NPASS drugs

Drug Information

Drug ID:	NPD6392
Drug Name:	Fosamprenavir
Molecular Formula:	C25H36N3O9PS
Canonical SMILES:	CC(CN(S(=O)(=O)c1ccc(cc1)N)C[C@H]([C@H](Cc1ccccc1)N=C(O[C@H]1CCOC1)O)OP(=O)(O)O)C
Standard InCHI:	InChI=1S/C25H36N3O9PS/c1-18(2)15-28(39(33,34)22-10-8-20(26)9-11-22)16-24(37-38(30,31)32)23(14-19-6-4-3-5-7-19)27-25(29)36-21-12-13-35-17-21/h3-11,18,21,23-24H,12-17,26H2,1-2H3,(H,27,29)(H2,30,31,32)/t21-,23-,24+/m0/s1
Standard InCHIKey:	MLBVMOWEQCZNCC-OEMFJLHTSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD6392

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	114
0.1-0.2	886
0.2-0.3	4845
0.3-0.4	15900
0.4-0.5	7758
0.5-0.6	1368
0.6-0.7	19
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 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
Remote Similarity	0.6582	NPC101372
Remote Similarity	0.6488	NPC477556
Remote Similarity	0.6235	NPC472103
Remote Similarity	0.6084	NPC313352
Remote Similarity	0.6076	NPC477061
Remote Similarity	0.6076	NPC45777
Remote Similarity	0.6071	NPC477557
Remote Similarity	0.6065	NPC101139
Remote Similarity	0.6061	NPC194857
Remote Similarity	0.6061	NPC32858
Remote Similarity	0.6047	NPC311330
Remote Similarity	0.6039	NPC313640
Remote Similarity	0.6023	NPC286551
Remote Similarity	0.6022	NPC85651
Remote Similarity	0.6011	NPC206372
Remote Similarity	0.6011	NPC203424
Remote Similarity	0.6	NPC321617
Remote Similarity	0.6	NPC7817
Remote Similarity	0.6	NPC475168
Remote Similarity	0.5977	NPC472100
Remote Similarity	0.5976	NPC287358
Remote Similarity	0.5962	NPC218710
Remote Similarity	0.5928	NPC46413
Remote Similarity	0.5917	NPC127741
Remote Similarity	0.5912	NPC471527
Remote Similarity	0.5906	NPC243162
Remote Similarity	0.5901	NPC252878
Remote Similarity	0.5899	NPC470902
Remote Similarity	0.5886	NPC264589
Remote Similarity	0.5886	NPC254088
Remote Similarity	0.5872	NPC161069
Remote Similarity	0.5872	NPC316202
Remote Similarity	0.5867	NPC88267
Remote Similarity	0.5867	NPC113326
Remote Similarity	0.5867	NPC194390
Remote Similarity	0.5867	NPC224610
Remote Similarity	0.5864	NPC283130
Remote Similarity	0.5864	NPC46427
Remote Similarity	0.5864	NPC35996
Remote Similarity	0.5864	NPC328683
Remote Similarity	0.5852	NPC254798
Remote Similarity	0.5849	NPC237420
Remote Similarity	0.5847	NPC35510
Remote Similarity	0.5847	NPC471053
Remote Similarity	0.5847	NPC253667
Remote Similarity	0.5847	NPC471051
Remote Similarity	0.5847	NPC471052
Remote Similarity	0.5845	NPC315403
Remote Similarity	0.5843	NPC122590
Remote Similarity	0.5838	NPC300631
Remote Similarity	0.5833	NPC477159
Remote Similarity	0.5829	NPC116519
Remote Similarity	0.5829	NPC470824
Remote Similarity	0.5824	NPC68865
Remote Similarity	0.5818	NPC476950
Remote Similarity	0.5815	NPC189116
Remote Similarity	0.5805	NPC314287
Remote Similarity	0.5801	NPC477157
Remote Similarity	0.5801	NPC63370
Remote Similarity	0.5801	NPC477156
Remote Similarity	0.5801	NPC36836
Remote Similarity	0.5795	NPC105717
Remote Similarity	0.5793	NPC325013
Remote Similarity	0.5786	NPC169328
Remote Similarity	0.5776	NPC476990
Remote Similarity	0.5765	NPC316405
Remote Similarity	0.5763	NPC212799
Remote Similarity	0.5761	NPC472121
Remote Similarity	0.5759	NPC475094
Remote Similarity	0.5754	NPC314223
Remote Similarity	0.575	NPC310467
Remote Similarity	0.575	NPC314992
Remote Similarity	0.5744	NPC291759
Remote Similarity	0.5741	NPC71684
Remote Similarity	0.5741	NPC202521
Remote Similarity	0.5739	NPC138775
Remote Similarity	0.5733	NPC291610
Remote Similarity	0.573	NPC139506
Remote Similarity	0.573	NPC311276
Remote Similarity	0.573	NPC292143
Remote Similarity	0.5723	NPC470544
Remote Similarity	0.5723	NPC478079
Remote Similarity	0.5723	NPC2265
Remote Similarity	0.5723	NPC89923
Remote Similarity	0.5723	NPC147957
Remote Similarity	0.5723	NPC239990
Remote Similarity	0.5723	NPC152850
Remote Similarity	0.5723	NPC105114
Remote Similarity	0.5723	NPC71933
Remote Similarity	0.5722	NPC469462
Remote Similarity	0.5714	NPC209509
Remote Similarity	0.5714	NPC322878
Remote Similarity	0.5714	NPC25565
Remote Similarity	0.5707	NPC309531
Remote Similarity	0.5707	NPC472102
Remote Similarity	0.5699	NPC52059
Remote Similarity	0.5699	NPC470069
Remote Similarity	0.5697	NPC47667
Remote Similarity	0.5696	NPC205652
Remote Similarity	0.5696	NPC470550
Remote Similarity	0.5692	NPC133591
Remote Similarity	0.569	NPC83289
Remote Similarity	0.569	NPC212850
Remote Similarity	0.569	NPC189724
Remote Similarity	0.5689	NPC328590
Remote Similarity	0.5687	NPC470545
Remote Similarity	0.5684	NPC189812
Remote Similarity	0.5684	NPC329688
Remote Similarity	0.5684	NPC477462
Remote Similarity	0.5683	NPC153694
Remote Similarity	0.5683	NPC211525
Remote Similarity	0.5682	NPC262077
Remote Similarity	0.568	NPC476687
Remote Similarity	0.568	NPC476685
Remote Similarity	0.568	NPC476689
Remote Similarity	0.5676	NPC475439
Remote Similarity	0.5676	NPC473501
Remote Similarity	0.5674	NPC2501
Remote Similarity	0.5671	NPC6975
Remote Similarity	0.567	NPC139291
Remote Similarity	0.567	NPC472110
Remote Similarity	0.567	NPC472109
Remote Similarity	0.567	NPC472108
Remote Similarity	0.5667	NPC475763
Remote Similarity	0.5665	NPC239762
Remote Similarity	0.5665	NPC163392
Remote Similarity	0.5663	NPC136453
Remote Similarity	0.5663	NPC477937
Remote Similarity	0.5661	NPC83241
Remote Similarity	0.5659	NPC311357
Remote Similarity	0.5659	NPC473297
Remote Similarity	0.5657	NPC476978
Remote Similarity	0.5655	NPC226662
Remote Similarity	0.5652	NPC470546
Remote Similarity	0.5652	NPC97380
Remote Similarity	0.5652	NPC263709
Remote Similarity	0.5652	NPC63210
Remote Similarity	0.5652	NPC310403
Remote Similarity	0.5652	NPC148468
Remote Similarity	0.5652	NPC243673
Remote Similarity	0.565	NPC145113
Remote Similarity	0.5648	NPC11149
Remote Similarity	0.5646	NPC58674
Remote Similarity	0.564	NPC471265
Remote Similarity	0.564	NPC478140
Remote Similarity	0.564	NPC471264
Remote Similarity	0.5633	NPC1986
Remote Similarity	0.5633	NPC474544
Remote Similarity	0.5632	NPC225381
Remote Similarity	0.5632	NPC285622
Remote Similarity	0.5632	NPC168113
Remote Similarity	0.5629	NPC319766
Remote Similarity	0.5628	NPC297145
Remote Similarity	0.5628	NPC197743
Remote Similarity	0.5625	NPC478040
Remote Similarity	0.5625	NPC5620
Remote Similarity	0.5625	NPC315266
Remote Similarity	0.5622	NPC73655
Remote Similarity	0.5622	NPC68650
Remote Similarity	0.5622	NPC320064
Remote Similarity	0.5621	NPC314473
Remote Similarity	0.5621	NPC157311
Remote Similarity	0.5618	NPC471821
Remote Similarity	0.5618	NPC471820
Remote Similarity	0.5615	NPC472106
Remote Similarity	0.5612	NPC52262
Remote Similarity	0.561	NPC472330
Remote Similarity	0.561	NPC472329
Remote Similarity	0.5608	NPC317400
Remote Similarity	0.5607	NPC77992
Remote Similarity	0.5606	NPC284706
Remote Similarity	0.5604	NPC469903
Remote Similarity	0.5602	NPC474847
Remote Similarity	0.5602	NPC95412
Remote Similarity	0.56	NPC314113
Remote Similarity	0.56	NPC197682
Remote Similarity	0.56	NPC176226

Drug Structure

NPD6392 OpenBabel08211709092D 44 46 0 0 1 0 0 0 0 0999 V2000 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0981 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0981 -3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0981 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0981 -3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4071 -6.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -7.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7891 -6.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -5.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5981 -2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 -7.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -7.0981 -1.6340 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0981 -3.3660 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 19 2 0 0 0 0 7 19 1 0 0 0 0 8 10 1 0 0 0 0 8 20 2 0 0 0 0 9 11 2 0 0 0 0 9 20 1 0 0 0 0 10 22 2 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 21 1 0 0 0 0 13 35 1 0 0 0 0 14 19 1 0 0 0 0 15 18 1 0 0 0 0 15 28 1 0 0 0 0 16 28 1 0 0 0 0 17 21 1 0 0 0 0 17 35 1 0 0 0 0 20 26 1 0 0 0 0 21 36 1 6 0 0 0 22 39 1 0 0 0 0 23 14 1 6 0 0 0 23 24 1 0 0 0 0 23 27 1 0 0 0 0 24 16 1 1 0 0 0 24 37 1 0 0 0 0 25 27 2 3 0 0 0 25 29 1 0 0 0 0 25 36 1 0 0 0 0 26 40 1 0 0 0 0 26 41 1 0 0 0 0 28 39 1 0 0 0 0 29 42 1 0 0 0 0 30 38 1 0 0 0 0 30 43 1 0 0 0 0 31 38 1 0 0 0 0 31 44 1 0 0 0 0 32 38 2 0 0 0 0 33 39 2 0 0 0 0 34 39 2 0 0 0 0 37 38 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000707
DrugBank	DB01319
ChEMBL	CHEMBL1664
IUPHAR/BPS
PharmaGKB	PA10084
KEGG Drug
PubChem CID	131536
ChEBI	82941
CAS Number	226700-79-4

Drug Properties

Molecular Weight	585.19
ALogP	-1.637
MLogP	2.67
XLogP	3.531
HDA	12
HBD	4
Rotatable Bonds	20
TPSA	199.4
RO5 Violation	2