NPASS drugs

Drug Information

Drug ID:	NPD7228
Drug Name:	Etoposide
Molecular Formula:	C29H32O13
Canonical SMILES:	COc1cc(cc(c1O)OC)[C@H]1[C@H]2C(=O)OC[C@@H]2[C@@H](c2c1cc1OCOc1c2)O[C@@H]1O[C@@H]2CO[C@H](O[C@H]2[C@@H]([C@H]1O)O)C
Standard InCHI:	InChI=1S/C29H32O13/c1-11-36-9-20-27(40-11)24(31)25(32)29(41-20)42-26-14-7-17-16(38-10-39-17)6-13(14)21(22-15(26)8-37-28(22)33)12-4-18(34-2)23(30)19(5-12)35-3/h4-7,11,15,20-22,24-27,29-32H,8-10H2,1-3H3/t11-,15+,20-,21-,22+,24-,25-,26-,27-,29+/m1/s1
Standard InCHIKey:	VJJPUSNTGOMMGY-MRVIYFEKSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD7228

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	275
0.1-0.2	1083
0.2-0.3	2244
0.3-0.4	4193
0.4-0.5	6779
0.5-0.6	5162
0.6-0.7	4713
0.7-0.8	5273
0.8-0.85	985
0.85-0.9	153
0.9-0.95	19
0.95-1	11

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
High Similarity	1.0	NPC185498
High Similarity	0.9874	NPC179240
High Similarity	0.9809	NPC14294
High Similarity	0.9809	NPC116759
High Similarity	0.9686	NPC306475
High Similarity	0.9682	NPC152424
High Similarity	0.9682	NPC100465
High Similarity	0.9618	NPC91634
High Similarity	0.9618	NPC150943
High Similarity	0.9618	NPC268718
High Similarity	0.95	NPC222531
High Similarity	0.9434	NPC115624
High Similarity	0.9427	NPC237946
High Similarity	0.9427	NPC32373
High Similarity	0.9367	NPC19947
High Similarity	0.9367	NPC181168
High Similarity	0.9367	NPC115281
High Similarity	0.9367	NPC207584
High Similarity	0.9367	NPC163527
High Similarity	0.9299	NPC30009
High Similarity	0.9299	NPC103197
High Similarity	0.925	NPC119910
High Similarity	0.9236	NPC65591
High Similarity	0.9236	NPC178574
High Similarity	0.9236	NPC245948
High Similarity	0.9193	NPC288149
High Similarity	0.913	NPC96593
High Similarity	0.9108	NPC13985
High Similarity	0.9108	NPC210642
High Similarity	0.9057	NPC136757
High Similarity	0.8981	NPC293757
High Similarity	0.8981	NPC174512
High Similarity	0.8981	NPC668
High Similarity	0.8981	NPC477695
High Similarity	0.8981	NPC474965
High Similarity	0.8938	NPC273578
High Similarity	0.8931	NPC477699
High Similarity	0.8924	NPC469707
High Similarity	0.8924	NPC182368
High Similarity	0.8924	NPC9933
High Similarity	0.8924	NPC149505
High Similarity	0.8924	NPC24425
High Similarity	0.8924	NPC469706
High Similarity	0.8924	NPC145979
High Similarity	0.8924	NPC185955
High Similarity	0.8924	NPC225815
High Similarity	0.8924	NPC260781
High Similarity	0.8924	NPC214326
High Similarity	0.8924	NPC218041
High Similarity	0.8882	NPC238834
High Similarity	0.8875	NPC61604
High Similarity	0.8875	NPC299706
High Similarity	0.8875	NPC245615
High Similarity	0.8875	NPC115466
High Similarity	0.8868	NPC477700
High Similarity	0.8862	NPC117911
High Similarity	0.8861	NPC145569
High Similarity	0.8861	NPC216223
High Similarity	0.8854	NPC104024
High Similarity	0.8854	NPC101755
High Similarity	0.8854	NPC65574
High Similarity	0.8854	NPC304687
High Similarity	0.8854	NPC80230
High Similarity	0.8848	NPC25889
High Similarity	0.8827	NPC478055
High Similarity	0.8824	NPC469397
High Similarity	0.8812	NPC56184
High Similarity	0.879	NPC212890
High Similarity	0.8779	NPC188217
High Similarity	0.8765	NPC38699
High Similarity	0.8758	NPC474606
High Similarity	0.8757	NPC476358
High Similarity	0.875	NPC32079
High Similarity	0.8743	NPC474042
High Similarity	0.8743	NPC174734
High Similarity	0.8742	NPC125570
High Similarity	0.8742	NPC477698
High Similarity	0.8742	NPC262455
High Similarity	0.8742	NPC177476
High Similarity	0.8726	NPC477702
High Similarity	0.8722	NPC473803
High Similarity	0.8721	NPC161609
High Similarity	0.8721	NPC275690
High Similarity	0.8712	NPC163635
High Similarity	0.8696	NPC471154
High Similarity	0.8688	NPC158635
High Similarity	0.8688	NPC229882
High Similarity	0.8679	NPC130449
High Similarity	0.8679	NPC248132
High Similarity	0.8671	NPC208797
High Similarity	0.8671	NPC53680
High Similarity	0.8663	NPC80360
High Similarity	0.8663	NPC260300
High Similarity	0.8662	NPC473046
High Similarity	0.8662	NPC472712
High Similarity	0.8662	NPC472713
High Similarity	0.8662	NPC187774
High Similarity	0.8662	NPC118385
High Similarity	0.8655	NPC193377
High Similarity	0.8647	NPC471921
High Similarity	0.8647	NPC114550
High Similarity	0.8647	NPC312006
High Similarity	0.8647	NPC20114
High Similarity	0.8647	NPC474075
High Similarity	0.8647	NPC471922
High Similarity	0.8647	NPC129930
High Similarity	0.8647	NPC471920
High Similarity	0.8647	NPC292712
High Similarity	0.8642	NPC473236
High Similarity	0.8634	NPC164082
High Similarity	0.8634	NPC303519
High Similarity	0.8634	NPC475756
High Similarity	0.8631	NPC59516
High Similarity	0.8625	NPC55158
High Similarity	0.8625	NPC286235
High Similarity	0.8625	NPC51328
High Similarity	0.8614	NPC109061
High Similarity	0.8613	NPC195114
High Similarity	0.8608	NPC286245
High Similarity	0.8608	NPC272619
High Similarity	0.8606	NPC173726
High Similarity	0.8606	NPC241600
High Similarity	0.8605	NPC472723
High Similarity	0.8605	NPC196771
High Similarity	0.8605	NPC297574
High Similarity	0.8599	NPC470811
High Similarity	0.8599	NPC477696
High Similarity	0.8599	NPC477697
High Similarity	0.8598	NPC228357
High Similarity	0.8596	NPC34436
High Similarity	0.8596	NPC219600
High Similarity	0.8596	NPC46640
High Similarity	0.8596	NPC263119
High Similarity	0.8596	NPC166674
High Similarity	0.858	NPC476434
High Similarity	0.858	NPC302610
High Similarity	0.858	NPC21902
High Similarity	0.858	NPC311912
High Similarity	0.8571	NPC167045
High Similarity	0.8571	NPC475738
High Similarity	0.8571	NPC114120
High Similarity	0.8571	NPC472710
High Similarity	0.8571	NPC472709
High Similarity	0.8571	NPC473989
High Similarity	0.8562	NPC304821
High Similarity	0.8555	NPC35266
High Similarity	0.8554	NPC24627
High Similarity	0.8547	NPC469438
High Similarity	0.8547	NPC469354
High Similarity	0.8544	NPC471065
High Similarity	0.8544	NPC253015
High Similarity	0.8538	NPC469773
High Similarity	0.8538	NPC469775
High Similarity	0.8538	NPC469774
High Similarity	0.8538	NPC32723
High Similarity	0.8538	NPC469772
High Similarity	0.8538	NPC100925
High Similarity	0.8538	NPC469778
High Similarity	0.8538	NPC295941
High Similarity	0.8538	NPC135334
High Similarity	0.8538	NPC469776
High Similarity	0.8538	NPC469777
High Similarity	0.8538	NPC38438
High Similarity	0.8537	NPC186316
High Similarity	0.8537	NPC476065
High Similarity	0.8535	NPC40237
High Similarity	0.8535	NPC472714
High Similarity	0.8535	NPC5262
High Similarity	0.8535	NPC287124
High Similarity	0.8535	NPC151423
High Similarity	0.8529	NPC88557
High Similarity	0.8514	NPC473776
High Similarity	0.8514	NPC473205
High Similarity	0.8512	NPC121290
High Similarity	0.8509	NPC95392
High Similarity	0.8509	NPC44452
High Similarity	0.8509	NPC55715
High Similarity	0.8509	NPC35877
High Similarity	0.8503	NPC155754
High Similarity	0.8503	NPC124747
High Similarity	0.8503	NPC177100
High Similarity	0.8503	NPC139540
High Similarity	0.85	NPC39657
Intermediate Similarity	0.8497	NPC79736
Intermediate Similarity	0.8497	NPC67629
Intermediate Similarity	0.8497	NPC473713
Intermediate Similarity	0.8494	NPC215400
Intermediate Similarity	0.8494	NPC24339
Intermediate Similarity	0.8494	NPC166456
Intermediate Similarity	0.8494	NPC98083
Intermediate Similarity	0.8494	NPC230531
Intermediate Similarity	0.8494	NPC94220
Intermediate Similarity	0.8494	NPC7543
Intermediate Similarity	0.8488	NPC473550
Intermediate Similarity	0.8488	NPC316539
Intermediate Similarity	0.8485	NPC11411
Intermediate Similarity	0.8485	NPC165483
Intermediate Similarity	0.8481	NPC106920
Intermediate Similarity	0.8481	NPC477898
Intermediate Similarity	0.8481	NPC273657

Drug Structure

NPD7228 OpenBabel08211711362D 45 51 0 0 1 0 0 0 0 0999 V2000 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9889 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6665 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3902 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0593 2.2213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3956 1.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 -3.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 -3.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2 34 1 0 0 0 0 3 35 1 0 0 0 0 4 12 2 0 0 0 0 4 18 1 0 0 0 0 5 12 1 0 0 0 0 5 19 2 0 0 0 0 6 13 2 0 0 0 0 6 16 1 0 0 0 0 7 14 2 0 0 0 0 7 17 1 0 0 0 0 8 37 1 0 0 0 0 9 36 1 0 0 0 0 10 38 1 0 0 0 0 10 39 1 0 0 0 0 11 1 1 6 0 0 0 11 36 1 0 0 0 0 11 40 1 0 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 14 26 1 0 0 0 0 15 8 1 1 0 0 0 15 22 1 0 0 0 0 15 26 1 0 0 0 0 16 17 2 0 0 0 0 16 38 1 0 0 0 0 17 39 1 0 0 0 0 18 23 2 0 0 0 0 18 34 1 0 0 0 0 19 23 1 0 0 0 0 19 35 1 0 0 0 0 20 9 1 1 0 0 0 20 27 1 0 0 0 0 20 41 1 0 0 0 0 21 12 1 6 0 0 0 21 22 1 0 0 0 0 22 28 1 6 0 0 0 23 30 1 0 0 0 0 24 25 1 0 0 0 0 24 27 1 0 0 0 0 24 31 1 1 0 0 0 25 29 1 0 0 0 0 25 32 1 6 0 0 0 26 42 1 1 0 0 0 27 40 1 6 0 0 0 28 33 2 0 0 0 0 28 37 1 0 0 0 0 29 41 1 0 0 0 0 29 42 1 1 0 0 0 30 43 1 0 0 0 0 31 44 1 0 0 0 0 32 45 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DNAP001346; DAP000786
DrugBank	DB00773
ChEMBL	CHEMBL44657
IUPHAR/BPS	6815
PharmaGKB	PA449552
KEGG Drug	D00125
PubChem CID	36462
ChEBI	4911
CAS Number	33419-42-0

Drug Properties

Molecular Weight	588.18
ALogP	-2.5703
MLogP	3.22
XLogP	0.199
HDA	8
HBD	3
Rotatable Bonds	11
TPSA	160.83
RO5 Violation	0