NPASS drugs

Drug Information

Drug ID:	NPD21
Drug Name:	Benzathine benzylpenicillin
Molecular Formula:	2C16H18N2O4S.C16H20N2
Canonical SMILES:	N(Cc1ccccc1)CCNCc1ccccc1.OC(=N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C)Cc1ccccc1.OC(=N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C)Cc1ccccc1
Standard InCHI:	InChI=1S/2C16H18N2O4S.C16H20N2/c21-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9;1-3-7-15(8-4-1)13-17-11-12-18-14-16-9-5-2-6-10-16/h23-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22);1-10,17-18H,11-14H2/t2*11-,12+,14-;/m11./s1
Standard InCHIKey:	BVGLIYRKPOITBQ-ANPZCEIESA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	DrugBank

Structural Similarity Between NPASS Natural Products and NPD21

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	78
0.1-0.2	662
0.2-0.3	4552
0.3-0.4	14933
0.4-0.5	9293
0.5-0.6	988
0.6-0.7	312
0.7-0.8	68
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
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
High Similarity	0.9313	NPC468984
Intermediate Similarity	0.8369	NPC13470
Intermediate Similarity	0.8271	NPC300315
Intermediate Similarity	0.8085	NPC322878
Intermediate Similarity	0.7857	NPC89489
Intermediate Similarity	0.7564	NPC315388
Intermediate Similarity	0.7557	NPC470544
Intermediate Similarity	0.7556	NPC6975
Intermediate Similarity	0.7551	NPC105717
Intermediate Similarity	0.7537	NPC202521
Intermediate Similarity	0.75	NPC470545
Intermediate Similarity	0.7483	NPC83790
Intermediate Similarity	0.7483	NPC128237
Intermediate Similarity	0.7466	NPC471680
Intermediate Similarity	0.7463	NPC476990
Intermediate Similarity	0.7463	NPC200964
Intermediate Similarity	0.7444	NPC470546
Intermediate Similarity	0.7413	NPC471264
Intermediate Similarity	0.7413	NPC471265
Intermediate Similarity	0.741	NPC473322
Intermediate Similarity	0.7379	NPC269398
Intermediate Similarity	0.7379	NPC263493
Intermediate Similarity	0.7375	NPC317362
Intermediate Similarity	0.7375	NPC326407
Intermediate Similarity	0.7375	NPC318930
Intermediate Similarity	0.7375	NPC317725
Intermediate Similarity	0.7353	NPC252878
Intermediate Similarity	0.7351	NPC286551
Intermediate Similarity	0.7305	NPC130309
Intermediate Similarity	0.7299	NPC46427
Intermediate Similarity	0.7293	NPC14672
Intermediate Similarity	0.7293	NPC285926
Intermediate Similarity	0.7293	NPC315276
Intermediate Similarity	0.7293	NPC239357
Intermediate Similarity	0.7292	NPC127741
Intermediate Similarity	0.7279	NPC71684
Intermediate Similarity	0.7267	NPC283783
Intermediate Similarity	0.7248	NPC329761
Intermediate Similarity	0.7248	NPC145113
Intermediate Similarity	0.7248	NPC225648
Intermediate Similarity	0.7241	NPC178662
Intermediate Similarity	0.7241	NPC92784
Intermediate Similarity	0.7241	NPC98424
Intermediate Similarity	0.7241	NPC476133
Intermediate Similarity	0.7241	NPC470884
Intermediate Similarity	0.723	NPC209509
Intermediate Similarity	0.7211	NPC161069
Intermediate Similarity	0.7197	NPC276949
Intermediate Similarity	0.7197	NPC35850
Intermediate Similarity	0.7194	NPC101719
Intermediate Similarity	0.7183	NPC255447
Intermediate Similarity	0.7162	NPC315283
Intermediate Similarity	0.7162	NPC314388
Intermediate Similarity	0.7143	NPC33742
Intermediate Similarity	0.7133	NPC246079
Intermediate Similarity	0.7122	NPC22746
Intermediate Similarity	0.7122	NPC222466
Intermediate Similarity	0.7114	NPC5620
Intermediate Similarity	0.7114	NPC315266
Intermediate Similarity	0.7114	NPC313867
Intermediate Similarity	0.7114	NPC316008
Intermediate Similarity	0.7092	NPC319766
Intermediate Similarity	0.7083	NPC287401
Intermediate Similarity	0.7075	NPC476259
Intermediate Similarity	0.7067	NPC314358
Intermediate Similarity	0.7055	NPC68865
Intermediate Similarity	0.7047	NPC476978
Intermediate Similarity	0.7034	NPC248283
Intermediate Similarity	0.7027	NPC168113
Intermediate Similarity	0.702	NPC311658
Intermediate Similarity	0.702	NPC138775
Intermediate Similarity	0.7007	NPC132636
Remote Similarity	0.6993	NPC200589
Remote Similarity	0.698	NPC139326
Remote Similarity	0.698	NPC197682
Remote Similarity	0.698	NPC176226
Remote Similarity	0.6959	NPC163392
Remote Similarity	0.6959	NPC239762
Remote Similarity	0.6957	NPC302169
Remote Similarity	0.6948	NPC162104
Remote Similarity	0.6933	NPC52748
Remote Similarity	0.6929	NPC175726
Remote Similarity	0.6929	NPC474082
Remote Similarity	0.6928	NPC2501
Remote Similarity	0.6928	NPC129666
Remote Similarity	0.6923	NPC111428
Remote Similarity	0.6923	NPC469666
Remote Similarity	0.6913	NPC469427
Remote Similarity	0.6913	NPC469426
Remote Similarity	0.6885	NPC258627
Remote Similarity	0.6863	NPC240848
Remote Similarity	0.6842	NPC262077
Remote Similarity	0.6842	NPC81026
Remote Similarity	0.6842	NPC4910
Remote Similarity	0.6835	NPC323336
Remote Similarity	0.6835	NPC326349
Remote Similarity	0.68	NPC476989
Remote Similarity	0.6797	NPC16188
Remote Similarity	0.6795	NPC122590
Remote Similarity	0.6794	NPC327481
Remote Similarity	0.6791	NPC475013
Remote Similarity	0.6779	NPC313694
Remote Similarity	0.6779	NPC242159
Remote Similarity	0.6776	NPC266741
Remote Similarity	0.6774	NPC475168
Remote Similarity	0.6774	NPC7817
Remote Similarity	0.6763	NPC329961
Remote Similarity	0.6763	NPC122427
Remote Similarity	0.6753	NPC471821
Remote Similarity	0.6753	NPC471820
Remote Similarity	0.6744	NPC329731
Remote Similarity	0.6741	NPC474584
Remote Similarity	0.6739	NPC254088
Remote Similarity	0.6731	NPC233702
Remote Similarity	0.6721	NPC325441
Remote Similarity	0.6719	NPC12730
Remote Similarity	0.6709	NPC469903
Remote Similarity	0.6691	NPC476048
Remote Similarity	0.6689	NPC141050
Remote Similarity	0.6688	NPC261934
Remote Similarity	0.6688	NPC135121
Remote Similarity	0.6688	NPC262166
Remote Similarity	0.6688	NPC5194
Remote Similarity	0.6686	NPC153554
Remote Similarity	0.6667	NPC130898
Remote Similarity	0.6667	NPC329011
Remote Similarity	0.6667	NPC474973
Remote Similarity	0.6667	NPC477217
Remote Similarity	0.6667	NPC474804
Remote Similarity	0.6667	NPC201244
Remote Similarity	0.6646	NPC470902
Remote Similarity	0.6645	NPC77905
Remote Similarity	0.6641	NPC322598
Remote Similarity	0.6626	NPC63931
Remote Similarity	0.6626	NPC472923
Remote Similarity	0.6625	NPC297145
Remote Similarity	0.6625	NPC197743
Remote Similarity	0.6623	NPC307357
Remote Similarity	0.6623	NPC268841
Remote Similarity	0.6623	NPC46098
Remote Similarity	0.661	NPC184933
Remote Similarity	0.661	NPC59827
Remote Similarity	0.6604	NPC473580
Remote Similarity	0.6594	NPC197470
Remote Similarity	0.6593	NPC319579
Remote Similarity	0.6591	NPC165538
Remote Similarity	0.6591	NPC143516
Remote Similarity	0.6585	NPC61004
Remote Similarity	0.6582	NPC56685
Remote Similarity	0.6582	NPC202198
Remote Similarity	0.6565	NPC164859
Remote Similarity	0.6561	NPC473491
Remote Similarity	0.6552	NPC477937
Remote Similarity	0.6543	NPC469902
Remote Similarity	0.6541	NPC39431
Remote Similarity	0.6534	NPC477526
Remote Similarity	0.6522	NPC324850
Remote Similarity	0.65	NPC476268
Remote Similarity	0.65	NPC477527
Remote Similarity	0.65	NPC169328
Remote Similarity	0.6484	NPC25565
Remote Similarity	0.6483	NPC474847
Remote Similarity	0.6483	NPC47667
Remote Similarity	0.6479	NPC476183
Remote Similarity	0.6478	NPC473341
Remote Similarity	0.6467	NPC475204
Remote Similarity	0.6467	NPC475123
Remote Similarity	0.6466	NPC476198
Remote Similarity	0.6466	NPC67043
Remote Similarity	0.6456	NPC324081
Remote Similarity	0.6454	NPC314992
Remote Similarity	0.6454	NPC237420
Remote Similarity	0.6454	NPC310467
Remote Similarity	0.6454	NPC220698
Remote Similarity	0.6443	NPC325479
Remote Similarity	0.6442	NPC475544
Remote Similarity	0.6442	NPC469243
Remote Similarity	0.6434	NPC476184
Remote Similarity	0.6434	NPC475439
Remote Similarity	0.6434	NPC473501
Remote Similarity	0.6434	NPC476281
Remote Similarity	0.6429	NPC2265
Remote Similarity	0.6416	NPC161143
Remote Similarity	0.6415	NPC300443
Remote Similarity	0.6398	NPC244509
Remote Similarity	0.6392	NPC254798
Remote Similarity	0.6391	NPC137627
Remote Similarity	0.6377	NPC273814
Remote Similarity	0.637	NPC4974
Remote Similarity	0.6364	NPC27833
Remote Similarity	0.6364	NPC318154
Remote Similarity	0.6358	NPC477637
Remote Similarity	0.6357	NPC3371
Remote Similarity	0.6357	NPC235421
Remote Similarity	0.6353	NPC26108
Remote Similarity	0.6349	NPC172128
Remote Similarity	0.6345	NPC476278
Remote Similarity	0.6343	NPC473418
Remote Similarity	0.6343	NPC96016
Remote Similarity	0.6341	NPC469901

Drug Structure

NPD21 OpenBabel08201723032D 70 75 0 0 1 0 0 0 0 0999 V2000 3.5032 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5032 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7811 -4.2838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5223 -5.2497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0740 -3.5767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5564 -5.5085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1081 -3.8355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8834 -5.0603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8493 -4.8014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1763 -4.3532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5032 -3.9049 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1942 -1.9538 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5032 -3.9049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5032 -2.9049 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2431 -1.6448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0032 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2103 -4.6120 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5032 -2.9049 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.4351 -3.3872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7961 -4.6120 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0352 -0.6666 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.3139 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8122 -1.9538 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 8.7345 -9.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7345 -8.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -8.2177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2071 -7.5106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7588 -9.1836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1730 -7.7694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7247 -9.4424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3978 -8.9941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4319 -8.7353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6566 -9.9601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3296 -9.5118 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2807 -8.2028 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3296 -8.5118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3296 -9.5118 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5897 -7.2517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8685 -9.0118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6225 -10.2189 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.3296 -8.5118 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.9495 -10.6672 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6225 -7.8047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5679 -7.0438 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9206 -6.5085 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2807 -9.8208 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 10.6472 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.7093 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7811 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5132 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.8433 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.7093 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7811 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5132 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.9773 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.8433 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3792 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.2452 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6472 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.1113 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6472 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.9773 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5132 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 14.1113 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.4010 -3.1284 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7079 -3.2921 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9836 -10.4083 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9424 -6.7165 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5132 -0.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.9773 -1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 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 9 2 0 0 0 0 7 9 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 10 17 2 3 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 14 1 0 0 0 0 11 17 1 6 0 0 0 12 15 1 1 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 13 18 1 0 0 0 0 13 20 2 0 0 0 0 14 18 1 0 0 0 0 14 23 1 6 0 0 0 15 21 2 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 19 65 1 0 0 0 0 22 66 1 0 0 0 0 24 39 1 0 0 0 0 25 39 1 0 0 0 0 26 27 2 0 0 0 0 26 28 1 0 0 0 0 27 29 1 0 0 0 0 28 30 2 0 0 0 0 29 32 2 0 0 0 0 30 32 1 0 0 0 0 31 32 1 0 0 0 0 31 33 1 0 0 0 0 33 40 2 3 0 0 0 33 42 1 0 0 0 0 34 36 1 0 0 0 0 34 37 1 0 0 0 0 34 40 1 6 0 0 0 35 38 1 1 0 0 0 35 39 1 0 0 0 0 35 41 1 0 0 0 0 36 41 1 0 0 0 0 36 43 2 0 0 0 0 37 41 1 0 0 0 0 37 46 1 6 0 0 0 38 44 2 0 0 0 0 38 45 1 0 0 0 0 39 46 1 0 0 0 0 42 67 1 0 0 0 0 45 68 1 0 0 0 0 47 49 2 0 0 0 0 47 50 1 0 0 0 0 48 51 2 0 0 0 0 48 52 1 0 0 0 0 49 53 1 0 0 0 0 50 54 2 0 0 0 0 51 55 1 0 0 0 0 52 56 2 0 0 0 0 53 61 2 0 0 0 0 54 61 1 0 0 0 0 55 62 2 0 0 0 0 56 62 1 0 0 0 0 57 58 1 0 0 0 0 57 63 1 0 0 0 0 58 64 1 0 0 0 0 59 61 1 0 0 0 0 59 63 1 0 0 0 0 60 62 1 0 0 0 0 60 64 1 0 0 0 0 63 69 1 0 0 0 0 64 70 1 0 0 0 0 M END $$$$

External Identifiers

TTD
DrugBank	DB09323
ChEMBL	CHEMBL3182097
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI	51352
CAS Number	1538-09-6

Drug Properties

Molecular Weight	334.10
ALogP	0.0813
MLogP	2.45
XLogP	2.874
HDA	6
HBD	2
Rotatable Bonds	8
TPSA	115.5
RO5 Violation	0