0.6	57
0.6-0.7	24
0.7-0.8	10
0.8-0.85	9
0.85-0.9	4
0.9-0.95	0
0.95-1	4

Similar Natural Products

High Similarity: Tc>=0.85; Intermediate Similarity: 0.7 <= Tc < 0.85; Remote Similarity: 0.5 <= Tc < 0.7

Similarity Level	Similarity Score	Natural Product ID
High Similarity	1.0	NPC41549
High Similarity	1.0	NPC513478
High Similarity	1.0	NPC516036
High Similarity	1.0	NPC596897
High Similarity	0.8981	NPC507778
High Similarity	0.8981	NPC510580
High Similarity	0.8624	NPC28112
High Similarity	0.8624	NPC591898
Intermediate Similarity	0.8411	NPC522567
Intermediate Similarity	0.8318	NPC17437
Intermediate Similarity	0.8318	NPC517840
Intermediate Similarity	0.8318	NPC540496
Intermediate Similarity	0.8198	NPC92670
Intermediate Similarity	0.8198	NPC485922
Intermediate Similarity	0.8198	NPC530372
Intermediate Similarity	0.8036	NPC506861
Intermediate Similarity	0.8	NPC582516
Intermediate Similarity	0.7838	NPC294231
Intermediate Similarity	0.7838	NPC526113
Intermediate Similarity	0.7719	NPC528756
Intermediate Similarity	0.7632	NPC485921
Intermediate Similarity	0.7632	NPC478082
Intermediate Similarity	0.7632	NPC477067
Intermediate Similarity	0.7217	NPC475666
Intermediate Similarity	0.7203	NPC485889
Intermediate Similarity	0.713	NPC485933
Intermediate Similarity	0.713	NPC485970
Remote Similarity	0.6903	NPC485963
Remote Similarity	0.681	NPC485969
Remote Similarity	0.681	NPC494267
Remote Similarity	0.681	NPC567055
Remote Similarity	0.678	NPC81939
Remote Similarity	0.6777	NPC508255
Remote Similarity	0.6508	NPC488883
Remote Similarity	0.6393	NPC485893
Remote Similarity	0.6393	NPC514981
Remote Similarity	0.6333	NPC29422
Remote Similarity	0.6333	NPC569124
Remote Similarity	0.625	NPC485894
Remote Similarity	0.625	NPC477066
Remote Similarity	0.622	NPC488882
Remote Similarity	0.622	NPC485918
Remote Similarity	0.622	NPC485915
Remote Similarity	0.6179	NPC485966
Remote Similarity	0.6179	NPC511898
Remote Similarity	0.6154	NPC485917
Remote Similarity	0.6154	NPC485954
Remote Similarity	0.6142	NPC563182
Remote Similarity	0.6139	NPC329858
Remote Similarity	0.6139	NPC170271
Remote Similarity	0.6139	NPC571862
Remote Similarity	0.5984	NPC485913
Remote Similarity	0.5968	NPC485897
Remote Similarity	0.5968	NPC485896
Remote Similarity	0.5968	NPC485890
Remote Similarity	0.5954	NPC166104
Remote Similarity	0.5954	NPC207884
Remote Similarity	0.5954	NPC596314
Remote Similarity	0.5954	NPC597230
Remote Similarity	0.5952	NPC485885
Remote Similarity	0.5938	NPC485892
Remote Similarity	0.5878	NPC485935
Remote Similarity	0.5859	NPC42185
Remote Similarity	0.5859	NPC507118
Remote Similarity	0.5854	NPC485964
Remote Similarity	0.5846	NPC478083
Remote Similarity	0.5814	NPC485953
Remote Similarity	0.5802	NPC478080
Remote Similarity	0.5682	NPC188604
Remote Similarity	0.5682	NPC119459
Remote Similarity	0.5682	NPC62132
Remote Similarity	0.5682	NPC504253
Remote Similarity	0.5682	NPC531327
Remote Similarity	0.5682	NPC573070
Remote Similarity	0.5682	NPC605382
Remote Similarity	0.566	NPC96321
Remote Similarity	0.566	NPC111993
Remote Similarity	0.566	NPC134263
Remote Similarity	0.566	NPC609507
Remote Similarity	0.5659	NPC485886
Remote Similarity	0.56	NPC551619
Remote Similarity	0.5566	NPC482061
Remote Similarity	0.5556	NPC485945
Remote Similarity	0.5481	NPC485943
Remote Similarity	0.5441	NPC485919
Remote Similarity	0.5441	NPC485920
Remote Similarity	0.5433	NPC269708
Remote Similarity	0.5421	NPC473041
Remote Similarity	0.5421	NPC570346
Remote Similarity	0.5379	NPC478081
Remote Similarity	0.537	NPC187357
Remote Similarity	0.537	NPC485936
Remote Similarity	0.537	NPC485937
Remote Similarity	0.537	NPC532483
Remote Similarity	0.537	NPC555231
Remote Similarity	0.537	NPC558854
Remote Similarity	0.537	NPC572358
Remote Similarity	0.5259	NPC8809
Remote Similarity	0.5255	NPC471303
Remote Similarity	0.5185	NPC560572
Remote Similarity	0.5182	NPC526319
Remote Similarity	0.5149	NPC485960
Remote Similarity	0.5135	NPC505991
Remote Similarity	0.5109	NPC485912
Remote Similarity	0.5079	NPC485962
Remote Similarity	0.5079	NPC477065
Remote Similarity	0.5071	NPC96778
Remote Similarity	0.5071	NPC516526

Drug Structure

NPD8358 OpenBabel08211713012D 54 62 0 0 1 0 0 0 0 0999 V2000 2.1816 0.5745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6518 4.8426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4564 3.6300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3134 5.1259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7422 7.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8721 -2.0386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0771 -0.4200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4823 4.2855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4986 1.2623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8048 0.5421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2218 2.2232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8342 0.7828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7575 1.6350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0150 0.9999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0741 -1.2475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8013 4.7285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1783 2.2066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3532 4.1661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4031 3.1279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4255 -1.1023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0120 -0.8018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0267 4.2182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6464 -1.2924 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1635 -0.8268 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3800 4.7261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2512 2.4639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7356 1.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3738 5.5484 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4480 2.1289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1334 3.2056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9761 3.7439 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7806 3.3463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5574 1.7437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3356 1.6682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1783 5.1507 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2458 3.6662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3584 5.7233 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.7960 3.1714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1829 0.5327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7911 -0.6117 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5736 6.6998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7605 -0.3102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7626 -0.3746 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6581 2.1809 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.1717 0.6818 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.8270 4.4072 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 5.8355 7.3745 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2036 0.5863 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2010 4.6652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5270 7.0017 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3153 -1.1422 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7757 1.7104 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8735 -0.0306 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 8 1 0 0 0 0 3 46 1 0 0 0 0 4 50 1 0 0 0 0 5 51 1 0 0 0 0 6 52 1 0 0 0 0 8 25 2 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 26 2 0 0 0 0 12 33 2 0 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 14 47 1 0 0 0 0 15 24 1 0 0 0 0 16 31 1 0 0 0 0 17 30 1 0 0 0 0 17 34 2 0 0 0 0 18 32 1 0 0 0 0 19 29 2 0 0 0 0 19 36 1 0 0 0 0 20 23 1 0 0 0 0 20 43 1 0 0 0 0 21 23 1 0 0 0 0 21 47 1 0 0 0 0 22 25 1 0 0 0 0 22 46 1 0 0 0 0 23 15 1 6 0 0 0 24 7 1 1 0 0 0 24 40 1 0 0 0 0 25 28 1 0 0 0 0 26 32 1 0 0 0 0 26 33 1 0 0 0 0 27 29 1 0 0 0 0 27 39 2 0 0 0 0 28 16 1 6 0 0 0 28 37 1 0 0 0 0 29 34 1 0 0 0 0 30 36 2 0 0 0 0 31 30 1 1 0 0 0 31 38 1 0 0 0 0 32 38 2 0 0 0 0 33 44 1 0 0 0 0 34 45 1 0 0 0 0 35 18 1 1 0 0 0 35 37 1 0 0 0 0 35 46 1 0 0 0 0 36 50 1 0 0 0 0 37 41 1 0 0 0 0 38 44 1 0 0 0 0 39 43 1 0 0 0 0 39 45 1 0 0 0 0 40 43 1 1 0 0 0 40 47 1 0 0 0 0 41 48 2 0 0 0 0 41 51 1 0 0 0 0 42 49 2 0 0 0 0 42 52 1 0 0 0 0 43 42 1 1 0 0 0 44 53 1 0 0 0 0 45 54 1 0 0 0 0 M END $$$$

External Identifiers

TTD
DrugBank	DB04877
ChEMBL	CHEMBL445022
IUPHAR/BPS
PharmaGKB	PA165958347
KEGG Drug
PubChem CID	0
ChEBI
CAS Number	3371-85-5

Drug Properties

Molecular Weight	704.39
ALogP	-0.7638
MLogP	5.2
XLogP	5.817
HDA	8
HBD	2
Rotatable Bonds	13
TPSA	99.89
RO5 Violation	1