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:	Approved
Max Developmental Stage Source:	TTD; DrugBank; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD5699

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	134
0.1-0.2	1088
0.2-0.3	2074
0.3-0.4	6791
0.4-0.5	7299
0.5-0.6	10065
0.6-0.7	3385
0.7-0.8	54
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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
Intermediate Similarity	0.7667	NPC321502
Intermediate Similarity	0.7606	NPC164649
Intermediate Similarity	0.7606	NPC48342
Intermediate Similarity	0.7589	NPC33900
Intermediate Similarity	0.7586	NPC152946
Intermediate Similarity	0.7533	NPC249425
Intermediate Similarity	0.7448	NPC328504
Intermediate Similarity	0.7434	NPC325568
Intermediate Similarity	0.7432	NPC4286
Intermediate Similarity	0.7432	NPC76119
Intermediate Similarity	0.7397	NPC77569
Intermediate Similarity	0.7397	NPC142198
Intermediate Similarity	0.7333	NPC186889
Intermediate Similarity	0.732	NPC85595
Intermediate Similarity	0.726	NPC321133
Intermediate Similarity	0.723	NPC321402
Intermediate Similarity	0.719	NPC196193
Intermediate Similarity	0.7178	NPC95990
Intermediate Similarity	0.7143	NPC68339
Intermediate Similarity	0.7143	NPC260832
Intermediate Similarity	0.7143	NPC135467
Intermediate Similarity	0.7143	NPC103916
Intermediate Similarity	0.7124	NPC288290
Intermediate Similarity	0.7113	NPC322753
Intermediate Similarity	0.711	NPC476751
Intermediate Similarity	0.7107	NPC221134
Intermediate Similarity	0.7105	NPC30491
Intermediate Similarity	0.7105	NPC262936
Intermediate Similarity	0.7103	NPC312105
Intermediate Similarity	0.7103	NPC247858
Intermediate Similarity	0.7103	NPC137496
Intermediate Similarity	0.7103	NPC154511
Intermediate Similarity	0.7103	NPC474387
Intermediate Similarity	0.7103	NPC474358
Intermediate Similarity	0.7103	NPC257540
Intermediate Similarity	0.7099	NPC271607
Intermediate Similarity	0.7099	NPC280717
Intermediate Similarity	0.7099	NPC235195
Intermediate Similarity	0.7099	NPC19862
Intermediate Similarity	0.707	NPC252343
Intermediate Similarity	0.7067	NPC255253
Intermediate Similarity	0.7059	NPC277458
Intermediate Similarity	0.7059	NPC471396
Intermediate Similarity	0.7059	NPC307050
Intermediate Similarity	0.7059	NPC223912
Intermediate Similarity	0.7059	NPC176590
Intermediate Similarity	0.7047	NPC475166
Intermediate Similarity	0.7034	NPC147179
Intermediate Similarity	0.703	NPC273358
Intermediate Similarity	0.703	NPC298647
Intermediate Similarity	0.7027	NPC99734
Intermediate Similarity	0.7006	NPC11266
Intermediate Similarity	0.7006	NPC213122
Intermediate Similarity	0.7	NPC30462
Remote Similarity	0.6986	NPC38893
Remote Similarity	0.6986	NPC219112
Remote Similarity	0.6986	NPC477137
Remote Similarity	0.6986	NPC308828
Remote Similarity	0.6986	NPC308311
Remote Similarity	0.6981	NPC150712
Remote Similarity	0.6974	NPC29008
Remote Similarity	0.6974	NPC228771
Remote Similarity	0.6974	NPC266705
Remote Similarity	0.697	NPC32017
Remote Similarity	0.697	NPC96930
Remote Similarity	0.6966	NPC268160
Remote Similarity	0.6957	NPC138149
Remote Similarity	0.6943	NPC227719
Remote Similarity	0.6939	NPC477136
Remote Similarity	0.6939	NPC25648
Remote Similarity	0.6937	NPC76032
Remote Similarity	0.6937	NPC132723
Remote Similarity	0.6933	NPC327623
Remote Similarity	0.6928	NPC292206
Remote Similarity	0.6928	NPC269598
Remote Similarity	0.6928	NPC470724
Remote Similarity	0.6928	NPC218323
Remote Similarity	0.6923	NPC474200
Remote Similarity	0.6923	NPC153019
Remote Similarity	0.6918	NPC476699
Remote Similarity	0.6918	NPC192948
Remote Similarity	0.6918	NPC35797
Remote Similarity	0.6914	NPC20631
Remote Similarity	0.6914	NPC93640
Remote Similarity	0.6913	NPC318552
Remote Similarity	0.6913	NPC190501
Remote Similarity	0.6908	NPC265413
Remote Similarity	0.6908	NPC111088
Remote Similarity	0.6908	NPC10154
Remote Similarity	0.6908	NPC75432
Remote Similarity	0.6903	NPC126859
Remote Similarity	0.6903	NPC259665
Remote Similarity	0.6903	NPC89769
Remote Similarity	0.6899	NPC471942
Remote Similarity	0.6892	NPC474040
Remote Similarity	0.6892	NPC469609
Remote Similarity	0.6892	NPC471671
Remote Similarity	0.6887	NPC478058
Remote Similarity	0.6887	NPC476332
Remote Similarity	0.6887	NPC473464
Remote Similarity	0.6886	NPC208785
Remote Similarity	0.6886	NPC470619
Remote Similarity	0.6886	NPC470618
Remote Similarity	0.6886	NPC145527
Remote Similarity	0.6883	NPC66177
Remote Similarity	0.6883	NPC8305
Remote Similarity	0.6883	NPC268763
Remote Similarity	0.6883	NPC471077
Remote Similarity	0.6879	NPC27578
Remote Similarity	0.6879	NPC227002
Remote Similarity	0.6879	NPC289624
Remote Similarity	0.6875	NPC131198
Remote Similarity	0.6871	NPC469663
Remote Similarity	0.6871	NPC92
Remote Similarity	0.6867	NPC129176
Remote Similarity	0.6863	NPC470726
Remote Similarity	0.6863	NPC124030
Remote Similarity	0.6863	NPC9067
Remote Similarity	0.6863	NPC17348
Remote Similarity	0.6853	NPC474272
Remote Similarity	0.6852	NPC29599
Remote Similarity	0.6848	NPC471608
Remote Similarity	0.6846	NPC42657
Remote Similarity	0.6846	NPC469644
Remote Similarity	0.6845	NPC261659
Remote Similarity	0.6845	NPC26601
Remote Similarity	0.6839	NPC201069
Remote Similarity	0.6839	NPC124802
Remote Similarity	0.6835	NPC211352
Remote Similarity	0.6829	NPC145304
Remote Similarity	0.6826	NPC274026
Remote Similarity	0.6826	NPC253591
Remote Similarity	0.6824	NPC147091
Remote Similarity	0.6824	NPC172219
Remote Similarity	0.6824	NPC304510
Remote Similarity	0.6821	NPC233650
Remote Similarity	0.6818	NPC170485
Remote Similarity	0.6818	NPC128321
Remote Similarity	0.6815	NPC258073
Remote Similarity	0.6813	NPC68292
Remote Similarity	0.6813	NPC193528
Remote Similarity	0.681	NPC35212
Remote Similarity	0.6802	NPC471394
Remote Similarity	0.6802	NPC293164
Remote Similarity	0.68	NPC327694
Remote Similarity	0.6797	NPC474532
Remote Similarity	0.6797	NPC248557
Remote Similarity	0.6795	NPC206028
Remote Similarity	0.6795	NPC86257
Remote Similarity	0.6792	NPC311256
Remote Similarity	0.679	NPC470925
Remote Similarity	0.679	NPC275150
Remote Similarity	0.6788	NPC307205
Remote Similarity	0.6784	NPC129603
Remote Similarity	0.6783	NPC11554
Remote Similarity	0.6783	NPC201959
Remote Similarity	0.6783	NPC75440
Remote Similarity	0.6782	NPC134858
Remote Similarity	0.6779	NPC474214
Remote Similarity	0.6774	NPC177167
Remote Similarity	0.677	NPC231572
Remote Similarity	0.6768	NPC252133
Remote Similarity	0.6768	NPC310621
Remote Similarity	0.6765	NPC105942
Remote Similarity	0.6765	NPC205392
Remote Similarity	0.6761	NPC318472
Remote Similarity	0.6759	NPC470723
Remote Similarity	0.6752	NPC470727
Remote Similarity	0.675	NPC167944
Remote Similarity	0.675	NPC42793
Remote Similarity	0.675	NPC231884
Remote Similarity	0.6748	NPC473612
Remote Similarity	0.6747	NPC253883
Remote Similarity	0.6747	NPC90844
Remote Similarity	0.6747	NPC95075
Remote Similarity	0.6746	NPC270811
Remote Similarity	0.6746	NPC471073
Remote Similarity	0.6744	NPC67080
Remote Similarity	0.6735	NPC470837
Remote Similarity	0.6733	NPC474320
Remote Similarity	0.6732	NPC320287
Remote Similarity	0.6731	NPC47288
Remote Similarity	0.6731	NPC283079
Remote Similarity	0.6728	NPC234548
Remote Similarity	0.6728	NPC265335
Remote Similarity	0.6728	NPC248287
Remote Similarity	0.6728	NPC116742
Remote Similarity	0.6728	NPC139243
Remote Similarity	0.6727	NPC185838
Remote Similarity	0.6726	NPC146388
Remote Similarity	0.6712	NPC228425
Remote Similarity	0.6711	NPC475839
Remote Similarity	0.671	NPC206882
Remote Similarity	0.6709	NPC118419
Remote Similarity	0.6708	NPC318591
Remote Similarity	0.6708	NPC231163
Remote Similarity	0.6707	NPC476336
Remote Similarity	0.6705	NPC150879
Remote Similarity	0.6705	NPC97072
Remote Similarity	0.6705	NPC215829

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