NPASS drugs

Drug Information

Drug ID:	NPD5219
Drug Name:	Sofosbuvir
Molecular Formula:	C22H29FN3O9P
Canonical SMILES:	CC(OC(=O)[C@@H](N[P@@](=O)(Oc1ccccc1)OC[C@H]1O[C@H]([C@]([C@@H]1O)(C)F)n1ccc(nc1=O)O)C)C
Standard InCHI:	InChI=1S/C22H29FN3O9P/c1-13(2)33-19(29)14(3)25-36(31,35-15-8-6-5-7-9-15)32-12-16-18(28)22(4,23)20(34-16)26-11-10-17(27)24-21(26)30/h5-11,13-14,16,18,20,28H,12H2,1-4H3,(H,25,31)(H,24,27,30)/t14-,16+,18+,20+,22+,36-/m0/s1
Standard InCHIKey:	TTZHDVOVKQGIBA-IQWMDFIBSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD5219

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	124
0.1-0.2	883
0.2-0.3	5222
0.3-0.4	8231
0.4-0.5	13834
0.5-0.6	2350
0.6-0.7	244
0.7-0.8	2
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	0.7135	NPC471165
Intermediate Similarity	0.7079	NPC248670
Remote Similarity	0.699	NPC478005
Remote Similarity	0.6966	NPC46009
Remote Similarity	0.6966	NPC475204
Remote Similarity	0.6966	NPC475123
Remote Similarity	0.694	NPC473404
Remote Similarity	0.6889	NPC273755
Remote Similarity	0.6851	NPC26108
Remote Similarity	0.6845	NPC94862
Remote Similarity	0.6833	NPC89831
Remote Similarity	0.6831	NPC269750
Remote Similarity	0.6831	NPC194671
Remote Similarity	0.6813	NPC50016
Remote Similarity	0.6809	NPC102959
Remote Similarity	0.6807	NPC197921
Remote Similarity	0.6804	NPC476661
Remote Similarity	0.6772	NPC60516
Remote Similarity	0.6769	NPC476662
Remote Similarity	0.6766	NPC469360
Remote Similarity	0.6766	NPC91953
Remote Similarity	0.6742	NPC63931
Remote Similarity	0.6739	NPC45037
Remote Similarity	0.6724	NPC476268
Remote Similarity	0.6722	NPC280022
Remote Similarity	0.6703	NPC306804
Remote Similarity	0.6701	NPC477550
Remote Similarity	0.6701	NPC477552
Remote Similarity	0.6699	NPC478007
Remote Similarity	0.6686	NPC7817
Remote Similarity	0.6686	NPC475168
Remote Similarity	0.6684	NPC61332
Remote Similarity	0.6684	NPC471050
Remote Similarity	0.6684	NPC471048
Remote Similarity	0.6684	NPC240130
Remote Similarity	0.6684	NPC471049
Remote Similarity	0.6667	NPC294516
Remote Similarity	0.6667	NPC158277
Remote Similarity	0.6667	NPC302715
Remote Similarity	0.6667	NPC279871
Remote Similarity	0.6667	NPC107938
Remote Similarity	0.6667	NPC473354
Remote Similarity	0.6667	NPC470902
Remote Similarity	0.6635	NPC478008
Remote Similarity	0.6633	NPC477551
Remote Similarity	0.6629	NPC244509
Remote Similarity	0.6627	NPC6570
Remote Similarity	0.6613	NPC475564
Remote Similarity	0.6613	NPC475409
Remote Similarity	0.6613	NPC170302
Remote Similarity	0.6612	NPC137627
Remote Similarity	0.661	NPC244336
Remote Similarity	0.6596	NPC294951
Remote Similarity	0.6593	NPC40234
Remote Similarity	0.6588	NPC266741
Remote Similarity	0.6588	NPC244536
Remote Similarity	0.6576	NPC476227
Remote Similarity	0.6557	NPC230611
Remote Similarity	0.6557	NPC328494
Remote Similarity	0.655	NPC81026
Remote Similarity	0.6546	NPC477632
Remote Similarity	0.6546	NPC477638
Remote Similarity	0.6531	NPC323662
Remote Similarity	0.6519	NPC61004
Remote Similarity	0.6519	NPC254700
Remote Similarity	0.6505	NPC473546
Remote Similarity	0.6495	NPC328763
Remote Similarity	0.6495	NPC314083
Remote Similarity	0.6494	NPC473491
Remote Similarity	0.6489	NPC476321
Remote Similarity	0.6489	NPC477637
Remote Similarity	0.6486	NPC155506
Remote Similarity	0.6486	NPC473402
Remote Similarity	0.6486	NPC159767
Remote Similarity	0.6484	NPC209463
Remote Similarity	0.6477	NPC476742
Remote Similarity	0.6471	NPC119652
Remote Similarity	0.6471	NPC97526
Remote Similarity	0.6465	NPC469443
Remote Similarity	0.6461	NPC326349
Remote Similarity	0.6461	NPC323336
Remote Similarity	0.6455	NPC471526
Remote Similarity	0.645	NPC48202
Remote Similarity	0.6443	NPC477631
Remote Similarity	0.6441	NPC476741
Remote Similarity	0.6433	NPC204546
Remote Similarity	0.6425	NPC163961
Remote Similarity	0.6425	NPC477636
Remote Similarity	0.6425	NPC473305
Remote Similarity	0.642	NPC473341
Remote Similarity	0.64	NPC476743
Remote Similarity	0.6398	NPC477462
Remote Similarity	0.6389	NPC114806
Remote Similarity	0.6374	NPC168861
Remote Similarity	0.6364	NPC476744
Remote Similarity	0.6353	NPC214988
Remote Similarity	0.6335	NPC474862
Remote Similarity	0.6333	NPC24617
Remote Similarity	0.6333	NPC1390
Remote Similarity	0.6333	NPC62104
Remote Similarity	0.6331	NPC64205
Remote Similarity	0.6328	NPC262166
Remote Similarity	0.6328	NPC56685
Remote Similarity	0.6324	NPC274198
Remote Similarity	0.6324	NPC196091
Remote Similarity	0.6324	NPC198254
Remote Similarity	0.6324	NPC276506
Remote Similarity	0.6322	NPC311658
Remote Similarity	0.6321	NPC96275
Remote Similarity	0.631	NPC17698
Remote Similarity	0.6304	NPC328649
Remote Similarity	0.6302	NPC299806
Remote Similarity	0.6294	NPC313694
Remote Similarity	0.6294	NPC242159
Remote Similarity	0.6292	NPC39431
Remote Similarity	0.6287	NPC45191
Remote Similarity	0.6287	NPC326966
Remote Similarity	0.6286	NPC471821
Remote Similarity	0.6286	NPC471820
Remote Similarity	0.6284	NPC472923
Remote Similarity	0.6275	NPC220060
Remote Similarity	0.6271	NPC162104
Remote Similarity	0.627	NPC129486
Remote Similarity	0.6265	NPC325651
Remote Similarity	0.6263	NPC477639
Remote Similarity	0.6257	NPC475532
Remote Similarity	0.6257	NPC473580
Remote Similarity	0.6256	NPC51047
Remote Similarity	0.625	NPC2501
Remote Similarity	0.6244	NPC469444
Remote Similarity	0.6243	NPC52748
Remote Similarity	0.6237	NPC471568
Remote Similarity	0.6237	NPC473693
Remote Similarity	0.6236	NPC122590
Remote Similarity	0.6232	NPC326333
Remote Similarity	0.6224	NPC473378
Remote Similarity	0.6224	NPC473407
Remote Similarity	0.6224	NPC248822
Remote Similarity	0.6223	NPC165285
Remote Similarity	0.6221	NPC476989
Remote Similarity	0.6218	NPC315542
Remote Similarity	0.6209	NPC475544
Remote Similarity	0.6209	NPC469243
Remote Similarity	0.6205	NPC296712
Remote Similarity	0.6196	NPC217804
Remote Similarity	0.6196	NPC22883
Remote Similarity	0.6196	NPC210377
Remote Similarity	0.6196	NPC5719
Remote Similarity	0.6195	NPC194699
Remote Similarity	0.6195	NPC219350
Remote Similarity	0.619	NPC196243
Remote Similarity	0.6188	NPC197743
Remote Similarity	0.6188	NPC297145
Remote Similarity	0.6183	NPC186617
Remote Similarity	0.6181	NPC329295
Remote Similarity	0.618	NPC300443
Remote Similarity	0.6173	NPC326079
Remote Similarity	0.6172	NPC326027
Remote Similarity	0.6167	NPC123011
Remote Similarity	0.6167	NPC256689
Remote Similarity	0.6162	NPC65714
Remote Similarity	0.6158	NPC132771
Remote Similarity	0.6154	NPC469445
Remote Similarity	0.6154	NPC274732
Remote Similarity	0.6154	NPC471953
Remote Similarity	0.6141	NPC471053
Remote Similarity	0.6141	NPC471052
Remote Similarity	0.6141	NPC471051
Remote Similarity	0.614	NPC127741
Remote Similarity	0.6139	NPC473450
Remote Similarity	0.6136	NPC119569
Remote Similarity	0.6136	NPC16188
Remote Similarity	0.6135	NPC27581
Remote Similarity	0.6129	NPC63040
Remote Similarity	0.6129	NPC302597
Remote Similarity	0.6126	NPC475421
Remote Similarity	0.6122	NPC246591
Remote Similarity	0.612	NPC471527
Remote Similarity	0.6118	NPC267237
Remote Similarity	0.6114	NPC106183
Remote Similarity	0.6114	NPC315266
Remote Similarity	0.6111	NPC476183
Remote Similarity	0.6108	NPC472329
Remote Similarity	0.6108	NPC472330
Remote Similarity	0.6108	NPC223207
Remote Similarity	0.6105	NPC77992
Remote Similarity	0.6102	NPC9373
Remote Similarity	0.6102	NPC313414
Remote Similarity	0.61	NPC473371
Remote Similarity	0.6099	NPC212699
Remote Similarity	0.6099	NPC207675
Remote Similarity	0.6099	NPC56635
Remote Similarity	0.6096	NPC315388
Remote Similarity	0.6094	NPC153554
Remote Similarity	0.6092	NPC212850
Remote Similarity	0.6092	NPC189724
Remote Similarity	0.6092	NPC83289
Remote Similarity	0.6087	NPC241794
Remote Similarity	0.6084	NPC65310
Remote Similarity	0.608	NPC314358

Drug Structure

NPD5219 OpenBabel08211706322D 39 41 0 0 1 0 0 0 0 0999 V2000 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 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 5.0334 1.4706 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 -2.5981 -1.5000 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 -1.7321 -1.0000 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 5.5523 -1.8041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7433 -1.2163 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 0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 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 2.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4659 -1.3973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 1.6750 0.0000 C 0 0 2 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 4.0388 0.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7614 0.1850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0388 1.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4456 2.2796 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 6.5704 -0.4028 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 4.8479 -0.2218 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.2749 -1.9851 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7788 2.6261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8659 1.1795 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 1.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 0.0570 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 2 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 7.1704 -2.9796 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4479 3.3692 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 15 2 0 0 0 0 9 15 1 0 0 0 0 10 11 2 0 0 0 0 10 17 1 0 0 0 0 11 26 1 0 0 0 0 12 32 1 0 0 0 0 13 33 1 0 0 0 0 14 3 1 1 0 0 0 14 19 1 0 0 0 0 14 25 1 0 0 0 0 15 35 1 0 0 0 0 16 12 1 6 0 0 0 16 18 1 0 0 0 0 16 34 1 0 0 0 0 17 24 2 0 0 0 0 17 27 1 0 0 0 0 18 22 1 1 0 0 0 18 28 1 0 0 0 0 19 29 2 0 0 0 0 19 33 1 0 0 0 0 20 22 1 6 0 0 0 20 26 1 0 0 0 0 20 34 1 0 0 0 0 21 24 1 0 0 0 0 21 26 1 0 0 0 0 21 30 2 0 0 0 0 22 4 1 6 0 0 0 22 23 1 0 0 0 0 25 36 1 0 0 0 0 25 37 1 0 0 0 0 27 38 1 0 0 0 0 28 39 1 0 0 0 0 32 36 1 0 0 0 0 35 36 1 0 0 0 0 36 31 2 1 0 0 0 M END $$$$

External Identifiers

TTD	DNAP001709; DCL001224
DrugBank
ChEMBL
IUPHAR/BPS	7368
PharmaGKB
KEGG Drug
PubChem CID	45375808
ChEBI
CAS Number

Drug Properties

Molecular Weight	529.16
ALogP	-1.7283
MLogP	2.34
XLogP	2.197
HDA	11
HBD	3
Rotatable Bonds	18
TPSA	166.03
RO5 Violation	2