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

Show entries

Search:

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

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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