NPASS drugs

Drug Information

Drug ID:	NPD1948
Drug Name:	Fosphenytoin
Molecular Formula:	C16H15N2O6P
Canonical SMILES:	O=C1N(COP(=O)(O)O)C(=NC1(c1ccccc1)c1ccccc1)O
Standard InCHI:	InChI=1S/C16H15N2O6P/c19-14-16(12-7-3-1-4-8-12,13-9-5-2-6-10-13)17-15(20)18(14)11-24-25(21,22)23/h1-10H,11H2,(H,17,20)(H2,21,22,23)
Standard InCHIKey:	XWLUWCNOOVRFPX-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD1948

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	98
0.1-0.2	1125
0.2-0.3	6265
0.3-0.4	13945
0.4-0.5	8275
0.5-0.6	1098
0.6-0.7	83
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	0.7016	NPC473418
Remote Similarity	0.6842	NPC220698
Remote Similarity	0.6825	NPC45033
Remote Similarity	0.6767	NPC470545
Remote Similarity	0.6716	NPC470546
Remote Similarity	0.6692	NPC285926
Remote Similarity	0.6692	NPC470544
Remote Similarity	0.6692	NPC315276
Remote Similarity	0.6692	NPC14672
Remote Similarity	0.669	NPC132636
Remote Similarity	0.6618	NPC200964
Remote Similarity	0.6618	NPC27833
Remote Similarity	0.6596	NPC473322
Remote Similarity	0.6573	NPC32858
Remote Similarity	0.6573	NPC194857
Remote Similarity	0.6557	NPC108339
Remote Similarity	0.6549	NPC200589
Remote Similarity	0.6508	NPC329375
Remote Similarity	0.6503	NPC255447
Remote Similarity	0.6479	NPC111428
Remote Similarity	0.6475	NPC474082
Remote Similarity	0.6475	NPC71140
Remote Similarity	0.6475	NPC175726
Remote Similarity	0.6454	NPC477937
Remote Similarity	0.6449	NPC71684
Remote Similarity	0.6423	NPC256452
Remote Similarity	0.6418	NPC33742
Remote Similarity	0.6385	NPC55529
Remote Similarity	0.6383	NPC101719
Remote Similarity	0.6377	NPC302169
Remote Similarity	0.6371	NPC471320
Remote Similarity	0.6371	NPC471319
Remote Similarity	0.6357	NPC6975
Remote Similarity	0.6343	NPC35850
Remote Similarity	0.6343	NPC276949
Remote Similarity	0.6333	NPC161069
Remote Similarity	0.6327	NPC300299
Remote Similarity	0.6324	NPC239357
Remote Similarity	0.6312	NPC222466
Remote Similarity	0.6308	NPC471447
Remote Similarity	0.6279	NPC469974
Remote Similarity	0.6268	NPC79698
Remote Similarity	0.6241	NPC319579
Remote Similarity	0.6233	NPC325479
Remote Similarity	0.6233	NPC207428
Remote Similarity	0.6231	NPC167336
Remote Similarity	0.6231	NPC476198
Remote Similarity	0.6214	NPC202521
Remote Similarity	0.6202	NPC471317
Remote Similarity	0.6183	NPC473498
Remote Similarity	0.6169	NPC138775
Remote Similarity	0.6164	NPC120251
Remote Similarity	0.6159	NPC207554
Remote Similarity	0.6149	NPC248283
Remote Similarity	0.6144	NPC209509
Remote Similarity	0.6143	NPC476990
Remote Similarity	0.6131	NPC473573
Remote Similarity	0.6129	NPC324445
Remote Similarity	0.6122	NPC257390
Remote Similarity	0.6122	NPC473962
Remote Similarity	0.6107	NPC473360
Remote Similarity	0.6104	NPC314114
Remote Similarity	0.6104	NPC262077
Remote Similarity	0.6094	NPC12730
Remote Similarity	0.608	NPC7067
Remote Similarity	0.6077	NPC164859
Remote Similarity	0.6071	NPC226143
Remote Similarity	0.6063	NPC472258
Remote Similarity	0.6056	NPC252878
Remote Similarity	0.6054	NPC126458
Remote Similarity	0.6054	NPC130309
Remote Similarity	0.6053	NPC269398
Remote Similarity	0.6053	NPC263493
Remote Similarity	0.6027	NPC469666
Remote Similarity	0.6026	NPC92784
Remote Similarity	0.6026	NPC476133
Remote Similarity	0.6026	NPC178662
Remote Similarity	0.6026	NPC470884
Remote Similarity	0.6026	NPC98424
Remote Similarity	0.6016	NPC322598
Remote Similarity	0.6014	NPC46427
Remote Similarity	0.6014	NPC288232
Remote Similarity	0.6014	NPC188010
Remote Similarity	0.6	NPC136453
Remote Similarity	0.5988	NPC104345
Remote Similarity	0.5987	NPC83214
Remote Similarity	0.5986	NPC179224
Remote Similarity	0.5985	NPC143516
Remote Similarity	0.5975	NPC122590
Remote Similarity	0.5974	NPC476978
Remote Similarity	0.5972	NPC22746
Remote Similarity	0.5962	NPC16188
Remote Similarity	0.596	NPC127741
Remote Similarity	0.5959	NPC152850
Remote Similarity	0.5959	NPC105114
Remote Similarity	0.5959	NPC239990
Remote Similarity	0.5959	NPC319766
Remote Similarity	0.5959	NPC89923
Remote Similarity	0.5959	NPC71933
Remote Similarity	0.5954	NPC202613
Remote Similarity	0.5952	NPC322040
Remote Similarity	0.5951	NPC154478
Remote Similarity	0.5951	NPC469243
Remote Similarity	0.594	NPC191215
Remote Similarity	0.594	NPC130898
Remote Similarity	0.594	NPC474973
Remote Similarity	0.594	NPC274089
Remote Similarity	0.594	NPC474804
Remote Similarity	0.5935	NPC471680
Remote Similarity	0.5935	NPC5620
Remote Similarity	0.5933	NPC474473
Remote Similarity	0.5932	NPC471195
Remote Similarity	0.5932	NPC471196
Remote Similarity	0.5931	NPC474926
Remote Similarity	0.5926	NPC84317
Remote Similarity	0.5926	NPC324850
Remote Similarity	0.5924	NPC105717
Remote Similarity	0.5921	NPC89489
Remote Similarity	0.592	NPC470926
Remote Similarity	0.5918	NPC150863
Remote Similarity	0.5918	NPC165726
Remote Similarity	0.5918	NPC313722
Remote Similarity	0.5918	NPC213969
Remote Similarity	0.5912	NPC474584
Remote Similarity	0.5909	NPC139326
Remote Similarity	0.5909	NPC470301
Remote Similarity	0.5906	NPC246913
Remote Similarity	0.5903	NPC35996
Remote Similarity	0.5902	NPC203076
Remote Similarity	0.5894	NPC118099
Remote Similarity	0.5894	NPC474811
Remote Similarity	0.5894	NPC151706
Remote Similarity	0.5894	NPC273907
Remote Similarity	0.5894	NPC293377
Remote Similarity	0.5894	NPC90194
Remote Similarity	0.5894	NPC9687
Remote Similarity	0.5894	NPC474855
Remote Similarity	0.5894	NPC76785
Remote Similarity	0.5894	NPC260045
Remote Similarity	0.5894	NPC475598
Remote Similarity	0.5894	NPC79465
Remote Similarity	0.5894	NPC475318
Remote Similarity	0.5894	NPC49577
Remote Similarity	0.5894	NPC474787
Remote Similarity	0.5894	NPC314835
Remote Similarity	0.5894	NPC476102
Remote Similarity	0.5887	NPC310467
Remote Similarity	0.5886	NPC283783
Remote Similarity	0.5886	NPC254798
Remote Similarity	0.5882	NPC307357
Remote Similarity	0.5882	NPC46098
Remote Similarity	0.5882	NPC469560
Remote Similarity	0.5882	NPC268841
Remote Similarity	0.5878	NPC300315
Remote Similarity	0.5875	NPC66936
Remote Similarity	0.5871	NPC52748
Remote Similarity	0.5867	NPC287401
Remote Similarity	0.5865	NPC67043
Remote Similarity	0.586	NPC311658
Remote Similarity	0.5855	NPC471265
Remote Similarity	0.5855	NPC471264
Remote Similarity	0.5854	NPC305602
Remote Similarity	0.5854	NPC475544
Remote Similarity	0.5854	NPC17497
Remote Similarity	0.5854	NPC473031
Remote Similarity	0.5852	NPC473676
Remote Similarity	0.5847	NPC272260
Remote Similarity	0.5844	NPC315051
Remote Similarity	0.5844	NPC150712
Remote Similarity	0.5843	NPC223207
Remote Similarity	0.5843	NPC113056
Remote Similarity	0.5843	NPC138293
Remote Similarity	0.584	NPC316108
Remote Similarity	0.5839	NPC157311
Remote Similarity	0.5839	NPC329011
Remote Similarity	0.5839	NPC183722
Remote Similarity	0.5839	NPC473002
Remote Similarity	0.5839	NPC181390
Remote Similarity	0.5833	NPC317474
Remote Similarity	0.5833	NPC213126
Remote Similarity	0.5833	NPC169485
Remote Similarity	0.5833	NPC291027
Remote Similarity	0.5833	NPC84281
Remote Similarity	0.5828	NPC141050
Remote Similarity	0.5823	NPC9373
Remote Similarity	0.5822	NPC47667
Remote Similarity	0.5822	NPC4974
Remote Similarity	0.5817	NPC313694
Remote Similarity	0.5817	NPC242159
Remote Similarity	0.5816	NPC169328
Remote Similarity	0.5814	NPC311242
Remote Similarity	0.5814	NPC122493
Remote Similarity	0.5814	NPC10781
Remote Similarity	0.5814	NPC293628
Remote Similarity	0.5813	NPC233702
Remote Similarity	0.5812	NPC9796
Remote Similarity	0.5811	NPC472413
Remote Similarity	0.5809	NPC158854
Remote Similarity	0.5808	NPC471771
Remote Similarity	0.5808	NPC304074

Drug Structure

NPD1948 OpenBabel08211701392D 28 30 0 0 0 0 0 0 0 0999 V2000 7.7583 -1.7266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0894 -3.9742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1895 -2.5095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3647 -0.8425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6582 -3.1913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1270 -3.8730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2271 -2.4083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4023 -0.7414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2646 -2.3072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7333 -2.9890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4516 -0.8381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8334 -1.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3022 -2.2060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9882 -1.6210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9882 -0.0552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9086 -1.3220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9086 -0.3542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.4194 -0.8381 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.6891 -2.5414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6891 0.8652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9677 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9677 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9677 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9677 -0.0000 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 1.7425 1.0664 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8381 -1.4516 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4516 0.8381 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 4 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 12 2 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 10 13 1 0 0 0 0 11 18 1 0 0 0 0 11 24 1 0 0 0 0 12 16 1 0 0 0 0 13 16 1 0 0 0 0 14 16 1 0 0 0 0 14 18 1 0 0 0 0 14 19 2 0 0 0 0 15 17 2 0 0 0 0 15 18 1 0 0 0 0 15 20 1 0 0 0 0 16 17 1 0 0 0 0 20 26 1 0 0 0 0 21 25 1 0 0 0 0 21 27 1 0 0 0 0 22 25 1 0 0 0 0 22 28 1 0 0 0 0 23 25 2 0 0 0 0 24 25 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000520
DrugBank	DB01320
ChEMBL	CHEMBL1201336
IUPHAR/BPS	7190
PharmaGKB	PA164746820
KEGG Drug
PubChem CID	56339
ChEBI	5165
CAS Number	93390-81-9

Drug Properties

Molecular Weight	362.07
ALogP	-0.8735
MLogP	2.23
XLogP	3.213
HDA	8
HBD	3
Rotatable Bonds	8
TPSA	129.47
RO5 Violation	0