NPASS drugs

Drug Information

Drug ID:	NPD8364
Drug Name:	Vindesine
Molecular Formula:	C43H55N5O7
Canonical SMILES:	COc1cc2N(C)[C@@H]3[C@@]4(c2cc1[C@]1(C[C@@H]2CN(CCc5c1[nH]c1c5cccc1)C[C@](C2)(O)CC)C(=O)OC)CCN1[C@H]4[C@@]([C@H]([C@]3(O)C(=N)O)O)(CC)C=CC1
Standard InCHI:	"InChI=1S/C43H55N5O7/c1-6-39(52)21-25-22-42(38(51)55-5,33-27(13-17-47(23-25)24-39)26-11-8-9-12-30(26)45-33)29-19-28-31(20-32(29)54-4)46(3)35-41(28)15-18-48-16-10-14-40(7-2,34(41)48)36(49)43(35,53)37(44)50/h8-12,14,19-20,25,34-36,45,49,52-53H,6-7,13,15-18,21-24H2,1-5H3,(H2,44,50)/t25-,34+,35-,36-,39+,40-,41-,42+,43+/m1/s1"
Standard InCHIKey:	HHJUWIANJFBDHT-KOTLKJBCSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD8364

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	88385
0.1-0.2	120656
0.2-0.3	2466
0.3-0.4	187
0.4-0.5	7
0.5-0.6	8
0.6-0.7	13
0.7-0.8	4
0.8-0.85	12
0.85-0.9	0
0.9-0.95	2
0.95-1	0

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	0.9008	NPC316127
High Similarity	0.9008	NPC597396
Intermediate Similarity	0.8125	NPC195788
Intermediate Similarity	0.8125	NPC104381
Intermediate Similarity	0.8125	NPC324460
Intermediate Similarity	0.8125	NPC237901
Intermediate Similarity	0.8125	NPC495838
Intermediate Similarity	0.8125	NPC496093
Intermediate Similarity	0.8125	NPC538376
Intermediate Similarity	0.8125	NPC586833
Intermediate Similarity	0.8125	NPC599800
Intermediate Similarity	0.8125	NPC605092
Intermediate Similarity	0.8015	NPC485509
Intermediate Similarity	0.8015	NPC612083
Intermediate Similarity	0.7132	NPC157671
Intermediate Similarity	0.7111	NPC129871
Intermediate Similarity	0.709	NPC108849
Intermediate Similarity	0.709	NPC584860
Remote Similarity	0.6691	NPC509295
Remote Similarity	0.6691	NPC608514
Remote Similarity	0.6619	NPC277353
Remote Similarity	0.6619	NPC526605
Remote Similarity	0.6619	NPC535914
Remote Similarity	0.6619	NPC600057
Remote Similarity	0.6619	NPC600181
Remote Similarity	0.6276	NPC260909
Remote Similarity	0.6276	NPC94234
Remote Similarity	0.6276	NPC599819
Remote Similarity	0.6224	NPC29896
Remote Similarity	0.6216	NPC489610
Remote Similarity	0.6138	NPC328521
Remote Similarity	0.589	NPC481035
Remote Similarity	0.5714	NPC25232
Remote Similarity	0.5714	NPC492313
Remote Similarity	0.5608	NPC302688
Remote Similarity	0.5608	NPC599845
Remote Similarity	0.56	NPC270946
Remote Similarity	0.5541	NPC475430
Remote Similarity	0.5541	NPC567664

Drug Structure

NPD8364 OpenBabel08211713012D 61 69 0 0 1 0 0 0 0 0999 V2000 -2.4031 1.6970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7800 -2.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0733 0.2464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8151 2.7477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7789 3.2423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8704 0.8129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9076 -3.3855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3013 3.5629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5148 4.1805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8892 -4.1614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1597 2.5730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5867 3.8083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6287 0.5909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8402 -3.8524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3539 -0.8961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1460 -3.4923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7654 -0.3997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2339 -1.7051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1162 -0.3140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2224 0.8782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5717 -0.3683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8880 -0.2921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2815 -1.5531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0778 -0.4246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3553 -1.1762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2316 2.2007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8872 1.2619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9090 -0.4949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1234 0.4631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4451 2.8183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4621 0.1012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4296 1.0591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8879 1.2993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3050 -2.2051 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1028 -1.0479 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6987 -2.3865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3109 -0.7647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6577 1.5145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3384 -0.0338 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0481 -2.8742 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3050 -1.2051 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0984 0.6856 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7231 -1.5737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9041 0.1488 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6147 2.2612 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.1999 -0.2406 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.2333 -1.2464 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 0.3539 -2.5141 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 3.5863 -2.8471 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3054 -0.8692 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6553 1.4445 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8711 0.8503 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9553 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1349 2.0147 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2195 2.4134 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4919 0.9579 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6758 2.6056 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4290 -2.3088 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8932 -0.0602 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4031 1.6970 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 6 1 0 0 0 0 2 7 1 0 0 0 0 3 46 1 0 0 0 0 4 54 1 0 0 0 0 5 55 1 0 0 0 0 8 9 2 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 26 2 0 0 0 0 12 30 2 0 0 0 0 13 17 1 0 0 0 0 13 27 1 0 0 0 0 14 40 1 0 0 0 0 15 18 1 0 0 0 0 16 48 1 0 0 0 0 17 47 1 0 0 0 0 18 48 1 0 0 0 0 19 28 2 0 0 0 0 19 29 1 0 0 0 0 20 31 2 0 0 0 0 20 32 1 0 0 0 0 21 39 1 0 0 0 0 22 25 1 0 0 0 0 22 42 1 0 0 0 0 23 25 1 0 0 0 0 23 47 1 0 0 0 0 24 39 1 0 0 0 0 24 47 1 0 0 0 0 25 21 1 1 0 0 0 26 27 1 0 0 0 0 26 30 1 0 0 0 0 27 33 2 0 0 0 0 28 31 1 0 0 0 0 28 41 1 0 0 0 0 29 32 2 0 0 0 0 29 42 1 0 0 0 0 30 45 1 0 0 0 0 31 46 1 0 0 0 0 32 54 1 0 0 0 0 33 42 1 0 0 0 0 33 45 1 0 0 0 0 34 40 1 6 0 0 0 34 41 1 0 0 0 0 34 48 1 0 0 0 0 35 41 1 1 0 0 0 35 43 1 0 0 0 0 35 46 1 0 0 0 0 36 40 1 6 0 0 0 36 43 1 0 0 0 0 36 49 1 0 0 0 0 37 43 1 0 0 0 0 37 44 2 0 0 0 0 37 50 1 0 0 0 0 38 51 2 0 0 0 0 38 55 1 0 0 0 0 39 6 1 6 0 0 0 39 52 1 0 0 0 0 40 7 1 1 0 0 0 41 15 1 6 0 0 0 42 38 1 6 0 0 0 43 53 1 6 0 0 0 44 56 1 0 0 0 0 45 57 1 0 0 0 0 49 58 1 0 0 0 0 50 59 1 0 0 0 0 52 60 1 0 0 0 0 53 61 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000949
DrugBank	DB00309
ChEMBL	CHEMBL219146
IUPHAR/BPS
PharmaGKB	PA10232
KEGG Drug	D01769
PubChem CID	40839
ChEBI	36373
CAS Number	53643-48-4

Drug Properties

Molecular Weight	753.41
ALogP	-2.4273
MLogP	4.87
XLogP	4.214
HDA	11
HBD	6
Rotatable Bonds	16
TPSA	165.81
RO5 Violation	2