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 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	95182
0.1-0.2	115415
0.2-0.3	1114
0.3-0.4	5
0.4-0.5	4
0.5-0.6	3
0.6-0.7	17
0.7-0.8	0
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
Remote Similarity	0.6905	NPC316181
Remote Similarity	0.6905	NPC151781
Remote Similarity	0.6905	NPC599830
Remote Similarity	0.6588	NPC192674
Remote Similarity	0.6588	NPC599867
Remote Similarity	0.6517	NPC74562
Remote Similarity	0.6512	NPC267229
Remote Similarity	0.6364	NPC276661
Remote Similarity	0.6364	NPC599818
Remote Similarity	0.6353	NPC129909
Remote Similarity	0.6353	NPC606011
Remote Similarity	0.6322	NPC128115
Remote Similarity	0.6322	NPC42856
Remote Similarity	0.6279	NPC106338
Remote Similarity	0.6279	NPC303320
Remote Similarity	0.6279	NPC541875
Remote Similarity	0.6279	NPC608071
Remote Similarity	0.5667	NPC90909
Remote Similarity	0.5143	NPC556976
Remote Similarity	0.5046	NPC197381

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	0
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