NPASS drugs

Drug Information

Drug ID:	NPD1500
Drug Name:	Lorazepam
Molecular Formula:	C15H10Cl2N2O2
Canonical SMILES:	Clc1ccc2c(c1)C(=NC(C(=N2)O)O)c1ccccc1Cl
Standard InCHI:	InChI=1S/C15H10Cl2N2O2/c16-8-5-6-12-10(7-8)13(19-15(21)14(20)18-12)9-3-1-2-4-11(9)17/h1-7,15,21H,(H,18,20)
Standard InCHIKey:	DIWRORZWFLOCLC-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD1500

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	139
0.1-0.2	2340
0.2-0.3	11396
0.3-0.4	12361
0.4-0.5	3806
0.5-0.6	811
0.6-0.7	35
0.7-0.8	1
0.8-0.85	0
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	0.918	NPC317564
Intermediate Similarity	0.766	NPC325599
Remote Similarity	0.6918	NPC313352
Remote Similarity	0.6748	NPC78154
Remote Similarity	0.6736	NPC476950
Remote Similarity	0.6575	NPC197680
Remote Similarity	0.6575	NPC259098
Remote Similarity	0.6458	NPC283130
Remote Similarity	0.6458	NPC328683
Remote Similarity	0.6449	NPC187036
Remote Similarity	0.6429	NPC147957
Remote Similarity	0.641	NPC477890
Remote Similarity	0.6403	NPC205652
Remote Similarity	0.6395	NPC478079
Remote Similarity	0.6324	NPC302790
Remote Similarity	0.6316	NPC178681
Remote Similarity	0.6316	NPC471310
Remote Similarity	0.6286	NPC470550
Remote Similarity	0.6268	NPC192209
Remote Similarity	0.6222	NPC313810
Remote Similarity	0.6214	NPC296163
Remote Similarity	0.6154	NPC313449
Remote Similarity	0.6149	NPC321617
Remote Similarity	0.6145	NPC477591
Remote Similarity	0.6103	NPC474559
Remote Similarity	0.6082	NPC116961
Remote Similarity	0.6078	NPC256893
Remote Similarity	0.6077	NPC476483
Remote Similarity	0.6065	NPC159589
Remote Similarity	0.6051	NPC243162
Remote Similarity	0.6048	NPC15839
Remote Similarity	0.6026	NPC101372
Remote Similarity	0.6016	NPC307456
Remote Similarity	0.6014	NPC37584
Remote Similarity	0.6013	NPC315348
Remote Similarity	0.6013	NPC32002
Remote Similarity	0.6	NPC264580
Remote Similarity	0.5987	NPC226662
Remote Similarity	0.5986	NPC314141
Remote Similarity	0.5985	NPC211551
Remote Similarity	0.5971	NPC164802
Remote Similarity	0.5969	NPC191444
Remote Similarity	0.5964	NPC470507
Remote Similarity	0.5959	NPC162689
Remote Similarity	0.5959	NPC54102
Remote Similarity	0.5944	NPC471318
Remote Similarity	0.594	NPC311242
Remote Similarity	0.5935	NPC184437
Remote Similarity	0.5933	NPC325013
Remote Similarity	0.5931	NPC148140
Remote Similarity	0.5923	NPC226438
Remote Similarity	0.5912	NPC232872
Remote Similarity	0.5906	NPC203076
Remote Similarity	0.5903	NPC288232
Remote Similarity	0.5891	NPC176858
Remote Similarity	0.589	NPC81561
Remote Similarity	0.5878	NPC108800
Remote Similarity	0.5872	NPC238430
Remote Similarity	0.5868	NPC471458
Remote Similarity	0.5862	NPC470498
Remote Similarity	0.5859	NPC473031
Remote Similarity	0.5857	NPC77294
Remote Similarity	0.5855	NPC469949
Remote Similarity	0.5843	NPC314919
Remote Similarity	0.5823	NPC122553
Remote Similarity	0.5819	NPC293472
Remote Similarity	0.5818	NPC37548
Remote Similarity	0.5814	NPC262393
Remote Similarity	0.5814	NPC12429
Remote Similarity	0.5811	NPC316582
Remote Similarity	0.581	NPC192270
Remote Similarity	0.5802	NPC245259
Remote Similarity	0.5799	NPC477887
Remote Similarity	0.5793	NPC254798
Remote Similarity	0.5789	NPC303045
Remote Similarity	0.5789	NPC161972
Remote Similarity	0.5786	NPC471312
Remote Similarity	0.5779	NPC9856
Remote Similarity	0.5776	NPC477155
Remote Similarity	0.5772	NPC215519
Remote Similarity	0.5769	NPC470877
Remote Similarity	0.5767	NPC242556
Remote Similarity	0.5762	NPC317758
Remote Similarity	0.5753	NPC125416
Remote Similarity	0.574	NPC477156
Remote Similarity	0.574	NPC476464
Remote Similarity	0.574	NPC477157
Remote Similarity	0.5736	NPC471638
Remote Similarity	0.5735	NPC323726
Remote Similarity	0.5732	NPC324445
Remote Similarity	0.5731	NPC473320
Remote Similarity	0.5725	NPC471307
Remote Similarity	0.5725	NPC159178
Remote Similarity	0.5725	NPC121872
Remote Similarity	0.5725	NPC172128
Remote Similarity	0.5725	NPC209764
Remote Similarity	0.5725	NPC141139
Remote Similarity	0.5725	NPC78041
Remote Similarity	0.5725	NPC74936
Remote Similarity	0.5724	NPC122718
Remote Similarity	0.5724	NPC474926
Remote Similarity	0.5723	NPC187951
Remote Similarity	0.5714	NPC471132
Remote Similarity	0.5714	NPC104483
Remote Similarity	0.5714	NPC471574
Remote Similarity	0.5706	NPC472103
Remote Similarity	0.5706	NPC190296
Remote Similarity	0.5706	NPC469762
Remote Similarity	0.5705	NPC22079
Remote Similarity	0.5705	NPC476687
Remote Similarity	0.5705	NPC476685
Remote Similarity	0.5705	NPC476689
Remote Similarity	0.5693	NPC469457
Remote Similarity	0.5692	NPC111233
Remote Similarity	0.569	NPC54988
Remote Similarity	0.5683	NPC194390
Remote Similarity	0.5683	NPC224610
Remote Similarity	0.5683	NPC88267
Remote Similarity	0.5683	NPC113326
Remote Similarity	0.5682	NPC158129
Remote Similarity	0.568	NPC38736
Remote Similarity	0.5676	NPC228515
Remote Similarity	0.5674	NPC288785
Remote Similarity	0.5671	NPC116519
Remote Similarity	0.5665	NPC40779
Remote Similarity	0.5658	NPC46358
Remote Similarity	0.5655	NPC184161
Remote Similarity	0.5652	NPC291610
Remote Similarity	0.5649	NPC250361
Remote Similarity	0.5647	NPC115049
Remote Similarity	0.5647	NPC10730
Remote Similarity	0.5647	NPC285469
Remote Similarity	0.5647	NPC141353
Remote Similarity	0.5647	NPC469785
Remote Similarity	0.5647	NPC10875
Remote Similarity	0.5644	NPC314287
Remote Similarity	0.5636	NPC159856
Remote Similarity	0.5636	NPC314372
Remote Similarity	0.5636	NPC472100
Remote Similarity	0.563	NPC25565
Remote Similarity	0.5629	NPC124005
Remote Similarity	0.5615	NPC262295
Remote Similarity	0.5613	NPC150863
Remote Similarity	0.5611	NPC133261
Remote Similarity	0.5611	NPC270009
Remote Similarity	0.561	NPC136002
Remote Similarity	0.5607	NPC476231
Remote Similarity	0.5606	NPC316108
Remote Similarity	0.5605	NPC40364
Remote Similarity	0.5604	NPC83381

Drug Structure

NPD1500 OpenBabel08211701082D 23 25 0 0 1 0 0 0 0 0999 V2000 2.5233 -1.4972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5233 -2.4972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6573 -0.9972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6573 -2.9972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3671 -2.9209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5896 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6784 -2.5355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4115 -3.2156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7913 -1.4972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9010 -1.5605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7913 -2.4972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8565 -1.2658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0747 -0.9972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7219 0.5311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7331 0.6802 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.1890 -4.1906 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -0.0747 -2.9972 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -2.2219 -0.3349 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2852 1.3574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4383 1.6357 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8513 2.2583 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1185 2.3688 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 9 2 0 0 0 0 4 11 2 0 0 0 0 5 6 2 0 0 0 0 5 8 1 0 0 0 0 6 12 1 0 0 0 0 7 8 2 0 0 0 0 7 10 1 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 13 1 0 0 0 0 10 12 2 0 0 0 0 10 13 1 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 19 2 0 0 0 0 14 15 1 0 0 0 0 14 18 2 0 0 0 0 14 20 1 0 0 0 0 15 19 1 0 0 0 0 15 21 1 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000237
DrugBank	DB00186
ChEMBL	CHEMBL580
IUPHAR/BPS	5884
PharmaGKB	PA450267
KEGG Drug	D00365
PubChem CID	3958
ChEBI	6539
CAS Number	846-49-1

Drug Properties

Molecular Weight	320.01
ALogP	0.9787
MLogP	2.45
XLogP	4.039
HDA	4
HBD	2
Rotatable Bonds	5
TPSA	65.18
RO5 Violation	0