NPASS drugs

Drug Information

Drug ID:	NPD5699
Drug Name:	Estramustine
Molecular Formula:	C23H31Cl2NO3
Canonical SMILES:	ClCCN(C(=O)Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C)CCCl
Standard InCHI:	"InChI=1S/C23H31Cl2NO3/c1-23-9-8-18-17-5-3-16(29-22(28)26(12-10-24)13-11-25)14-15(17)2-4-19(18)20(23)6-7-21(23)27/h3,5,14,18-21,27H,2,4,6-13H2,1H3/t18-,19-,20+,21+,23+/m1/s1"
Standard InCHIKey:	FRPJXPJMRWBBIH-RBRWEJTLSA-N
Max Developmental Stage:	Phase 3
Max Developmental Stage Source:	TTD; DrugBank; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD5699

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	42390
0.1-0.2	165906
0.2-0.3	3362
0.3-0.4	53
0.4-0.5	15
0.5-0.6	14
0.6-0.7	0
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	0.5921	NPC89650
Remote Similarity	0.5833	NPC327694
Remote Similarity	0.5753	NPC324822
Remote Similarity	0.5616	NPC321502
Remote Similarity	0.5616	NPC611227
Remote Similarity	0.5417	NPC48342
Remote Similarity	0.5417	NPC294638
Remote Similarity	0.5417	NPC328831
Remote Similarity	0.5417	NPC164649
Remote Similarity	0.5417	NPC290287
Remote Similarity	0.5417	NPC601860
Remote Similarity	0.5417	NPC609599
Remote Similarity	0.5405	NPC220771
Remote Similarity	0.5211	NPC321402

Drug Structure

NPD5699 OpenBabel08211708292D 30 33 0 0 1 0 0 0 0 0999 V2000 -0.0003 1.0131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6942 -2.9318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2326 -1.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8474 -2.4432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3864 -0.9761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6919 -0.9775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6922 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6933 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8465 0.4890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6186 -4.3950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4642 -2.9290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7722 -3.9068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6178 -2.4408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3869 -2.9313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5407 -2.4427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2329 -2.4422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5404 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6936 -0.9765 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8471 -1.4656 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9770 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8468 0.4886 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9253 -2.4415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4646 -3.9061 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 9.3102 -2.4401 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 6.7717 -2.9297 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8474 1.4652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9249 -1.4644 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0793 -2.9304 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5735 2.1182 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2 4 1 0 0 0 0 2 15 1 0 0 0 0 3 5 1 0 0 0 0 3 16 2 0 0 0 0 5 17 2 0 0 0 0 6 7 1 0 0 0 0 6 20 1 0 0 0 0 7 21 1 0 0 0 0 8 9 1 0 0 0 0 9 23 1 0 0 0 0 10 12 1 0 0 0 0 10 24 1 0 0 0 0 11 13 1 0 0 0 0 11 25 1 0 0 0 0 12 26 1 0 0 0 0 13 26 1 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 29 1 0 0 0 0 17 18 1 0 0 0 0 18 8 1 6 0 0 0 18 19 1 0 0 0 0 19 4 1 1 0 0 0 19 20 1 0 0 0 0 20 23 1 6 0 0 0 21 23 1 6 0 0 0 21 27 1 0 0 0 0 22 26 1 0 0 0 0 22 28 2 0 0 0 0 22 29 1 0 0 0 0 23 1 1 6 0 0 0 27 30 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP001307
DrugBank	DB01196
ChEMBL	CHEMBL1575
IUPHAR/BPS	9076
PharmaGKB	PA449507
KEGG Drug	D04066
PubChem CID	259331
ChEBI	4868
CAS Number	2998-57-4

Drug Properties

Molecular Weight	439.17
ALogP	1.4414
MLogP	3.33
XLogP	6.698
HDA	3
HBD	1
Rotatable Bonds	11
TPSA	49.77
RO5 Violation	1