NPASS drugs

Drug Information

Drug ID:	NPD8467
Drug Name:	Vinblastine
Molecular Formula:	C46H58N4O9
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(=O)OC)OC(=O)C)(CC)C=CC1
Standard InCHI:	"InChI=1S/C46H58N4O9/c1-8-42(54)23-28-24-45(40(52)57-6,36-30(15-19-49(25-28)26-42)29-13-10-11-14-33(29)47-36)32-21-31-34(22-35(32)56-5)48(4)38-44(31)17-20-50-18-12-16-43(9-2,37(44)50)39(59-27(3)51)46(38,55)41(53)58-7/h10-14,16,21-22,28,37-39,47,54-55H,8-9,15,17-20,23-26H2,1-7H3/t28-,37+,38-,39-,42+,43-,44-,45+,46+/m1/s1"
Standard InCHIKey:	JXLYSJRDGCGARV-XQKSVPLYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	DrugBank

Structural Similarity Between NPASS Natural Products and NPD8467

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	97260
0.1-0.2	112322
0.2-0.3	1984
0.3-0.4	125
0.4-0.5	4
0.5-0.6	6
0.6-0.7	9
0.7-0.8	6
0.8-0.85	10
0.85-0.9	2
0.9-0.95	0
0.95-1	12

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	NPC195788
High Similarity	1.0	NPC104381
High Similarity	1.0	NPC324460
High Similarity	1.0	NPC237901
High Similarity	1.0	NPC495838
High Similarity	1.0	NPC496093
High Similarity	1.0	NPC538376
High Similarity	1.0	NPC586833
High Similarity	1.0	NPC599800
High Similarity	1.0	NPC605092
High Similarity	0.9667	NPC485509
High Similarity	0.9667	NPC612083
High Similarity	0.877	NPC108849
High Similarity	0.877	NPC584860
Intermediate Similarity	0.8492	NPC157671
Intermediate Similarity	0.84	NPC316127
Intermediate Similarity	0.84	NPC597396
Intermediate Similarity	0.8268	NPC509295
Intermediate Similarity	0.8268	NPC608514
Intermediate Similarity	0.8189	NPC277353
Intermediate Similarity	0.8189	NPC526605
Intermediate Similarity	0.8189	NPC535914
Intermediate Similarity	0.8189	NPC600057
Intermediate Similarity	0.8189	NPC600181
Intermediate Similarity	0.7313	NPC481035
Intermediate Similarity	0.7111	NPC25232
Intermediate Similarity	0.7111	NPC492313
Intermediate Similarity	0.7101	NPC260909
Intermediate Similarity	0.7101	NPC94234
Intermediate Similarity	0.7101	NPC599819
Remote Similarity	0.6985	NPC302688
Remote Similarity	0.6985	NPC599845
Remote Similarity	0.6957	NPC270946
Remote Similarity	0.6912	NPC475430
Remote Similarity	0.6912	NPC567664
Remote Similarity	0.6901	NPC489610
Remote Similarity	0.6861	NPC129871
Remote Similarity	0.6338	NPC29896
Remote Similarity	0.625	NPC328521
Remote Similarity	0.5918	NPC481036
Remote Similarity	0.529	NPC475620
Remote Similarity	0.529	NPC501114
Remote Similarity	0.5154	NPC515686
Remote Similarity	0.5068	NPC86782
Remote Similarity	0.5033	NPC142656

Drug Structure

NPD8467 OpenBabel08211713022D 62 70 0 0 1 0 0 0 0 0999 V2000 -2.5033 1.7783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6799 -2.8155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2840 -1.2285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9731 0.3276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7149 2.8290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8790 3.3236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7930 0.0210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9705 0.8942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8074 -3.3042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4015 3.6442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6150 4.2618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7890 -4.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2598 2.6542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6869 3.8895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7288 0.6721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7401 -3.7711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2538 -0.8148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0459 -3.4110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8655 -0.3185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3340 -1.6238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0161 -0.2327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1222 0.9594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6719 -0.2870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9881 -0.2108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3817 -1.4718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1780 -0.3434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3289 -2.2275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4554 -1.0949 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3317 2.2820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9873 1.3431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8089 -0.4137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2236 0.5443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5452 2.8996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3619 0.1824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3295 1.1404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9880 1.3805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2048 -2.1238 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0026 -0.9667 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5986 -2.3052 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7579 1.5957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2107 -0.6835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4385 0.0474 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9480 -2.7930 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2048 -1.1238 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1985 0.7668 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6229 -1.4925 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7148 2.3425 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.0997 -0.1594 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3335 -1.1652 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 0.2538 -2.4329 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 5.2165 -2.6882 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7554 1.5258 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8040 0.2301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9712 0.9316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9559 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0347 2.0959 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3197 2.4946 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2052 -0.7880 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4862 -2.7659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7760 2.6868 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5033 1.7783 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 27 1 0 0 0 0 4 48 1 0 0 0 0 5 56 1 0 0 0 0 6 57 1 0 0 0 0 7 58 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 16 2 0 0 0 0 12 18 1 0 0 0 0 13 29 2 0 0 0 0 14 33 2 0 0 0 0 15 19 1 0 0 0 0 15 30 1 0 0 0 0 16 43 1 0 0 0 0 17 20 1 0 0 0 0 18 50 1 0 0 0 0 19 49 1 0 0 0 0 20 50 1 0 0 0 0 21 31 2 0 0 0 0 21 32 1 0 0 0 0 22 34 2 0 0 0 0 22 35 1 0 0 0 0 23 42 1 0 0 0 0 24 28 1 0 0 0 0 24 45 1 0 0 0 0 25 28 1 0 0 0 0 25 49 1 0 0 0 0 26 42 1 0 0 0 0 26 49 1 0 0 0 0 27 51 2 0 0 0 0 27 59 1 0 0 0 0 28 23 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 44 1 0 0 0 0 32 35 2 0 0 0 0 32 45 1 0 0 0 0 33 47 1 0 0 0 0 34 48 1 0 0 0 0 35 56 1 0 0 0 0 36 45 1 0 0 0 0 36 47 1 0 0 0 0 37 43 1 6 0 0 0 37 44 1 0 0 0 0 37 50 1 0 0 0 0 38 44 1 1 0 0 0 38 46 1 0 0 0 0 38 48 1 0 0 0 0 39 43 1 6 0 0 0 39 46 1 0 0 0 0 39 59 1 0 0 0 0 40 52 2 0 0 0 0 40 57 1 0 0 0 0 41 46 1 0 0 0 0 41 53 2 0 0 0 0 41 58 1 0 0 0 0 42 8 1 6 0 0 0 42 54 1 0 0 0 0 43 9 1 1 0 0 0 44 17 1 6 0 0 0 45 40 1 6 0 0 0 46 55 1 6 0 0 0 47 60 1 0 0 0 0 54 61 1 0 0 0 0 55 62 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000785
DrugBank	DB00570
ChEMBL	CHEMBL159
IUPHAR/BPS
PharmaGKB	PA451877
KEGG Drug
PubChem CID	0
ChEBI
CAS Number	865-21-4

Drug Properties

Molecular Weight	810.42
ALogP	-1.9554
MLogP	5.09
XLogP	4.011
HDA	12
HBD	3
Rotatable Bonds	19
TPSA	154.1
RO5 Violation	1