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 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	435
0.1-0.2	1897
0.2-0.3	8539
0.3-0.4	6255
0.4-0.5	10197
0.5-0.6	2113
0.6-0.7	1206
0.7-0.8	221
0.8-0.85	13
0.85-0.9	4
0.9-0.95	5
0.95-1	5

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
High Similarity	1.0	NPC17437
High Similarity	0.9816	NPC477067
High Similarity	0.9816	NPC478082
High Similarity	0.9679	NPC477066
High Similarity	0.9635	NPC478081
High Similarity	0.9469	NPC478080
High Similarity	0.9372	NPC81939
High Similarity	0.933	NPC475666
High Similarity	0.9283	NPC473540
High Similarity	0.9091	NPC478083
High Similarity	0.8894	NPC96321
High Similarity	0.8705	NPC311906
High Similarity	0.8509	NPC474192
High Similarity	0.8509	NPC475720
Intermediate Similarity	0.8496	NPC471303
Intermediate Similarity	0.8486	NPC471304
Intermediate Similarity	0.8468	NPC473041
Intermediate Similarity	0.8378	NPC469928
Intermediate Similarity	0.8368	NPC329982
Intermediate Similarity	0.8349	NPC477065
Intermediate Similarity	0.8291	NPC475816
Intermediate Similarity	0.8288	NPC478074
Intermediate Similarity	0.8174	NPC478078
Intermediate Similarity	0.8157	NPC329793
Intermediate Similarity	0.8155	NPC473105
Intermediate Similarity	0.8053	NPC152768
Intermediate Similarity	0.8053	NPC148183
Intermediate Similarity	0.7991	NPC472099
Intermediate Similarity	0.7974	NPC330009
Intermediate Similarity	0.794	NPC470126
Intermediate Similarity	0.792	NPC472098
Intermediate Similarity	0.7906	NPC253580
Intermediate Similarity	0.7802	NPC280799
Intermediate Similarity	0.7782	NPC195788
Intermediate Similarity	0.7782	NPC237901
Intermediate Similarity	0.7748	NPC329747
Intermediate Similarity	0.7746	NPC469734
Intermediate Similarity	0.7742	NPC329858
Intermediate Similarity	0.7733	NPC300156
Intermediate Similarity	0.7719	NPC208284
Intermediate Similarity	0.7706	NPC305984
Intermediate Similarity	0.7702	NPC21638
Intermediate Similarity	0.7665	NPC475910
Intermediate Similarity	0.7663	NPC260909
Intermediate Similarity	0.7632	NPC476116
Intermediate Similarity	0.7617	NPC280272
Intermediate Similarity	0.76	NPC162730
Intermediate Similarity	0.7593	NPC39370
Intermediate Similarity	0.7583	NPC473186
Intermediate Similarity	0.758	NPC314333
Intermediate Similarity	0.7579	NPC284685
Intermediate Similarity	0.7572	NPC41679
Intermediate Similarity	0.7563	NPC157931
Intermediate Similarity	0.7549	NPC191489
Intermediate Similarity	0.7542	NPC477531
Intermediate Similarity	0.7532	NPC477533
Intermediate Similarity	0.7532	NPC473180
Intermediate Similarity	0.7532	NPC94157
Intermediate Similarity	0.7531	NPC33949
Intermediate Similarity	0.7531	NPC252251
Intermediate Similarity	0.7531	NPC314954
Intermediate Similarity	0.7522	NPC474116
Intermediate Similarity	0.75	NPC88923
Intermediate Similarity	0.75	NPC209174
Intermediate Similarity	0.75	NPC315634
Intermediate Similarity	0.75	NPC100734
Intermediate Similarity	0.75	NPC45190
Intermediate Similarity	0.7469	NPC475253
Intermediate Similarity	0.7457	NPC475778
Intermediate Similarity	0.7448	NPC227908
Intermediate Similarity	0.7436	NPC183407
Intermediate Similarity	0.7434	NPC249040
Intermediate Similarity	0.7418	NPC473187
Intermediate Similarity	0.7418	NPC295228
Intermediate Similarity	0.7404	NPC476041
Intermediate Similarity	0.7404	NPC304926
Intermediate Similarity	0.7404	NPC169402
Intermediate Similarity	0.7391	NPC4687
Intermediate Similarity	0.7384	NPC86078
Intermediate Similarity	0.7373	NPC46561
Intermediate Similarity	0.7371	NPC126066
Intermediate Similarity	0.7371	NPC234999
Intermediate Similarity	0.7366	NPC131017
Intermediate Similarity	0.7362	NPC170114
Intermediate Similarity	0.7354	NPC55493
Intermediate Similarity	0.7353	NPC477532
Intermediate Similarity	0.7344	NPC473185
Intermediate Similarity	0.7344	NPC6215
Intermediate Similarity	0.7341	NPC133609
Intermediate Similarity	0.7336	NPC162484
Intermediate Similarity	0.7336	NPC223427
Intermediate Similarity	0.7328	NPC201697
Intermediate Similarity	0.7322	NPC144452
Intermediate Similarity	0.7319	NPC470549
Intermediate Similarity	0.7319	NPC116238
Intermediate Similarity	0.7317	NPC15801
Intermediate Similarity	0.7317	NPC184680
Intermediate Similarity	0.7316	NPC193777
Intermediate Similarity	0.7312	NPC189079
Intermediate Similarity	0.7311	NPC132642
Intermediate Similarity	0.7306	NPC176127
Intermediate Similarity	0.73	NPC303658
Intermediate Similarity	0.7298	NPC81175
Intermediate Similarity	0.7296	NPC199667
Intermediate Similarity	0.7294	NPC53534
Intermediate Similarity	0.7289	NPC276517
Intermediate Similarity	0.7287	NPC470785
Intermediate Similarity	0.7287	NPC470784
Intermediate Similarity	0.728	NPC60621
Intermediate Similarity	0.7277	NPC471080
Intermediate Similarity	0.7277	NPC39500
Intermediate Similarity	0.7277	NPC469592
Intermediate Similarity	0.7276	NPC89549
Intermediate Similarity	0.7273	NPC472111
Intermediate Similarity	0.7269	NPC473312
Intermediate Similarity	0.7265	NPC87413
Intermediate Similarity	0.7261	NPC476098
Intermediate Similarity	0.7259	NPC152620
Intermediate Similarity	0.7255	NPC303374
Intermediate Similarity	0.7254	NPC474688
Intermediate Similarity	0.7253	NPC473181
Intermediate Similarity	0.725	NPC162748
Intermediate Similarity	0.7243	NPC471762
Intermediate Similarity	0.7243	NPC274640
Intermediate Similarity	0.7238	NPC174760
Intermediate Similarity	0.7237	NPC241024
Intermediate Similarity	0.7234	NPC264176
Intermediate Similarity	0.7231	NPC202503
Intermediate Similarity	0.7229	NPC285558
Intermediate Similarity	0.7227	NPC469594
Intermediate Similarity	0.7224	NPC469554
Intermediate Similarity	0.7224	NPC101543
Intermediate Similarity	0.722	NPC111602
Intermediate Similarity	0.722	NPC322482
Intermediate Similarity	0.722	NPC102338
Intermediate Similarity	0.722	NPC63199
Intermediate Similarity	0.722	NPC196251
Intermediate Similarity	0.7218	NPC101350
Intermediate Similarity	0.7218	NPC131486
Intermediate Similarity	0.7216	NPC244543
Intermediate Similarity	0.7215	NPC74969
Intermediate Similarity	0.7205	NPC214428
Intermediate Similarity	0.7205	NPC176538
Intermediate Similarity	0.7198	NPC277350
Intermediate Similarity	0.7197	NPC473179
Intermediate Similarity	0.7193	NPC52557
Intermediate Similarity	0.7191	NPC9894
Intermediate Similarity	0.7179	NPC469743
Intermediate Similarity	0.7177	NPC6786
Intermediate Similarity	0.7177	NPC235685
Intermediate Similarity	0.7175	NPC21425
Intermediate Similarity	0.7174	NPC267423
Intermediate Similarity	0.7172	NPC194740
Intermediate Similarity	0.7167	NPC321428
Intermediate Similarity	0.7167	NPC249583
Intermediate Similarity	0.7161	NPC48353
Intermediate Similarity	0.7161	NPC308137
Intermediate Similarity	0.7161	NPC310211
Intermediate Similarity	0.7156	NPC92111
Intermediate Similarity	0.7155	NPC184408
Intermediate Similarity	0.7149	NPC475422
Intermediate Similarity	0.7149	NPC167860
Intermediate Similarity	0.7149	NPC123976
Intermediate Similarity	0.7137	NPC198503
Intermediate Similarity	0.7131	NPC257851
Intermediate Similarity	0.713	NPC312870
Intermediate Similarity	0.713	NPC138830
Intermediate Similarity	0.713	NPC199851
Intermediate Similarity	0.713	NPC294909
Intermediate Similarity	0.713	NPC128265
Intermediate Similarity	0.713	NPC254240
Intermediate Similarity	0.7118	NPC72211
Intermediate Similarity	0.7111	NPC106833
Intermediate Similarity	0.7111	NPC76748
Intermediate Similarity	0.7111	NPC469497
Intermediate Similarity	0.7108	NPC473183
Intermediate Similarity	0.7102	NPC66777
Intermediate Similarity	0.7095	NPC150239
Intermediate Similarity	0.7095	NPC225279
Intermediate Similarity	0.7095	NPC323969
Intermediate Similarity	0.7094	NPC53344
Intermediate Similarity	0.7093	NPC203972
Intermediate Similarity	0.7093	NPC307963
Intermediate Similarity	0.7092	NPC475844
Intermediate Similarity	0.709	NPC319232
Intermediate Similarity	0.709	NPC24370
Intermediate Similarity	0.7082	NPC475847
Intermediate Similarity	0.7082	NPC185742
Intermediate Similarity	0.7074	NPC70956
Intermediate Similarity	0.7074	NPC243834
Intermediate Similarity	0.7073	NPC223242
Intermediate Similarity	0.7068	NPC477549
Intermediate Similarity	0.7067	NPC128751
Intermediate Similarity	0.7067	NPC296527
Intermediate Similarity	0.7064	NPC39679
Intermediate Similarity	0.7064	NPC87755
Intermediate Similarity	0.7063	NPC45048
Intermediate Similarity	0.7061	NPC34580
Intermediate Similarity	0.7061	NPC124920
Intermediate Similarity	0.7061	NPC261251

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
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