NPASS drugs

Drug Information

Drug ID:	NPD8462
Drug Name:	simotaxel
Molecular Formula:	C46H57NO15S
Canonical SMILES:	CC(OC(=N[C@H]([C@H](C(=O)O[C@H]1C[C@@]2(O)[C@@H](OC(=O)c3ccccc3)[C@@H]3[C@@]4(CO[C@@H]4C[C@@H]([C@]3(C(=O)[C@@H](C(=C1C)C2(C)C)OC(=O)C1CCCC1)C)O)OC(=O)C)O)c1cccs1)O)C
Standard InCHI:	"InChI=1S/C46H57NO15S/c1-23(2)58-42(55)47-33(29-18-13-19-63-29)34(50)41(54)59-28-21-46(56)38(61-40(53)27-14-9-8-10-15-27)36-44(7,30(49)20-31-45(36,22-57-31)62-25(4)48)37(51)35(32(24(28)3)43(46,5)6)60-39(52)26-16-11-12-17-26/h8-10,13-15,18-19,23,26,28,30-31,33-36,38,49-50,56H,11-12,16-17,20-22H2,1-7H3,(H,47,55)/t28-,30-,31+,33-,34+,35+,36-,38-,44+,45-,46+/m0/s1"
Standard InCHIKey:	SLGIWUWTSWJBQE-VLCCYYTCSA-N
Max Developmental Stage:	Phase 2
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD8462

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	50948
0.1-0.2	154730
0.2-0.3	5767
0.3-0.4	154
0.4-0.5	56
0.5-0.6	48
0.6-0.7	33
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
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
Intermediate Similarity	0.7018	NPC471623
Remote Similarity	0.6581	NPC208553
Remote Similarity	0.6581	NPC181964
Remote Similarity	0.6581	NPC184289
Remote Similarity	0.6581	NPC307628
Remote Similarity	0.6529	NPC487361
Remote Similarity	0.6529	NPC22933
Remote Similarity	0.6525	NPC33372
Remote Similarity	0.6525	NPC52912
Remote Similarity	0.6525	NPC67246
Remote Similarity	0.6525	NPC324251
Remote Similarity	0.6525	NPC206211
Remote Similarity	0.6471	NPC487360
Remote Similarity	0.6471	NPC479182
Remote Similarity	0.6471	NPC479180
Remote Similarity	0.6471	NPC215025
Remote Similarity	0.6471	NPC471629
Remote Similarity	0.6471	NPC306001
Remote Similarity	0.6364	NPC275170
Remote Similarity	0.6311	NPC486061
Remote Similarity	0.6311	NPC486060
Remote Similarity	0.6228	NPC204918
Remote Similarity	0.614	NPC34333
Remote Similarity	0.614	NPC579874
Remote Similarity	0.614	NPC603140
Remote Similarity	0.605	NPC537050
Remote Similarity	0.6033	NPC326042
Remote Similarity	0.6033	NPC327158
Remote Similarity	0.6033	NPC533612
Remote Similarity	0.6033	NPC558987
Remote Similarity	0.6033	NPC601797
Remote Similarity	0.6033	NPC603171
Remote Similarity	0.6	NPC36607
Remote Similarity	0.6	NPC594728
Remote Similarity	0.5984	NPC317994
Remote Similarity	0.5984	NPC328571
Remote Similarity	0.5984	NPC514212
Remote Similarity	0.5984	NPC588327
Remote Similarity	0.595	NPC102167
Remote Similarity	0.595	NPC488127
Remote Similarity	0.5902	NPC317140
Remote Similarity	0.5868	NPC295149
Remote Similarity	0.584	NPC471606
Remote Similarity	0.5645	NPC519154
Remote Similarity	0.5565	NPC200927
Remote Similarity	0.5565	NPC14752
Remote Similarity	0.5565	NPC321072
Remote Similarity	0.5565	NPC215892
Remote Similarity	0.5565	NPC242662
Remote Similarity	0.5556	NPC514511
Remote Similarity	0.552	NPC49524
Remote Similarity	0.552	NPC453583
Remote Similarity	0.552	NPC453588
Remote Similarity	0.552	NPC179899
Remote Similarity	0.552	NPC166498
Remote Similarity	0.552	NPC191193
Remote Similarity	0.5487	NPC155329
Remote Similarity	0.5487	NPC114357
Remote Similarity	0.5487	NPC25820
Remote Similarity	0.5476	NPC471754
Remote Similarity	0.5476	NPC479183
Remote Similarity	0.5476	NPC298358
Remote Similarity	0.5476	NPC479181
Remote Similarity	0.544	NPC327699
Remote Similarity	0.5433	NPC3125
Remote Similarity	0.5433	NPC478329
Remote Similarity	0.5351	NPC582276
Remote Similarity	0.5299	NPC275802
Remote Similarity	0.5299	NPC211426
Remote Similarity	0.5145	NPC241312
Remote Similarity	0.5145	NPC479184
Remote Similarity	0.513	NPC94567
Remote Similarity	0.513	NPC593428
Remote Similarity	0.513	NPC605573
Remote Similarity	0.5118	NPC473300
Remote Similarity	0.5111	NPC116862
Remote Similarity	0.5039	NPC317882
Remote Similarity	0.5039	NPC328084
Remote Similarity	0.5039	NPC327675
Remote Similarity	0.5039	NPC512088
Remote Similarity	0.5036	NPC472391
Remote Similarity	0.5036	NPC27650

Drug Structure

NPD8462 OpenBabel08211713022D 67 73 0 0 1 0 0 0 0 0999 V2000 -6.4129 5.6279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3742 4.3751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0514 -0.5467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9340 -1.9340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4451 -3.0854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5412 -3.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2302 -0.8423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1227 -3.0118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7738 -2.1695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5677 -3.7352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0676 -3.5939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9099 -3.9428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5640 -0.0558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8699 -2.0505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6638 -3.6162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1392 -2.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5021 -3.2495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6551 0.0157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9129 0.7865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7896 1.3676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0795 -1.3796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9117 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5319 4.7240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4189 -1.2033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0534 -2.1700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0257 -2.4722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3149 -2.7738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7067 -0.9689 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4423 0.9022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5791 0.9117 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.9117 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6797 -1.9062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6000 1.2511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8766 0.6961 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9156 -1.0255 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7896 -0.4559 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4598 -0.2360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5536 -1.3365 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3746 -1.6298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4110 -2.6548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0343 1.0450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2043 2.7101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8901 -2.3620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5791 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0095 -2.1261 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4809 2.1550 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5815 -3.9313 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3687 1.3676 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9956 -0.2078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0148 0.4873 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2785 -1.5108 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8559 -3.3781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9153 1.9489 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0466 2.3612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6852 -2.9782 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9117 0.9117 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0853 3.6140 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5877 -0.0650 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8196 -0.9065 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0621 -1.8125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2360 -0.8806 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2196 1.3786 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -2.3687 2.2793 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8380 -0.5567 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7699 2.9162 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2609 -3.6851 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 43 1 0 0 0 0 6 43 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 11 12 1 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 13 18 1 0 0 0 0 13 19 2 0 0 0 0 14 27 2 0 0 0 0 15 27 1 0 0 0 0 16 26 1 0 0 0 0 17 26 1 0 0 0 0 18 29 2 0 0 0 0 19 63 1 0 0 0 0 20 30 1 0 0 0 0 20 31 1 0 0 0 0 21 28 1 0 0 0 0 21 46 1 0 0 0 0 22 45 1 0 0 0 0 22 57 1 0 0 0 0 23 58 1 0 0 0 0 24 28 1 0 0 0 0 24 32 2 0 0 0 0 25 48 2 0 0 0 0 25 62 1 0 0 0 0 26 39 1 0 0 0 0 27 40 1 0 0 0 0 28 59 1 1 0 0 0 29 33 1 0 0 0 0 29 63 1 0 0 0 0 30 44 1 1 0 0 0 30 49 1 0 0 0 0 31 45 1 1 0 0 0 31 57 1 0 0 0 0 32 35 1 0 0 0 0 32 43 1 0 0 0 0 33 34 1 0 0 0 0 33 47 1 6 0 0 0 34 41 1 6 0 0 0 34 50 1 0 0 0 0 35 37 1 0 0 0 0 35 60 1 1 0 0 0 36 38 1 0 0 0 0 36 44 1 1 0 0 0 36 45 1 0 0 0 0 37 44 1 0 0 0 0 37 51 2 0 0 0 0 38 46 1 6 0 0 0 38 61 1 0 0 0 0 39 52 2 0 0 0 0 39 60 1 0 0 0 0 40 53 2 0 0 0 0 40 61 1 0 0 0 0 41 54 2 0 0 0 0 41 59 1 0 0 0 0 42 47 2 3 0 0 0 42 55 1 0 0 0 0 42 58 1 0 0 0 0 43 46 1 0 0 0 0 44 7 1 1 0 0 0 45 62 1 6 0 0 0 46 56 1 6 0 0 0 49 64 1 0 0 0 0 50 65 1 0 0 0 0 55 66 1 0 0 0 0 56 67 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB005909
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	0
ChEBI
CAS Number

Drug Properties

Molecular Weight	895.34
ALogP	-0.649
MLogP	4.65
XLogP	4.978
HDA	16
HBD	4
Rotatable Bonds	27
TPSA	262.25
RO5 Violation	2