NPASS drugs

Drug Information

Drug ID:	NPD8428
Drug Name:	Vinorelbine
Molecular Formula:	C45H54N4O8
Canonical SMILES:	CCC1=C[C@@H]2CN(C1)Cc1c3ccccc3[nH]c1[C@@](C2)(C(=O)OC)c1cc2c(cc1OC)N([C@@H]1[C@@]32CCN2[C@H]3[C@@](CC)(C=CC2)[C@H]([C@@]1(O)C(=O)OC)OC(=O)C)C
Standard InCHI:	"InChI=1S/C45H54N4O8/c1-8-27-19-28-22-44(40(51)55-6,36-30(25-48(23-27)24-28)29-13-10-11-14-33(29)46-36)32-20-31-34(21-35(32)54-5)47(4)38-43(31)16-18-49-17-12-15-42(9-2,37(43)49)39(57-26(3)50)45(38,53)41(52)56-7/h10-15,19-21,28,37-39,46,53H,8-9,16-18,22-25H2,1-7H3/t28-,37-,38+,39+,42+,43+,44-,45+/m0/s1"
Standard InCHIKey:	GBABOYUKABKIAF-GHYRFKGUSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	DrugBank

Structural Similarity Between NPASS Natural Products and NPD8428

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	92203
0.1-0.2	117506
0.2-0.3	1952
0.3-0.4	30
0.4-0.5	9
0.5-0.6	9
0.6-0.7	22
0.7-0.8	2
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	2

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	NPC302688
High Similarity	1.0	NPC599845
Intermediate Similarity	0.8189	NPC509295
Intermediate Similarity	0.8189	NPC608514
Intermediate Similarity	0.7143	NPC108849
Intermediate Similarity	0.7143	NPC584860
Remote Similarity	0.6985	NPC195788
Remote Similarity	0.6985	NPC104381
Remote Similarity	0.6985	NPC324460
Remote Similarity	0.6985	NPC237901
Remote Similarity	0.6985	NPC495838
Remote Similarity	0.6985	NPC496093
Remote Similarity	0.6985	NPC538376
Remote Similarity	0.6985	NPC586833
Remote Similarity	0.6985	NPC599800
Remote Similarity	0.6985	NPC605092
Remote Similarity	0.6934	NPC157671
Remote Similarity	0.6912	NPC25232
Remote Similarity	0.6912	NPC277353
Remote Similarity	0.6912	NPC492313
Remote Similarity	0.6912	NPC526605
Remote Similarity	0.6912	NPC535914
Remote Similarity	0.6912	NPC600057
Remote Similarity	0.6912	NPC600181
Remote Similarity	0.6786	NPC485509
Remote Similarity	0.6786	NPC612083
Remote Similarity	0.6294	NPC270946
Remote Similarity	0.6268	NPC481035
Remote Similarity	0.5862	NPC129871
Remote Similarity	0.5793	NPC316127
Remote Similarity	0.5793	NPC597396
Remote Similarity	0.5578	NPC475430
Remote Similarity	0.5578	NPC567664
Remote Similarity	0.5329	NPC481036
Remote Similarity	0.5325	NPC475620
Remote Similarity	0.5325	NPC501114
Remote Similarity	0.5077	NPC515686

Drug Structure

NPD8428 OpenBabel08211713022D 59 67 0 0 1 0 0 0 0 0999 V2000 -1.0206 1.2651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0803 -2.0804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6844 -0.4934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3735 1.0627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1153 3.5641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1813 4.1198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1934 0.7562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7008 0.5321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2078 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0588 -2.7430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1113 -2.4234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1894 -3.3450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8094 -2.0823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0857 -1.4429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1404 -3.0360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3458 -0.0797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5538 -2.6759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9336 -0.8887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8587 1.5563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5835 0.5024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5226 1.6945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6137 2.0806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1884 0.1117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1782 1.0975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1952 -0.4670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7293 -1.4924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6757 0.7546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5996 1.9131 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6125 -1.1019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2093 -0.2995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2092 0.3215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8232 1.2794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6649 -0.7822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7623 0.9175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2701 1.8755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6306 0.5161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6052 -1.3887 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4030 -0.2316 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9990 -1.5701 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2588 2.3895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6111 0.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3484 -2.0579 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6052 -0.3887 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7981 1.5019 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0233 -0.7574 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6762 0.2177 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5001 0.5757 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.0107 0.1117 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.3458 -1.6977 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 4.6169 -1.9531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2578 2.4343 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2043 0.9652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9531 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5649 2.8311 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7205 3.2323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6056 -0.0529 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8866 -2.0308 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1262 0.8146 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 9 1 0 0 0 0 3 26 1 0 0 0 0 4 47 1 0 0 0 0 5 54 1 0 0 0 0 6 55 1 0 0 0 0 7 56 1 0 0 0 0 8 27 1 0 0 0 0 10 11 2 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 13 29 2 0 0 0 0 14 33 2 0 0 0 0 15 42 1 0 0 0 0 16 18 1 0 0 0 0 17 49 1 0 0 0 0 18 49 1 0 0 0 0 19 27 2 0 0 0 0 20 31 2 0 0 0 0 20 32 1 0 0 0 0 21 34 2 0 0 0 0 21 35 1 0 0 0 0 22 28 1 0 0 0 0 22 44 1 0 0 0 0 23 27 1 0 0 0 0 23 48 1 0 0 0 0 24 28 1 0 0 0 0 24 48 1 0 0 0 0 25 30 1 0 0 0 0 25 48 1 0 0 0 0 26 50 2 0 0 0 0 26 57 1 0 0 0 0 28 19 1 1 0 0 0 29 30 1 0 0 0 0 29 33 1 0 0 0 0 30 36 2 0 0 0 0 31 34 1 0 0 0 0 31 43 1 0 0 0 0 32 35 2 0 0 0 0 32 44 1 0 0 0 0 33 46 1 0 0 0 0 34 47 1 0 0 0 0 35 54 1 0 0 0 0 36 44 1 0 0 0 0 36 46 1 0 0 0 0 37 42 1 6 0 0 0 37 43 1 0 0 0 0 37 49 1 0 0 0 0 38 43 1 1 0 0 0 38 45 1 0 0 0 0 38 47 1 0 0 0 0 39 42 1 6 0 0 0 39 45 1 0 0 0 0 39 57 1 0 0 0 0 40 51 2 0 0 0 0 40 55 1 0 0 0 0 41 52 2 0 0 0 0 41 56 1 0 0 0 0 42 9 1 1 0 0 0 43 16 1 6 0 0 0 44 40 1 1 0 0 0 45 41 1 1 0 0 0 45 53 1 0 0 0 0 46 58 1 0 0 0 0 53 59 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000765
DrugBank	DB00361
ChEMBL	CHEMBL607994
IUPHAR/BPS
PharmaGKB	PA451881
KEGG Drug	D08680
PubChem CID	0
ChEBI	480999
CAS Number	71486-22-1

Drug Properties

Molecular Weight	778.39
ALogP	-0.7124
MLogP	5.09
XLogP	3.903
HDA	11
HBD	2
Rotatable Bonds	18
TPSA	133.87
RO5 Violation	1