NPASS drugs

Drug Information

Drug ID:	NPD5507
Drug Name:	Topotecan
Molecular Formula:	C23H23N3O5
Canonical SMILES:	CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4ccc(c(c4cc3Cn1c2=O)CN(C)C)O
Standard InCHI:	"InChI=1S/C23H23N3O5/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/t23-/m0/s1"
Standard InCHIKey:	UCFGDBYHRUNTLO-QHCPKHFHSA-N
Max Developmental Stage:	Phase 4
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD5507

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	94689
0.1-0.2	115815
0.2-0.3	1207
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	0.6988	NPC316181
Remote Similarity	0.6988	NPC151781
Remote Similarity	0.6988	NPC599830
Remote Similarity	0.6667	NPC192674
Remote Similarity	0.6667	NPC599867
Remote Similarity	0.6591	NPC74562
Remote Similarity	0.6588	NPC267229
Remote Similarity	0.6437	NPC276661
Remote Similarity	0.6437	NPC599818
Remote Similarity	0.6429	NPC129909
Remote Similarity	0.6429	NPC606011
Remote Similarity	0.6395	NPC128115
Remote Similarity	0.6395	NPC42856
Remote Similarity	0.6353	NPC106338
Remote Similarity	0.6353	NPC303320
Remote Similarity	0.6353	NPC541875
Remote Similarity	0.6353	NPC608071
Remote Similarity	0.573	NPC90909
Remote Similarity	0.5192	NPC556976
Remote Similarity	0.5093	NPC197381

Drug Structure

NPD5507 OpenBabel08211708292D 33 37 0 0 1 0 0 0 0 0999 V2000 -2.3558 2.3270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7744 -1.4949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6520 -3.0143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3428 2.3268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5284 1.4507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3652 0.9678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8559 -0.4817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5093 1.4495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1830 -0.4820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5290 -1.4946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8368 -0.4829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0191 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6920 0.0013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5288 -0.4816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6734 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6732 0.9665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6918 0.9675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3461 0.9668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3654 0.0017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0189 0.9672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5097 -0.4823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 0.9662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 1.4494 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8555 1.4502 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.6518 -2.0013 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3463 0.0007 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -9.2428 -0.5047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5099 -1.4823 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8776 1.4725 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3297 2.3266 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 -9.2430 -1.5177 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8361 3.2040 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 32 1 0 0 0 0 30 33 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP001449; DAP000648
DrugBank	DB01030
ChEMBL	CHEMBL84
IUPHAR/BPS	7101
PharmaGKB	PA451729
KEGG Drug
PubChem CID	60700
ChEBI	63632
CAS Number	123948-87-8

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