NPASS drugs

Drug Information

Drug ID:	NPD2016
Drug Name:	Cephalexin
Molecular Formula:	C16H17N3O4S
Canonical SMILES:	N[C@@H](C(=N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)C)O)c1ccccc1
Standard InCHI:	InChI=1S/C16H17N3O4S/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,15-/m1/s1
Standard InCHIKey:	ZAIPMKNFIOOWCQ-UEKVPHQBSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD2016

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	107
0.1-0.2	1132
0.2-0.3	6036
0.3-0.4	12402
0.4-0.5	9236
0.5-0.6	1581
0.6-0.7	381
0.7-0.8	12
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
0.95-1	1

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
High Similarity	1.0	NPC13470
High Similarity	0.9013	NPC315388
High Similarity	0.9007	NPC468984
Intermediate Similarity	0.7419	NPC471680
Intermediate Similarity	0.7333	NPC189116
Intermediate Similarity	0.7315	NPC300315
Intermediate Similarity	0.7241	NPC71684
Intermediate Similarity	0.7211	NPC22746
Intermediate Similarity	0.7208	NPC77992
Intermediate Similarity	0.7197	NPC322878
Intermediate Similarity	0.717	NPC105717
Intermediate Similarity	0.7133	NPC470544
Intermediate Similarity	0.7083	NPC470545
Intermediate Similarity	0.7034	NPC470546
Intermediate Similarity	0.7014	NPC239357
Remote Similarity	0.6994	NPC286551
Remote Similarity	0.6993	NPC33742
Remote Similarity	0.6987	NPC89489
Remote Similarity	0.6987	NPC132636
Remote Similarity	0.6971	NPC153554
Remote Similarity	0.6952	NPC143325
Remote Similarity	0.6933	NPC101719
Remote Similarity	0.6918	NPC220698
Remote Similarity	0.6914	NPC254798
Remote Similarity	0.6908	NPC469666
Remote Similarity	0.6894	NPC83790
Remote Similarity	0.6894	NPC128237
Remote Similarity	0.6894	NPC311658
Remote Similarity	0.6883	NPC246079
Remote Similarity	0.6871	NPC475168
Remote Similarity	0.6871	NPC7817
Remote Similarity	0.6867	NPC222466
Remote Similarity	0.6826	NPC326349
Remote Similarity	0.6826	NPC323336
Remote Similarity	0.6815	NPC127741
Remote Similarity	0.6807	NPC469903
Remote Similarity	0.6797	NPC111428
Remote Similarity	0.6795	NPC474473
Remote Similarity	0.6788	NPC473341
Remote Similarity	0.6781	NPC14672
Remote Similarity	0.6781	NPC315276
Remote Similarity	0.6781	NPC285926
Remote Similarity	0.6779	NPC202521
Remote Similarity	0.6774	NPC325479
Remote Similarity	0.677	NPC266741
Remote Similarity	0.6747	NPC470902
Remote Similarity	0.6746	NPC469243
Remote Similarity	0.6743	NPC317725
Remote Similarity	0.6743	NPC326407
Remote Similarity	0.6743	NPC318930
Remote Similarity	0.6743	NPC317362
Remote Similarity	0.6728	NPC81026
Remote Similarity	0.6711	NPC476990
Remote Similarity	0.6711	NPC474479
Remote Similarity	0.6708	NPC315283
Remote Similarity	0.6708	NPC314388
Remote Similarity	0.6707	NPC473580
Remote Similarity	0.669	NPC35850
Remote Similarity	0.669	NPC276949
Remote Similarity	0.6689	NPC6975
Remote Similarity	0.6688	NPC473322
Remote Similarity	0.6687	NPC135121
Remote Similarity	0.6667	NPC315266
Remote Similarity	0.6667	NPC477217
Remote Similarity	0.6667	NPC242159
Remote Similarity	0.6667	NPC313694
Remote Similarity	0.6667	NPC201244
Remote Similarity	0.6667	NPC327481
Remote Similarity	0.6667	NPC313867
Remote Similarity	0.6667	NPC316008
Remote Similarity	0.6647	NPC475544
Remote Similarity	0.6647	NPC469902
Remote Similarity	0.6628	NPC223207
Remote Similarity	0.6626	NPC314358
Remote Similarity	0.6625	NPC163392
Remote Similarity	0.6625	NPC476259
Remote Similarity	0.6625	NPC239762
Remote Similarity	0.6623	NPC319766
Remote Similarity	0.6623	NPC252878
Remote Similarity	0.6621	NPC474584
Remote Similarity	0.6606	NPC283783
Remote Similarity	0.6604	NPC68865
Remote Similarity	0.6604	NPC471264
Remote Similarity	0.6604	NPC471265
Remote Similarity	0.66	NPC302169
Remote Similarity	0.66	NPC200964
Remote Similarity	0.6597	NPC319579
Remote Similarity	0.6591	NPC248670
Remote Similarity	0.659	NPC304074
Remote Similarity	0.659	NPC471771
Remote Similarity	0.659	NPC61004
Remote Similarity	0.659	NPC290755
Remote Similarity	0.6584	NPC476989
Remote Similarity	0.6584	NPC263493
Remote Similarity	0.6584	NPC168113
Remote Similarity	0.6584	NPC269398
Remote Similarity	0.6579	NPC46427
Remote Similarity	0.6564	NPC209509
Remote Similarity	0.6558	NPC477937
Remote Similarity	0.6552	NPC329011
Remote Similarity	0.655	NPC114806
Remote Similarity	0.6548	NPC39431
Remote Similarity	0.6543	NPC161069
Remote Similarity	0.6543	NPC139326
Remote Similarity	0.6543	NPC176226
Remote Similarity	0.6543	NPC197682
Remote Similarity	0.6541	NPC477526
Remote Similarity	0.6532	NPC63931
Remote Similarity	0.6497	NPC255447
Remote Similarity	0.6497	NPC130309
Remote Similarity	0.6491	NPC24617
Remote Similarity	0.6486	NPC329961
Remote Similarity	0.6486	NPC122427
Remote Similarity	0.6486	NPC197470
Remote Similarity	0.6485	NPC16188
Remote Similarity	0.6481	NPC469427
Remote Similarity	0.6481	NPC469426
Remote Similarity	0.6477	NPC274198
Remote Similarity	0.6477	NPC46009
Remote Similarity	0.6477	NPC198254
Remote Similarity	0.6474	NPC133470
Remote Similarity	0.6474	NPC191863
Remote Similarity	0.6474	NPC289776
Remote Similarity	0.6471	NPC474082
Remote Similarity	0.6471	NPC175726
Remote Similarity	0.6467	NPC324081
Remote Similarity	0.6467	NPC329731
Remote Similarity	0.646	NPC476133
Remote Similarity	0.646	NPC470884
Remote Similarity	0.646	NPC98424
Remote Similarity	0.646	NPC178662
Remote Similarity	0.646	NPC92784
Remote Similarity	0.6456	NPC326966
Remote Similarity	0.6454	NPC164859
Remote Similarity	0.6438	NPC475013
Remote Similarity	0.6433	NPC325651
Remote Similarity	0.6429	NPC233702
Remote Similarity	0.6424	NPC473804
Remote Similarity	0.642	NPC469904
Remote Similarity	0.6416	NPC68650
Remote Similarity	0.6407	NPC2501
Remote Similarity	0.6402	NPC52748
Remote Similarity	0.6391	NPC122590
Remote Similarity	0.6391	NPC56685
Remote Similarity	0.6389	NPC14849
Remote Similarity	0.6387	NPC4974
Remote Similarity	0.6386	NPC145113
Remote Similarity	0.6386	NPC119569
Remote Similarity	0.6386	NPC225648
Remote Similarity	0.6386	NPC329761
Remote Similarity	0.6386	NPC138775
Remote Similarity	0.6384	NPC475123
Remote Similarity	0.6384	NPC475204
Remote Similarity	0.6384	NPC276506
Remote Similarity	0.6379	NPC471052
Remote Similarity	0.6379	NPC471051
Remote Similarity	0.6379	NPC471053
Remote Similarity	0.6378	NPC4910
Remote Similarity	0.6378	NPC478005
Remote Similarity	0.6375	NPC141050
Remote Similarity	0.6374	NPC477637
Remote Similarity	0.6369	NPC473491
Remote Similarity	0.6369	NPC158277
Remote Similarity	0.6364	NPC476198
Remote Similarity	0.6364	NPC5620
Remote Similarity	0.6364	NPC67043
Remote Similarity	0.6358	NPC477557
Remote Similarity	0.6358	NPC287358
Remote Similarity	0.6358	NPC154478
Remote Similarity	0.6358	NPC471527
Remote Similarity	0.6358	NPC314992
Remote Similarity	0.6358	NPC473003
Remote Similarity	0.6358	NPC469901
Remote Similarity	0.6354	NPC269750
Remote Similarity	0.6354	NPC194671
Remote Similarity	0.6353	NPC473002
Remote Similarity	0.6352	NPC257390
Remote Similarity	0.6351	NPC476048
Remote Similarity	0.6349	NPC184933
Remote Similarity	0.6349	NPC59827
Remote Similarity	0.6347	NPC9373
Remote Similarity	0.6337	NPC84317
Remote Similarity	0.6333	NPC2265
Remote Similarity	0.6333	NPC196243
Remote Similarity	0.6331	NPC300443
Remote Similarity	0.633	NPC165538
Remote Similarity	0.6329	NPC200589
Remote Similarity	0.6328	NPC129486
Remote Similarity	0.6328	NPC473000
Remote Similarity	0.6316	NPC244509
Remote Similarity	0.6316	NPC476268
Remote Similarity	0.6313	NPC273755
Remote Similarity	0.6313	NPC475532
Remote Similarity	0.6313	NPC306804
Remote Similarity	0.6312	NPC287401
Remote Similarity	0.6304	NPC161972
Remote Similarity	0.6304	NPC303045
Remote Similarity	0.6303	NPC476978
Remote Similarity	0.6301	NPC1390
Remote Similarity	0.6301	NPC469898

Drug Structure

NPD2016 OpenBabel08211701392D 28 30 0 0 1 0 0 0 0 0999 V2000 -3.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2779 -1.3789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0191 -2.3449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5708 -0.6718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0532 -2.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6049 -0.9306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3461 -1.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3801 -2.1554 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6730 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1213 -3.1213 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 -1.7071 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9319 -0.4824 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 0.7071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -1.5000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 2.8284 -3.8284 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1554 -3.3801 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8978 -0.2235 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1340 1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 9 2 0 0 0 0 6 9 1 0 0 0 0 7 8 1 0 0 0 0 7 24 1 0 0 0 0 8 12 2 0 0 0 0 9 10 1 0 0 0 0 10 13 1 1 0 0 0 10 17 1 0 0 0 0 11 14 1 0 0 0 0 11 15 1 0 0 0 0 11 18 1 1 0 0 0 12 16 1 0 0 0 0 12 19 1 0 0 0 0 13 18 2 3 0 0 0 13 20 1 0 0 0 0 14 19 1 0 0 0 0 14 21 2 0 0 0 0 15 19 1 0 0 0 0 15 24 1 1 0 0 0 16 22 2 0 0 0 0 16 23 1 0 0 0 0 17 25 1 0 0 0 0 17 26 1 0 0 0 0 20 27 1 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000437
DrugBank	DB00567
ChEMBL	CHEMBL1727
IUPHAR/BPS	4832
PharmaGKB	PA448883
KEGG Drug	D00263
PubChem CID	27447
ChEBI	3534
CAS Number	15686-71-2

Drug Properties

Molecular Weight	347.09
ALogP	-0.8185
MLogP	2.34
XLogP	-1.005
HDA	7
HBD	3
Rotatable Bonds	8
TPSA	141.52
RO5 Violation	0