NPASS drugs

Drug Information

Drug ID:	NPD6378
Drug Name:	Amprenavir
Molecular Formula:	C25H35N3O6S
Canonical SMILES:	CC(CN(S(=O)(=O)c1ccc(cc1)N)C[C@H]([C@H](Cc1ccccc1)N=C(O[C@H]1CCOC1)O)O)C
Standard InCHI:	InChI=1S/C25H35N3O6S/c1-18(2)15-28(35(31,32)22-10-8-20(26)9-11-22)16-24(29)23(14-19-6-4-3-5-7-19)27-25(30)34-21-12-13-33-17-21/h3-11,18,21,23-24,29H,12-17,26H2,1-2H3,(H,27,30)/t21-,23-,24+/m0/s1
Standard InCHIKey:	YMARZQAQMVYCKC-OEMFJLHTSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD6378

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	101
0.1-0.2	775
0.2-0.3	3145
0.3-0.4	15347
0.4-0.5	9387
0.5-0.6	2048
0.6-0.7	86
0.7-0.8	1
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	0.702	NPC101372
Remote Similarity	0.6687	NPC477556
Remote Similarity	0.6626	NPC472103
Remote Similarity	0.6486	NPC101139
Remote Similarity	0.6424	NPC311330
Remote Similarity	0.6382	NPC477061
Remote Similarity	0.6382	NPC45777
Remote Similarity	0.6347	NPC472100
Remote Similarity	0.6299	NPC252878
Remote Similarity	0.6294	NPC88267
Remote Similarity	0.6294	NPC224610
Remote Similarity	0.6294	NPC194390
Remote Similarity	0.6294	NPC113326
Remote Similarity	0.6286	NPC85651
Remote Similarity	0.628	NPC243162
Remote Similarity	0.6273	NPC313352
Remote Similarity	0.6272	NPC475168
Remote Similarity	0.6272	NPC7817
Remote Similarity	0.6272	NPC321617
Remote Similarity	0.6258	NPC46427
Remote Similarity	0.6258	NPC287358
Remote Similarity	0.6258	NPC35996
Remote Similarity	0.6258	NPC283130
Remote Similarity	0.6258	NPC328683
Remote Similarity	0.6258	NPC477557
Remote Similarity	0.625	NPC32858
Remote Similarity	0.625	NPC264589
Remote Similarity	0.625	NPC194857
Remote Similarity	0.6199	NPC286551
Remote Similarity	0.619	NPC470824
Remote Similarity	0.6185	NPC203424
Remote Similarity	0.6185	NPC206372
Remote Similarity	0.6171	NPC471527
Remote Similarity	0.617	NPC46413
Remote Similarity	0.6169	NPC476990
Remote Similarity	0.6163	NPC470902
Remote Similarity	0.6162	NPC477159
Remote Similarity	0.6159	NPC218710
Remote Similarity	0.6149	NPC477156
Remote Similarity	0.6149	NPC477157
Remote Similarity	0.6145	NPC161069
Remote Similarity	0.6144	NPC237420
Remote Similarity	0.6144	NPC314992
Remote Similarity	0.6129	NPC202521
Remote Similarity	0.6118	NPC2265
Remote Similarity	0.6118	NPC254798
Remote Similarity	0.6118	NPC212799
Remote Similarity	0.6105	NPC122590
Remote Similarity	0.6102	NPC253667
Remote Similarity	0.6102	NPC471053
Remote Similarity	0.6102	NPC471052
Remote Similarity	0.6102	NPC35510
Remote Similarity	0.6102	NPC471051
Remote Similarity	0.6098	NPC127741
Remote Similarity	0.6087	NPC475094
Remote Similarity	0.6078	NPC254088
Remote Similarity	0.6078	NPC169328
Remote Similarity	0.6076	NPC325013
Remote Similarity	0.6071	NPC314287
Remote Similarity	0.6067	NPC292143
Remote Similarity	0.6067	NPC189116
Remote Similarity	0.6067	NPC139506
Remote Similarity	0.6058	NPC315403
Remote Similarity	0.6056	NPC469462
Remote Similarity	0.6051	NPC6975
Remote Similarity	0.6048	NPC316202
Remote Similarity	0.6045	NPC309531
Remote Similarity	0.6045	NPC472102
Remote Similarity	0.6039	NPC310467
Remote Similarity	0.6028	NPC25565
Remote Similarity	0.6026	NPC71684
Remote Similarity	0.6026	NPC1986
Remote Similarity	0.6026	NPC474544
Remote Similarity	0.6025	NPC226662
Remote Similarity	0.6013	NPC147957
Remote Similarity	0.6013	NPC470544
Remote Similarity	0.6012	NPC475763
Remote Similarity	0.6012	NPC314223
Remote Similarity	0.6011	NPC472121
Remote Similarity	0.6011	NPC189812
Remote Similarity	0.6011	NPC329688
Remote Similarity	0.6	NPC476950
Remote Similarity	0.6	NPC316405
Remote Similarity	0.6	NPC68865
Remote Similarity	0.6	NPC116519
Remote Similarity	0.6	NPC138775
Remote Similarity	0.6	NPC478140
Remote Similarity	0.5989	NPC472108
Remote Similarity	0.5989	NPC472110
Remote Similarity	0.5989	NPC139291
Remote Similarity	0.5989	NPC472109
Remote Similarity	0.5987	NPC205652
Remote Similarity	0.5987	NPC470550
Remote Similarity	0.5986	NPC473501
Remote Similarity	0.5986	NPC475439
Remote Similarity	0.5979	NPC291759
Remote Similarity	0.5978	NPC311276
Remote Similarity	0.5976	NPC315266
Remote Similarity	0.5976	NPC209509
Remote Similarity	0.5975	NPC474847
Remote Similarity	0.5975	NPC47667
Remote Similarity	0.5974	NPC470545
Remote Similarity	0.5966	NPC36836
Remote Similarity	0.5966	NPC63370
Remote Similarity	0.5965	NPC105717
Remote Similarity	0.5963	NPC259098
Remote Similarity	0.5963	NPC197680
Remote Similarity	0.5963	NPC40488
Remote Similarity	0.5959	NPC147000
Remote Similarity	0.5959	NPC150254
Remote Similarity	0.5959	NPC304761
Remote Similarity	0.5959	NPC226778
Remote Similarity	0.5957	NPC58674
Remote Similarity	0.5952	NPC212850
Remote Similarity	0.5952	NPC83289
Remote Similarity	0.5952	NPC189724
Remote Similarity	0.5951	NPC476685
Remote Similarity	0.5951	NPC476689
Remote Similarity	0.5951	NPC476687
Remote Similarity	0.5944	NPC472106
Remote Similarity	0.5944	NPC470069
Remote Similarity	0.5944	NPC52059
Remote Similarity	0.5941	NPC262077
Remote Similarity	0.5938	NPC477937
Remote Similarity	0.5935	NPC470546
Remote Similarity	0.5932	NPC153694
Remote Similarity	0.5932	NPC211525
Remote Similarity	0.5931	NPC291610
Remote Similarity	0.593	NPC2501
Remote Similarity	0.5928	NPC239762
Remote Similarity	0.5928	NPC163392
Remote Similarity	0.5926	NPC52262
Remote Similarity	0.5926	NPC133591
Remote Similarity	0.5926	NPC69496
Remote Similarity	0.5924	NPC477462
Remote Similarity	0.5917	NPC476978
Remote Similarity	0.5916	NPC284706
Remote Similarity	0.5914	NPC270009
Remote Similarity	0.5904	NPC159589
Remote Similarity	0.5904	NPC471264
Remote Similarity	0.5904	NPC472444
Remote Similarity	0.5904	NPC471265
Remote Similarity	0.5902	NPC83241
Remote Similarity	0.5901	NPC319766
Remote Similarity	0.5901	NPC478079
Remote Similarity	0.5899	NPC63210
Remote Similarity	0.5899	NPC310403
Remote Similarity	0.5899	NPC243673
Remote Similarity	0.5899	NPC148468
Remote Similarity	0.5899	NPC263709
Remote Similarity	0.5899	NPC97380
Remote Similarity	0.5892	NPC24594
Remote Similarity	0.5892	NPC472122
Remote Similarity	0.5889	NPC40779
Remote Similarity	0.5889	NPC474217
Remote Similarity	0.5886	NPC317474
Remote Similarity	0.5886	NPC169485
Remote Similarity	0.5886	NPC84281
Remote Similarity	0.5886	NPC291027
Remote Similarity	0.5886	NPC213126
Remote Similarity	0.5882	NPC11149
Remote Similarity	0.5882	NPC322878
Remote Similarity	0.5879	NPC311357
Remote Similarity	0.5876	NPC297145
Remote Similarity	0.5876	NPC197743
Remote Similarity	0.5875	NPC474479
Remote Similarity	0.5874	NPC311242
Remote Similarity	0.5872	NPC471820
Remote Similarity	0.5872	NPC471821
Remote Similarity	0.587	NPC34508
Remote Similarity	0.5868	NPC77992
Remote Similarity	0.5867	NPC65855
Remote Similarity	0.5867	NPC292758
Remote Similarity	0.5866	NPC477158
Remote Similarity	0.5866	NPC68650
Remote Similarity	0.5866	NPC320064
Remote Similarity	0.5866	NPC73655
Remote Similarity	0.5864	NPC328590
Remote Similarity	0.5862	NPC214200
Remote Similarity	0.5862	NPC228400
Remote Similarity	0.586	NPC478016
Remote Similarity	0.586	NPC478015
Remote Similarity	0.586	NPC190663
Remote Similarity	0.586	NPC478014
Remote Similarity	0.5858	NPC314113
Remote Similarity	0.5858	NPC168861
Remote Similarity	0.5855	NPC474584
Remote Similarity	0.5845	NPC303045
Remote Similarity	0.5845	NPC161972
Remote Similarity	0.5843	NPC469762
Remote Similarity	0.5842	NPC62510
Remote Similarity	0.5838	NPC472586
Remote Similarity	0.5838	NPC95412
Remote Similarity	0.5838	NPC475097
Remote Similarity	0.5838	NPC245974
Remote Similarity	0.5833	NPC46098
Remote Similarity	0.5833	NPC472120
Remote Similarity	0.5833	NPC472101
Remote Similarity	0.5833	NPC191863
Remote Similarity	0.5833	NPC268841

Drug Structure

NPD6378 OpenBabel08211709092D 39 41 0 0 1 0 0 0 0 0999 V2000 -1.7321 3.0000 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 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 -2.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 5.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 5.7024 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 -0.8660 1.5000 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 5.2437 4.0933 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 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 1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 4.8364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 0.8660 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 -0.8660 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 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 33 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 33 1 0 0 0 0 20 26 1 0 0 0 0 21 34 1 1 0 0 0 22 35 1 0 0 0 0 23 14 1 1 0 0 0 23 24 1 0 0 0 0 23 27 1 0 0 0 0 24 16 1 6 0 0 0 24 29 1 0 0 0 0 25 27 2 3 0 0 0 25 30 1 0 0 0 0 25 34 1 0 0 0 0 26 36 1 0 0 0 0 26 37 1 0 0 0 0 28 35 1 0 0 0 0 29 38 1 0 0 0 0 30 39 1 0 0 0 0 31 35 2 0 0 0 0 32 35 2 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000170
DrugBank	DB00701
ChEMBL	CHEMBL116
IUPHAR/BPS
PharmaGKB	PA448422
KEGG Drug	D00894
PubChem CID	65016
ChEBI	40050
CAS Number	161814-49-9

Drug Properties

Molecular Weight	505.22
ALogP	-1.7012
MLogP	3.11
XLogP	4.76
HDA	9
HBD	3
Rotatable Bonds	17
TPSA	143.06
RO5 Violation	1