NPASS drugs

Drug Information

Drug ID:	NPD8269
Drug Name:	Eribulin
Molecular Formula:	C40H59NO11
Canonical SMILES:	NC[C@H](C[C@H]1O[C@@H]2[C@@H]([C@H]1OC)CC(=O)CC1CC[C@H]3[C@H](O1)[C@@H]1O[C@]4(CC[C@@H]5O[C@@H](CC[C@@H]6O[C@H](C2)C(=C)[C@@H](C6)C)C(=C)C5)O[C@@H]2[C@H](O3)[C@H]1O[C@@H]2C4)O
Standard InCHI:	InChI=1S/C40H59NO11/c1-19-11-24-5-7-28-20(2)12-26(45-28)9-10-40-17-33-36(51-40)37-38(50-33)39(52-40)35-29(49-37)8-6-25(47-35)13-22(42)14-27-31(16-30(46-24)21(19)3)48-32(34(27)44-4)15-23(43)18-41/h19,23-39,43H,2-3,5-18,41H2,1,4H3/t19-,23+,24+,25?,26+,27+,28+,29+,30-,31+,32-,33-,34-,35+,36+,37+,38-,39+,40+/m1/s1
Standard InCHIKey:	UFNVPOGXISZXJD-WVMZDRIUSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	DrugBank

Structural Similarity Between NPASS Natural Products and NPD8269

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	80
0.1-0.2	744
0.2-0.3	3411
0.3-0.4	11384
0.4-0.5	9990
0.5-0.6	4826
0.6-0.7	442
0.7-0.8	13
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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

Similarity Level	Similarity Score	Natural Product ID
Intermediate Similarity	0.7851	NPC308858
Intermediate Similarity	0.7851	NPC475537
Intermediate Similarity	0.7686	NPC473849
Intermediate Similarity	0.7686	NPC312498
Intermediate Similarity	0.75	NPC473771
Intermediate Similarity	0.75	NPC475275
Intermediate Similarity	0.7209	NPC475298
Intermediate Similarity	0.7188	NPC313802
Intermediate Similarity	0.7188	NPC477515
Intermediate Similarity	0.7188	NPC67917
Intermediate Similarity	0.7188	NPC314268
Intermediate Similarity	0.7016	NPC313668
Intermediate Similarity	0.7016	NPC315836
Remote Similarity	0.697	NPC315783
Remote Similarity	0.6935	NPC475150
Remote Similarity	0.6746	NPC473578
Remote Similarity	0.6742	NPC317635
Remote Similarity	0.6742	NPC329008
Remote Similarity	0.6721	NPC67296
Remote Similarity	0.6719	NPC469865
Remote Similarity	0.6716	NPC186339
Remote Similarity	0.6696	NPC314364
Remote Similarity	0.6696	NPC51662
Remote Similarity	0.6691	NPC314361
Remote Similarity	0.6667	NPC313569
Remote Similarity	0.664	NPC476740
Remote Similarity	0.664	NPC476738
Remote Similarity	0.6613	NPC473816
Remote Similarity	0.6613	NPC474581
Remote Similarity	0.6613	NPC475367
Remote Similarity	0.6613	NPC309398
Remote Similarity	0.6612	NPC304445
Remote Similarity	0.6612	NPC236580
Remote Similarity	0.6585	NPC305085
Remote Similarity	0.6585	NPC84042
Remote Similarity	0.6581	NPC92974
Remote Similarity	0.6569	NPC314282
Remote Similarity	0.6569	NPC11732
Remote Similarity	0.6535	NPC475960
Remote Similarity	0.6532	NPC80144
Remote Similarity	0.6529	NPC476009
Remote Similarity	0.6529	NPC158416
Remote Similarity	0.6529	NPC76862
Remote Similarity	0.6529	NPC39859
Remote Similarity	0.6529	NPC470883
Remote Similarity	0.6512	NPC126897
Remote Similarity	0.6512	NPC297945
Remote Similarity	0.65	NPC316401
Remote Similarity	0.6496	NPC177629
Remote Similarity	0.6496	NPC58219
Remote Similarity	0.6493	NPC108072
Remote Similarity	0.6493	NPC142882
Remote Similarity	0.648	NPC473148
Remote Similarity	0.6475	NPC316205
Remote Similarity	0.6475	NPC315387
Remote Similarity	0.6471	NPC314629
Remote Similarity	0.6466	NPC475309
Remote Similarity	0.6462	NPC469466
Remote Similarity	0.6454	NPC224623
Remote Similarity	0.6446	NPC475900
Remote Similarity	0.6444	NPC183353
Remote Similarity	0.6444	NPC469812
Remote Similarity	0.6444	NPC170880
Remote Similarity	0.6439	NPC277583
Remote Similarity	0.6429	NPC469351
Remote Similarity	0.6429	NPC231271
Remote Similarity	0.6429	NPC470519
Remote Similarity	0.6423	NPC249171
Remote Similarity	0.6423	NPC314451
Remote Similarity	0.6423	NPC313333
Remote Similarity	0.6423	NPC313342
Remote Similarity	0.6423	NPC314512
Remote Similarity	0.6423	NPC49833
Remote Similarity	0.641	NPC186148
Remote Similarity	0.6406	NPC193765
Remote Similarity	0.6403	NPC172823
Remote Similarity	0.64	NPC227622
Remote Similarity	0.6393	NPC474297
Remote Similarity	0.6387	NPC474323
Remote Similarity	0.6387	NPC206614
Remote Similarity	0.6385	NPC471251
Remote Similarity	0.6378	NPC478038
Remote Similarity	0.6378	NPC236644
Remote Similarity	0.6377	NPC474371
Remote Similarity	0.6376	NPC316249
Remote Similarity	0.6371	NPC206711
Remote Similarity	0.6371	NPC271207
Remote Similarity	0.6371	NPC255175
Remote Similarity	0.6371	NPC225978
Remote Similarity	0.6364	NPC71589
Remote Similarity	0.635	NPC1538
Remote Similarity	0.635	NPC42747
Remote Similarity	0.6341	NPC58267
Remote Similarity	0.6341	NPC266842
Remote Similarity	0.6341	NPC263674
Remote Similarity	0.6341	NPC261372
Remote Similarity	0.6338	NPC475487
Remote Similarity	0.6336	NPC276995
Remote Similarity	0.6336	NPC76660
Remote Similarity	0.6333	NPC470373
Remote Similarity	0.6333	NPC329952
Remote Similarity	0.6333	NPC470379
Remote Similarity	0.6331	NPC475273
Remote Similarity	0.6331	NPC168849
Remote Similarity	0.6325	NPC476015
Remote Similarity	0.6325	NPC474949
Remote Similarity	0.6325	NPC475019
Remote Similarity	0.6325	NPC474762
Remote Similarity	0.632	NPC316250
Remote Similarity	0.6312	NPC201359
Remote Similarity	0.6311	NPC167893
Remote Similarity	0.6308	NPC83005
Remote Similarity	0.6308	NPC477997
Remote Similarity	0.6308	NPC475463
Remote Similarity	0.6304	NPC144625
Remote Similarity	0.6299	NPC469869
Remote Similarity	0.6299	NPC474917
Remote Similarity	0.6296	NPC161738
Remote Similarity	0.6294	NPC120420
Remote Similarity	0.6293	NPC473791
Remote Similarity	0.629	NPC255592
Remote Similarity	0.629	NPC261377
Remote Similarity	0.629	NPC308567
Remote Similarity	0.6286	NPC476091
Remote Similarity	0.6286	NPC476078
Remote Similarity	0.6286	NPC471086
Remote Similarity	0.6279	NPC473807
Remote Similarity	0.6277	NPC192309
Remote Similarity	0.627	NPC106668
Remote Similarity	0.626	NPC91771
Remote Similarity	0.626	NPC189629
Remote Similarity	0.626	NPC195645
Remote Similarity	0.626	NPC180722
Remote Similarity	0.626	NPC165332
Remote Similarity	0.626	NPC142529
Remote Similarity	0.6259	NPC210729
Remote Similarity	0.6259	NPC82931
Remote Similarity	0.6259	NPC217901
Remote Similarity	0.6259	NPC172365
Remote Similarity	0.625	NPC170432
Remote Similarity	0.625	NPC163693
Remote Similarity	0.625	NPC99864
Remote Similarity	0.625	NPC147635
Remote Similarity	0.6241	NPC162495
Remote Similarity	0.6241	NPC13071
Remote Similarity	0.6239	NPC329749
Remote Similarity	0.6232	NPC318445
Remote Similarity	0.6232	NPC316133
Remote Similarity	0.6231	NPC471250
Remote Similarity	0.623	NPC190294
Remote Similarity	0.6222	NPC93688
Remote Similarity	0.6222	NPC109603
Remote Similarity	0.622	NPC27687
Remote Similarity	0.622	NPC475928
Remote Similarity	0.6212	NPC474927
Remote Similarity	0.6212	NPC1111
Remote Similarity	0.6212	NPC261750
Remote Similarity	0.6212	NPC471244
Remote Similarity	0.621	NPC323421
Remote Similarity	0.621	NPC328562
Remote Similarity	0.6204	NPC473228
Remote Similarity	0.6204	NPC182900
Remote Similarity	0.6204	NPC470829
Remote Similarity	0.6204	NPC249553
Remote Similarity	0.6202	NPC469788
Remote Similarity	0.6202	NPC290247
Remote Similarity	0.6202	NPC469787
Remote Similarity	0.6202	NPC176756
Remote Similarity	0.6202	NPC148270
Remote Similarity	0.6202	NPC197813
Remote Similarity	0.6202	NPC80338
Remote Similarity	0.6198	NPC12172
Remote Similarity	0.6198	NPC469627
Remote Similarity	0.6198	NPC208886
Remote Similarity	0.6198	NPC184463
Remote Similarity	0.6197	NPC473838
Remote Similarity	0.6197	NPC475389
Remote Similarity	0.6194	NPC88945
Remote Similarity	0.619	NPC162024
Remote Similarity	0.6187	NPC326386
Remote Similarity	0.6187	NPC469494
Remote Similarity	0.6187	NPC477985
Remote Similarity	0.6187	NPC471087
Remote Similarity	0.6186	NPC162071
Remote Similarity	0.6183	NPC49730
Remote Similarity	0.6183	NPC46407
Remote Similarity	0.6183	NPC98633
Remote Similarity	0.6183	NPC98069
Remote Similarity	0.6183	NPC137104
Remote Similarity	0.6183	NPC124053
Remote Similarity	0.6183	NPC320383
Remote Similarity	0.6183	NPC474786
Remote Similarity	0.6179	NPC36954
Remote Similarity	0.6172	NPC203659
Remote Similarity	0.6172	NPC100487
Remote Similarity	0.6172	NPC472748
Remote Similarity	0.617	NPC173173
Remote Similarity	0.617	NPC188291
Remote Similarity	0.6167	NPC474951
Remote Similarity	0.6167	NPC173926

Drug Structure

NPD8269 OpenBabel08211713002D 55 63 0 0 1 0 0 0 0 0999 V2000 -2.7103 0.6290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0833 -0.0387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1625 1.7532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0456 4.4903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0872 -0.3674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4275 1.7903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7727 -0.8390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1520 1.0577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7173 -1.5389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1804 -1.3572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7749 0.2482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3921 -1.0242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4390 2.6465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5605 2.7210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2720 3.7900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9431 1.7991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1397 -0.2590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5451 4.4193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5285 0.6835 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9241 -0.8430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7151 1.1475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9948 2.7576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0902 3.7372 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2689 0.1695 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9309 2.3953 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.2830 -1.5755 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0974 2.5393 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3469 -1.2132 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3797 0.9301 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1943 1.2909 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5690 2.2249 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8171 3.1078 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1397 0.4992 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2507 3.0850 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1906 1.5495 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4527 0.4992 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4527 1.2577 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8062 1.6370 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0089 1.0126 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7861 -0.6383 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1817 5.1544 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9404 3.5757 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4535 3.0021 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7425 3.7285 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8388 -1.4644 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3054 0.7351 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5051 2.0211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0138 2.5762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0108 0.7842 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1397 1.2577 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4527 -0.2590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6366 5.8365 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3635 5.2072 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2718 2.9493 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2 20 2 0 0 0 0 3 21 2 0 0 0 0 4 44 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 6 25 1 0 0 0 0 9 10 1 0 0 0 0 11 19 1 0 0 0 0 11 24 1 0 0 0 0 12 20 1 0 0 0 0 12 26 1 0 0 0 0 13 22 1 0 0 0 0 13 25 1 0 0 0 0 14 22 1 0 0 0 0 17 40 1 0 0 0 0 18 23 1 0 0 0 0 18 41 1 0 0 0 0 19 1 1 6 0 0 0 19 21 1 0 0 0 0 20 28 1 0 0 0 0 21 30 1 0 0 0 0 22 42 2 0 0 0 0 23 15 1 6 0 0 0 23 43 1 0 0 0 0 24 5 1 6 0 0 0 24 46 1 0 0 0 0 25 47 1 0 0 0 0 26 9 1 6 0 0 0 26 45 1 0 0 0 0 27 14 1 1 0 0 0 27 31 1 0 0 0 0 27 34 1 0 0 0 0 28 7 1 1 0 0 0 28 45 1 0 0 0 0 29 8 1 6 0 0 0 29 35 1 0 0 0 0 29 49 1 0 0 0 0 30 16 1 6 0 0 0 30 46 1 0 0 0 0 31 16 1 6 0 0 0 31 48 1 0 0 0 0 32 15 1 6 0 0 0 32 34 1 0 0 0 0 32 48 1 0 0 0 0 33 17 1 6 0 0 0 33 36 1 0 0 0 0 33 50 1 0 0 0 0 34 44 1 6 0 0 0 35 39 1 0 0 0 0 35 47 1 6 0 0 0 36 37 1 0 0 0 0 36 51 1 6 0 0 0 37 38 1 0 0 0 0 37 49 1 6 0 0 0 38 39 1 0 0 0 0 38 50 1 1 0 0 0 39 52 1 6 0 0 0 40 10 1 6 0 0 0 40 51 1 0 0 0 0 40 52 1 0 0 0 0 41 53 1 0 0 0 0 41 54 1 0 0 0 0 43 55 1 0 0 0 0 M END $$$$

External Identifiers

TTD
DrugBank	DB08871
ChEMBL	CHEMBL1683590
IUPHAR/BPS
PharmaGKB
KEGG Drug	D08914
PubChem CID
ChEBI	63587
CAS Number	253128-41-5

Drug Properties

Molecular Weight	729.41
ALogP	-4.8867
MLogP	4.54
XLogP	0.56
HDA	12
HBD	2
Rotatable Bonds	8
TPSA	146.39
RO5 Violation	1