NPASS drugs

Drug Information

Drug ID:	NPD2315
Drug Name:	Alprazolam
Molecular Formula:	C17H13ClN4
Canonical SMILES:	Clc1ccc2c(c1)C(=NCc1n2c(C)nn1)c1ccccc1
Standard InCHI:	InChI=1S/C17H13ClN4/c1-11-20-21-16-10-19-17(12-5-3-2-4-6-12)14-9-13(18)7-8-15(14)22(11)16/h2-9H,10H2,1H3
Standard InCHIKey:	VREFGVBLTWBCJP-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD2315

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	1026
0.1-0.2	11197
0.2-0.3	13068
0.3-0.4	2777
0.4-0.5	1811
0.5-0.6	856
0.6-0.7	151
0.7-0.8	4
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	0.768	NPC471609
Intermediate Similarity	0.7371	NPC477591
Intermediate Similarity	0.7209	NPC114209
Intermediate Similarity	0.7065	NPC317054
Remote Similarity	0.6878	NPC47596
Remote Similarity	0.6864	NPC325599
Remote Similarity	0.6825	NPC314919
Remote Similarity	0.6816	NPC476297
Remote Similarity	0.68	NPC204141
Remote Similarity	0.6788	NPC75999
Remote Similarity	0.6742	NPC40070
Remote Similarity	0.6722	NPC476219
Remote Similarity	0.6667	NPC198988
Remote Similarity	0.665	NPC314058
Remote Similarity	0.665	NPC316018
Remote Similarity	0.6628	NPC216159
Remote Similarity	0.6609	NPC315348
Remote Similarity	0.6609	NPC32002
Remote Similarity	0.6591	NPC20144
Remote Similarity	0.659	NPC125746
Remote Similarity	0.6566	NPC315617
Remote Similarity	0.6566	NPC316359
Remote Similarity	0.6559	NPC2165
Remote Similarity	0.6559	NPC195507
Remote Similarity	0.6541	NPC470203
Remote Similarity	0.6532	NPC325252
Remote Similarity	0.6529	NPC22079
Remote Similarity	0.6514	NPC104483
Remote Similarity	0.6503	NPC54102
Remote Similarity	0.6503	NPC162689
Remote Similarity	0.6494	NPC150259
Remote Similarity	0.6491	NPC475450
Remote Similarity	0.6488	NPC250361
Remote Similarity	0.6486	NPC470204
Remote Similarity	0.6481	NPC148140
Remote Similarity	0.6477	NPC115611
Remote Similarity	0.6471	NPC473587
Remote Similarity	0.6467	NPC122718
Remote Similarity	0.6467	NPC477887
Remote Similarity	0.6463	NPC317564
Remote Similarity	0.6442	NPC81561
Remote Similarity	0.6441	NPC473868
Remote Similarity	0.6441	NPC63157
Remote Similarity	0.6433	NPC475428
Remote Similarity	0.6432	NPC300238
Remote Similarity	0.6429	NPC476341
Remote Similarity	0.642	NPC88097
Remote Similarity	0.6413	NPC476464
Remote Similarity	0.6412	NPC473762
Remote Similarity	0.64	NPC314102
Remote Similarity	0.64	NPC251722
Remote Similarity	0.6395	NPC179365
Remote Similarity	0.6389	NPC143872
Remote Similarity	0.6384	NPC59084
Remote Similarity	0.6384	NPC2949
Remote Similarity	0.6358	NPC473930
Remote Similarity	0.6347	NPC41174
Remote Similarity	0.6344	NPC221786
Remote Similarity	0.6344	NPC474880
Remote Similarity	0.6344	NPC475990
Remote Similarity	0.6343	NPC218268
Remote Similarity	0.6333	NPC470440
Remote Similarity	0.633	NPC247987
Remote Similarity	0.6327	NPC83381
Remote Similarity	0.6325	NPC215519
Remote Similarity	0.631	NPC229173
Remote Similarity	0.631	NPC122141
Remote Similarity	0.6302	NPC208060
Remote Similarity	0.6298	NPC478186
Remote Similarity	0.6292	NPC284635
Remote Similarity	0.6277	NPC225018
Remote Similarity	0.6276	NPC477891
Remote Similarity	0.6264	NPC201380
Remote Similarity	0.6264	NPC470111
Remote Similarity	0.6264	NPC179787
Remote Similarity	0.6264	NPC21605
Remote Similarity	0.6263	NPC49217
Remote Similarity	0.6243	NPC162799
Remote Similarity	0.6236	NPC110126
Remote Similarity	0.6236	NPC73767
Remote Similarity	0.6232	NPC469308
Remote Similarity	0.623	NPC321911
Remote Similarity	0.623	NPC278874
Remote Similarity	0.6224	NPC16659
Remote Similarity	0.6216	NPC281094
Remote Similarity	0.6216	NPC325903
Remote Similarity	0.6215	NPC84911
Remote Similarity	0.6209	NPC288838
Remote Similarity	0.6209	NPC63545
Remote Similarity	0.6201	NPC469780
Remote Similarity	0.6201	NPC469768
Remote Similarity	0.6201	NPC238499
Remote Similarity	0.6201	NPC469783
Remote Similarity	0.6201	NPC469767
Remote Similarity	0.6201	NPC469779
Remote Similarity	0.6201	NPC469761
Remote Similarity	0.6201	NPC469784
Remote Similarity	0.6199	NPC476950
Remote Similarity	0.6196	NPC53947
Remote Similarity	0.6196	NPC33421
Remote Similarity	0.6186	NPC471579
Remote Similarity	0.6183	NPC120070
Remote Similarity	0.6175	NPC469811
Remote Similarity	0.6173	NPC265710
Remote Similarity	0.6167	NPC469766
Remote Similarity	0.6166	NPC476688
Remote Similarity	0.6166	NPC105758
Remote Similarity	0.6166	NPC476686
Remote Similarity	0.6159	NPC288232
Remote Similarity	0.6158	NPC478182
Remote Similarity	0.6158	NPC261195
Remote Similarity	0.6158	NPC96102
Remote Similarity	0.6158	NPC29886
Remote Similarity	0.6157	NPC62995
Remote Similarity	0.6145	NPC312092
Remote Similarity	0.6138	NPC255229
Remote Similarity	0.6138	NPC81229
Remote Similarity	0.6133	NPC42483
Remote Similarity	0.6131	NPC21429
Remote Similarity	0.6129	NPC232798
Remote Similarity	0.6124	NPC105127
Remote Similarity	0.6122	NPC240088
Remote Similarity	0.6122	NPC473380
Remote Similarity	0.6118	NPC46358
Remote Similarity	0.6117	NPC316910
Remote Similarity	0.6114	NPC116961
Remote Similarity	0.6114	NPC474897
Remote Similarity	0.6111	NPC307191
Remote Similarity	0.6111	NPC144114
Remote Similarity	0.6105	NPC194881
Remote Similarity	0.6085	NPC293487
Remote Similarity	0.6084	NPC192209
Remote Similarity	0.6084	NPC476566
Remote Similarity	0.6077	NPC476454
Remote Similarity	0.6077	NPC277157
Remote Similarity	0.6064	NPC51054
Remote Similarity	0.6059	NPC471593
Remote Similarity	0.6054	NPC37548
Remote Similarity	0.605	NPC108011
Remote Similarity	0.6044	NPC190296
Remote Similarity	0.6044	NPC477890
Remote Similarity	0.6037	NPC296163
Remote Similarity	0.6032	NPC236711
Remote Similarity	0.6023	NPC82295
Remote Similarity	0.6022	NPC279081
Remote Similarity	0.602	NPC469938
Remote Similarity	0.6012	NPC476140
Remote Similarity	0.6011	NPC242556
Remote Similarity	0.601	NPC478183
Remote Similarity	0.6	NPC6436
Remote Similarity	0.6	NPC169433
Remote Similarity	0.6	NPC477134
Remote Similarity	0.6	NPC206819
Remote Similarity	0.6	NPC318065
Remote Similarity	0.6	NPC56765
Remote Similarity	0.599	NPC17273
Remote Similarity	0.599	NPC135601
Remote Similarity	0.599	NPC280852
Remote Similarity	0.599	NPC271797
Remote Similarity	0.599	NPC317105
Remote Similarity	0.599	NPC21174
Remote Similarity	0.599	NPC141612
Remote Similarity	0.599	NPC478184
Remote Similarity	0.5989	NPC470233
Remote Similarity	0.5989	NPC469975
Remote Similarity	0.5982	NPC267811
Remote Similarity	0.598	NPC88110
Remote Similarity	0.5978	NPC285731
Remote Similarity	0.5978	NPC469525
Remote Similarity	0.5978	NPC314372
Remote Similarity	0.5969	NPC215584
Remote Similarity	0.5969	NPC44773
Remote Similarity	0.5968	NPC2272
Remote Similarity	0.5968	NPC187951
Remote Similarity	0.5959	NPC17751
Remote Similarity	0.5959	NPC280864
Remote Similarity	0.5957	NPC200743
Remote Similarity	0.5949	NPC91895
Remote Similarity	0.5949	NPC65080
Remote Similarity	0.5947	NPC286427
Remote Similarity	0.5947	NPC216643
Remote Similarity	0.5947	NPC129721
Remote Similarity	0.5939	NPC314141
Remote Similarity	0.5939	NPC187036
Remote Similarity	0.5938	NPC478185
Remote Similarity	0.5938	NPC224632
Remote Similarity	0.5936	NPC24678
Remote Similarity	0.5936	NPC148592
Remote Similarity	0.5936	NPC105818
Remote Similarity	0.5934	NPC230002
Remote Similarity	0.5931	NPC472289
Remote Similarity	0.5929	NPC315822
Remote Similarity	0.5928	NPC56233
Remote Similarity	0.5926	NPC470507
Remote Similarity	0.5926	NPC164802
Remote Similarity	0.5926	NPC38736
Remote Similarity	0.5916	NPC92796
Remote Similarity	0.5916	NPC135141
Remote Similarity	0.5916	NPC41257
Remote Similarity	0.5914	NPC471957

Drug Structure

NPD2315 OpenBabel08211702172D 22 25 0 0 0 0 0 0 0 0999 V2000 0.4620 -2.5460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1073 1.0372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8848 0.0623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3743 1.7174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9292 -0.2325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4187 1.4226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0915 -2.8359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2255 -2.3359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9576 -1.3359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5632 0.8113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4769 -1.5461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1962 0.4477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9576 -2.3359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0915 -0.8359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2255 -1.3359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9999 -0.0150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2406 0.1530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8236 -2.8359 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 2.5604 0.8860 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3232 -0.9463 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 1.2946 -0.9705 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1 11 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 12 2 0 0 0 0 6 12 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 16 1 0 0 0 0 10 19 1 0 0 0 0 11 20 2 0 0 0 0 11 22 1 0 0 0 0 12 17 1 0 0 0 0 13 18 1 0 0 0 0 14 15 2 0 0 0 0 14 17 1 0 0 0 0 15 22 1 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 17 19 2 0 0 0 0 20 21 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000239
DrugBank	DB00404
ChEMBL	CHEMBL661
IUPHAR/BPS	7111
PharmaGKB	PA448333
KEGG Drug	D00225
PubChem CID	2118
ChEBI	2611
CAS Number	28981-97-7

Drug Properties

Molecular Weight	308.08
ALogP	0.4906
MLogP	2.78
XLogP	5.444
HDA	4
HBD	0
Rotatable Bonds	3
TPSA	42.55
RO5 Violation	1