NPASS drugs

Drug Information

Drug ID:	NPD5506
Drug Name:	Topotecan Hydrochloride
Molecular Formula:	C23H23N3O5.ClH
Canonical SMILES:	CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4ccc(c(c4cc3Cn1c2=O)CN(C)C)O.Cl
Standard InCHI:	InChI=1S/C23H23N3O5.ClH/c1-4-23(30)16-8-18-20-12(9-26(18)21(28)15(16)11-31-22(23)29)7-13-14(10-25(2)3)19(27)6-5-17(13)24-20;/h5-8,27,30H,4,9-11H2,1-3H3;1H/t23-;/m0./s1
Standard InCHIKey:	DGHHQBMTXTWTJV-BQAIUKQQSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD5506

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	251
0.1-0.2	1324
0.2-0.3	5473
0.3-0.4	7206
0.4-0.5	11811
0.5-0.6	3139
0.6-0.7	1537
0.7-0.8	140
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	3

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	0.9643	NPC74562
High Similarity	0.9643	NPC316181
High Similarity	0.9643	NPC151781
High Similarity	0.8889	NPC128115
High Similarity	0.8622	NPC129909
Intermediate Similarity	0.8333	NPC61435
Intermediate Similarity	0.8325	NPC192674
Intermediate Similarity	0.8325	NPC311858
Intermediate Similarity	0.8223	NPC470003
Intermediate Similarity	0.797	NPC14325
Intermediate Similarity	0.797	NPC28848
Intermediate Similarity	0.7628	NPC53344
Intermediate Similarity	0.7606	NPC211813
Intermediate Similarity	0.7581	NPC475841
Intermediate Similarity	0.7581	NPC474145
Intermediate Similarity	0.7558	NPC477548
Intermediate Similarity	0.7534	NPC472099
Intermediate Similarity	0.7534	NPC472098
Intermediate Similarity	0.7512	NPC249040
Intermediate Similarity	0.75	NPC472111
Intermediate Similarity	0.7489	NPC477549
Intermediate Similarity	0.7432	NPC469928
Intermediate Similarity	0.7431	NPC82548
Intermediate Similarity	0.7425	NPC470784
Intermediate Similarity	0.7425	NPC470785
Intermediate Similarity	0.7425	NPC474183
Intermediate Similarity	0.7414	NPC272549
Intermediate Similarity	0.7407	NPC200836
Intermediate Similarity	0.7386	NPC472435
Intermediate Similarity	0.7385	NPC270918
Intermediate Similarity	0.7382	NPC184680
Intermediate Similarity	0.7361	NPC295898
Intermediate Similarity	0.7358	NPC276517
Intermediate Similarity	0.7336	NPC470126
Intermediate Similarity	0.7336	NPC157931
Intermediate Similarity	0.7327	NPC476098
Intermediate Similarity	0.7325	NPC473449
Intermediate Similarity	0.7302	NPC280714
Intermediate Similarity	0.7298	NPC478010
Intermediate Similarity	0.7295	NPC472436
Intermediate Similarity	0.7277	NPC148183
Intermediate Similarity	0.7277	NPC152768
Intermediate Similarity	0.7256	NPC212213
Intermediate Similarity	0.7256	NPC239954
Intermediate Similarity	0.7253	NPC323752
Intermediate Similarity	0.7253	NPC323198
Intermediate Similarity	0.7248	NPC53144
Intermediate Similarity	0.7246	NPC475816
Intermediate Similarity	0.724	NPC174672
Intermediate Similarity	0.7237	NPC280272
Intermediate Similarity	0.7231	NPC189079
Intermediate Similarity	0.7229	NPC311906
Intermediate Similarity	0.7227	NPC88008
Intermediate Similarity	0.7222	NPC32200
Intermediate Similarity	0.722	NPC264176
Intermediate Similarity	0.7217	NPC214980
Intermediate Similarity	0.7209	NPC156704
Intermediate Similarity	0.7203	NPC82472
Intermediate Similarity	0.7193	NPC280799
Intermediate Similarity	0.719	NPC194040
Intermediate Similarity	0.719	NPC133609
Intermediate Similarity	0.7189	NPC315467
Intermediate Similarity	0.7188	NPC478074
Intermediate Similarity	0.7176	NPC168911
Intermediate Similarity	0.7175	NPC9894
Intermediate Similarity	0.7167	NPC14288
Intermediate Similarity	0.7162	NPC478141
Intermediate Similarity	0.7162	NPC469589
Intermediate Similarity	0.7161	NPC6786
Intermediate Similarity	0.716	NPC478009
Intermediate Similarity	0.7156	NPC66083
Intermediate Similarity	0.7155	NPC253580
Intermediate Similarity	0.7154	NPC478012
Intermediate Similarity	0.7149	NPC193238
Intermediate Similarity	0.7143	NPC24370
Intermediate Similarity	0.7143	NPC112206
Intermediate Similarity	0.7143	NPC48353
Intermediate Similarity	0.7143	NPC319232
Intermediate Similarity	0.7143	NPC202605
Intermediate Similarity	0.7143	NPC99891
Intermediate Similarity	0.7137	NPC475720
Intermediate Similarity	0.7137	NPC474192
Intermediate Similarity	0.7137	NPC96321
Intermediate Similarity	0.713	NPC474188
Intermediate Similarity	0.7125	NPC472434
Intermediate Similarity	0.7123	NPC183805
Intermediate Similarity	0.7123	NPC128751
Intermediate Similarity	0.7123	NPC246700
Intermediate Similarity	0.7119	NPC473800
Intermediate Similarity	0.7117	NPC287208
Intermediate Similarity	0.7112	NPC118559
Intermediate Similarity	0.7112	NPC304307
Intermediate Similarity	0.7112	NPC34580
Intermediate Similarity	0.7112	NPC124920
Intermediate Similarity	0.7112	NPC257851
Intermediate Similarity	0.7102	NPC478080
Intermediate Similarity	0.7095	NPC469734
Intermediate Similarity	0.7093	NPC469727
Intermediate Similarity	0.7091	NPC223427
Intermediate Similarity	0.7089	NPC106833
Intermediate Similarity	0.7089	NPC469497
Intermediate Similarity	0.7085	NPC174758
Intermediate Similarity	0.7085	NPC476116
Intermediate Similarity	0.7085	NPC478006
Intermediate Similarity	0.7082	NPC100547
Intermediate Similarity	0.7076	NPC94428
Intermediate Similarity	0.7076	NPC263937
Intermediate Similarity	0.7072	NPC193777
Intermediate Similarity	0.707	NPC198673
Intermediate Similarity	0.7061	NPC469594
Intermediate Similarity	0.7061	NPC303658
Intermediate Similarity	0.7059	NPC475070
Intermediate Similarity	0.7059	NPC118832
Intermediate Similarity	0.7059	NPC47059
Intermediate Similarity	0.7059	NPC165349
Intermediate Similarity	0.7059	NPC329708
Intermediate Similarity	0.7059	NPC264166
Intermediate Similarity	0.7059	NPC274291
Intermediate Similarity	0.7056	NPC65277
Intermediate Similarity	0.7054	NPC85273
Intermediate Similarity	0.7054	NPC260909
Intermediate Similarity	0.7054	NPC471304
Intermediate Similarity	0.7051	NPC95240
Intermediate Similarity	0.7051	NPC322135
Intermediate Similarity	0.7051	NPC153042
Intermediate Similarity	0.7051	NPC90229
Intermediate Similarity	0.7051	NPC223409
Intermediate Similarity	0.7049	NPC181081
Intermediate Similarity	0.7048	NPC330009
Intermediate Similarity	0.7039	NPC261251
Intermediate Similarity	0.7035	NPC471080
Intermediate Similarity	0.7035	NPC469592
Intermediate Similarity	0.7034	NPC284888
Intermediate Similarity	0.7033	NPC303374
Intermediate Similarity	0.7031	NPC313804
Intermediate Similarity	0.7031	NPC315804
Intermediate Similarity	0.7031	NPC17565
Intermediate Similarity	0.7026	NPC21638
Intermediate Similarity	0.7024	NPC65080
Intermediate Similarity	0.7021	NPC477531
Intermediate Similarity	0.702	NPC478011
Intermediate Similarity	0.7014	NPC320394
Intermediate Similarity	0.7013	NPC220851
Intermediate Similarity	0.7013	NPC118121
Intermediate Similarity	0.7009	NPC471762
Intermediate Similarity	0.7009	NPC194740
Intermediate Similarity	0.7009	NPC252251
Intermediate Similarity	0.7009	NPC201697
Intermediate Similarity	0.7004	NPC279589
Remote Similarity	0.6996	NPC214142
Remote Similarity	0.6992	NPC321592
Remote Similarity	0.6992	NPC314882
Remote Similarity	0.6992	NPC329982
Remote Similarity	0.6992	NPC54803
Remote Similarity	0.6992	NPC314176
Remote Similarity	0.6991	NPC230403
Remote Similarity	0.6991	NPC235900
Remote Similarity	0.6987	NPC173080
Remote Similarity	0.698	NPC67401
Remote Similarity	0.6979	NPC209174
Remote Similarity	0.6978	NPC5145
Remote Similarity	0.6977	NPC45048
Remote Similarity	0.6971	NPC473540
Remote Similarity	0.6968	NPC123019
Remote Similarity	0.6967	NPC176127
Remote Similarity	0.6965	NPC237901
Remote Similarity	0.6965	NPC195788
Remote Similarity	0.6964	NPC470931
Remote Similarity	0.6962	NPC141053
Remote Similarity	0.696	NPC266931
Remote Similarity	0.6959	NPC57994
Remote Similarity	0.6959	NPC289299
Remote Similarity	0.6958	NPC41501
Remote Similarity	0.6957	NPC471294
Remote Similarity	0.6957	NPC74360
Remote Similarity	0.6955	NPC329793
Remote Similarity	0.6955	NPC315491
Remote Similarity	0.6955	NPC45459
Remote Similarity	0.6951	NPC304183
Remote Similarity	0.6951	NPC277350
Remote Similarity	0.6948	NPC171171
Remote Similarity	0.6948	NPC284685
Remote Similarity	0.6946	NPC476995
Remote Similarity	0.6943	NPC305984
Remote Similarity	0.6941	NPC306376
Remote Similarity	0.6933	NPC245055
Remote Similarity	0.6933	NPC33064
Remote Similarity	0.693	NPC471284
Remote Similarity	0.6929	NPC477066
Remote Similarity	0.6929	NPC475844
Remote Similarity	0.6927	NPC245916
Remote Similarity	0.6926	NPC61813
Remote Similarity	0.6923	NPC471944
Remote Similarity	0.692	NPC474905
Remote Similarity	0.692	NPC314297
Remote Similarity	0.692	NPC89549
Remote Similarity	0.692	NPC315545
Remote Similarity	0.6916	NPC296482
Remote Similarity	0.6916	NPC53069
Remote Similarity	0.6916	NPC202768

Drug Structure

NPD5506 OpenBabel08211708292D 34 37 0 0 1 0 0 0 0 0999 V2000 7.3872 -1.3770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9686 -5.1989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0910 -6.7183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4002 -1.3772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2146 -2.2533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3778 -2.7362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8871 -4.1857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2337 -2.2545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5599 -4.1860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2140 -5.1986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9062 -4.1869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7239 -3.7030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0510 -3.7027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2142 -4.1856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0696 -3.7037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0697 -2.7375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0512 -2.7365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3969 -2.7372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3776 -3.7023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7241 -2.7368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2333 -4.1863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7432 -2.7378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9066 -2.2546 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8875 -2.2538 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.0912 -5.7053 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.3967 -3.7033 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5002 -4.2087 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2331 -5.1863 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.6206 -2.2315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4132 -1.3774 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7430 -3.7040 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0657 -1.4623 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -5.2217 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9069 -0.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 5 6 1 0 0 0 0 5 17 2 0 0 0 0 6 19 2 0 0 0 0 7 12 2 0 0 0 0 7 13 1 0 0 0 0 8 16 1 0 0 0 0 8 18 2 0 0 0 0 9 12 1 0 0 0 0 9 26 1 0 0 0 0 10 14 1 0 0 0 0 10 25 1 0 0 0 0 11 15 1 0 0 0 0 11 31 1 0 0 0 0 12 20 1 0 0 0 0 13 14 2 0 0 0 0 13 17 1 0 0 0 0 14 19 1 0 0 0 0 15 16 2 0 0 0 0 15 21 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 20 1 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 24 2 0 0 0 0 21 26 1 0 0 0 0 21 28 2 0 0 0 0 22 23 1 0 0 0 0 22 29 2 0 0 0 0 22 31 1 0 0 0 0 23 4 1 1 0 0 0 23 30 1 0 0 0 0 27 33 1 0 0 0 0 30 34 1 0 0 0 0 M END $$$$

External Identifiers

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

Drug Properties

Molecular Weight	421.16
ALogP	-1.8179
MLogP	3.11
XLogP	0.501
HDA	7
HBD	2
Rotatable Bonds	8
TPSA	103.2
RO5 Violation	0