NPASS drugs

Drug Information

Drug ID:	NPD4006
Drug Name:	linotroban
Molecular Formula:	C20H23NO7S
Canonical SMILES:	CCOC(=O)C(N=C(OCc1ccccc1)O)COS(=O)(=O)c1ccc(cc1)C
Standard InCHI:	InChI=1S/C20H23NO7S/c1-3-26-19(22)18(21-20(23)27-13-16-7-5-4-6-8-16)14-28-29(24,25)17-11-9-15(2)10-12-17/h4-12,18H,3,13-14H2,1-2H3,(H,21,23)
Standard InCHIKey:	GFSFXIOOUGXOOH-UHFFFAOYSA-N
Max Developmental Stage:	Discontinued
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD4006

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	77
0.1-0.2	700
0.2-0.3	3010
0.3-0.4	9739
0.4-0.5	10643
0.5-0.6	6486
0.6-0.7	226
0.7-0.8	9
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	0.7407	NPC476278
Intermediate Similarity	0.7313	NPC476183
Intermediate Similarity	0.7259	NPC476184
Intermediate Similarity	0.7259	NPC476281
Intermediate Similarity	0.7101	NPC476260
Intermediate Similarity	0.7101	NPC476241
Intermediate Similarity	0.705	NPC476179
Intermediate Similarity	0.705	NPC476125
Intermediate Similarity	0.705	NPC4974
Remote Similarity	0.697	NPC273814
Remote Similarity	0.6934	NPC45777
Remote Similarity	0.6934	NPC477061
Remote Similarity	0.6831	NPC199738
Remote Similarity	0.6831	NPC210950
Remote Similarity	0.6812	NPC80150
Remote Similarity	0.6772	NPC316797
Remote Similarity	0.677	NPC313375
Remote Similarity	0.677	NPC314725
Remote Similarity	0.6714	NPC160493
Remote Similarity	0.6667	NPC311753
Remote Similarity	0.6667	NPC119631
Remote Similarity	0.6639	NPC220893
Remote Similarity	0.6612	NPC89377
Remote Similarity	0.6599	NPC470392
Remote Similarity	0.6587	NPC3371
Remote Similarity	0.6583	NPC58616
Remote Similarity	0.6571	NPC190663
Remote Similarity	0.6565	NPC211551
Remote Similarity	0.6536	NPC106183
Remote Similarity	0.6533	NPC477557
Remote Similarity	0.6504	NPC173443
Remote Similarity	0.6479	NPC142577
Remote Similarity	0.6475	NPC169328
Remote Similarity	0.6462	NPC318154
Remote Similarity	0.6452	NPC213156
Remote Similarity	0.6452	NPC240108
Remote Similarity	0.6439	NPC269457
Remote Similarity	0.6429	NPC310467
Remote Similarity	0.6423	NPC304760
Remote Similarity	0.6419	NPC45191
Remote Similarity	0.6419	NPC246913
Remote Similarity	0.6391	NPC472315
Remote Similarity	0.6391	NPC474376
Remote Similarity	0.6391	NPC472316
Remote Similarity	0.6391	NPC475203
Remote Similarity	0.637	NPC476353
Remote Similarity	0.6364	NPC474862
Remote Similarity	0.6357	NPC475954
Remote Similarity	0.635	NPC265002
Remote Similarity	0.6345	NPC47667
Remote Similarity	0.6327	NPC296712
Remote Similarity	0.632	NPC258627
Remote Similarity	0.6312	NPC237420
Remote Similarity	0.6309	NPC246079
Remote Similarity	0.6308	NPC118343
Remote Similarity	0.6288	NPC474365
Remote Similarity	0.6288	NPC301943
Remote Similarity	0.6279	NPC33168
Remote Similarity	0.6277	NPC234376
Remote Similarity	0.6277	NPC269340
Remote Similarity	0.6276	NPC138798
Remote Similarity	0.6269	NPC136962
Remote Similarity	0.6267	NPC471953
Remote Similarity	0.6266	NPC132771
Remote Similarity	0.626	NPC42211
Remote Similarity	0.625	NPC165212
Remote Similarity	0.625	NPC26285
Remote Similarity	0.625	NPC6570
Remote Similarity	0.6241	NPC254088
Remote Similarity	0.6234	NPC197921
Remote Similarity	0.6231	NPC78701
Remote Similarity	0.6231	NPC35448
Remote Similarity	0.622	NPC265521
Remote Similarity	0.6209	NPC281104
Remote Similarity	0.6204	NPC323007
Remote Similarity	0.6204	NPC183700
Remote Similarity	0.6204	NPC319579
Remote Similarity	0.6204	NPC63345
Remote Similarity	0.6202	NPC30361
Remote Similarity	0.62	NPC326966
Remote Similarity	0.6197	NPC5932
Remote Similarity	0.6196	NPC56635
Remote Similarity	0.6194	NPC91953
Remote Similarity	0.6194	NPC472919
Remote Similarity	0.6194	NPC469360
Remote Similarity	0.619	NPC185501
Remote Similarity	0.6187	NPC474363
Remote Similarity	0.6187	NPC1986
Remote Similarity	0.6187	NPC474544
Remote Similarity	0.6187	NPC172525
Remote Similarity	0.6184	NPC284855
Remote Similarity	0.6184	NPC282477
Remote Similarity	0.6183	NPC12730
Remote Similarity	0.6183	NPC146351
Remote Similarity	0.6181	NPC229600
Remote Similarity	0.6176	NPC206341
Remote Similarity	0.6176	NPC182549
Remote Similarity	0.6176	NPC114741
Remote Similarity	0.6176	NPC469511
Remote Similarity	0.6174	NPC325651
Remote Similarity	0.6165	NPC234305
Remote Similarity	0.6164	NPC211218
Remote Similarity	0.616	NPC325441
Remote Similarity	0.6159	NPC244866
Remote Similarity	0.6159	NPC227553
Remote Similarity	0.6154	NPC256369
Remote Similarity	0.6154	NPC270654
Remote Similarity	0.6154	NPC14950
Remote Similarity	0.6154	NPC249912
Remote Similarity	0.6154	NPC276775
Remote Similarity	0.6154	NPC319950
Remote Similarity	0.6154	NPC92754
Remote Similarity	0.6149	NPC286551
Remote Similarity	0.6144	NPC127741
Remote Similarity	0.6139	NPC136951
Remote Similarity	0.6139	NPC97004
Remote Similarity	0.6139	NPC161155
Remote Similarity	0.6138	NPC213126
Remote Similarity	0.6138	NPC317474
Remote Similarity	0.6138	NPC84281
Remote Similarity	0.6138	NPC169485
Remote Similarity	0.6138	NPC291027
Remote Similarity	0.6135	NPC206372
Remote Similarity	0.6135	NPC203424
Remote Similarity	0.6131	NPC292758
Remote Similarity	0.6131	NPC24777
Remote Similarity	0.6131	NPC273837
Remote Similarity	0.6131	NPC65855
Remote Similarity	0.6127	NPC323948
Remote Similarity	0.6124	NPC5472
Remote Similarity	0.6119	NPC171831
Remote Similarity	0.6119	NPC280616
Remote Similarity	0.6119	NPC85977
Remote Similarity	0.6119	NPC242913
Remote Similarity	0.6118	NPC90693
Remote Similarity	0.6118	NPC64897
Remote Similarity	0.6115	NPC473922
Remote Similarity	0.6111	NPC263835
Remote Similarity	0.6111	NPC478016
Remote Similarity	0.6111	NPC9822
Remote Similarity	0.6111	NPC478014
Remote Similarity	0.6111	NPC478015
Remote Similarity	0.6107	NPC225060
Remote Similarity	0.6103	NPC277788
Remote Similarity	0.6103	NPC20485
Remote Similarity	0.6103	NPC260952
Remote Similarity	0.6101	NPC97282
Remote Similarity	0.6099	NPC197470
Remote Similarity	0.6099	NPC471616
Remote Similarity	0.6099	NPC303370
Remote Similarity	0.6098	NPC212699
Remote Similarity	0.6098	NPC207675
Remote Similarity	0.6096	NPC35996
Remote Similarity	0.6095	NPC208280
Remote Similarity	0.609	NPC212850
Remote Similarity	0.609	NPC83289
Remote Similarity	0.609	NPC189724
Remote Similarity	0.6087	NPC476003
Remote Similarity	0.6087	NPC30563
Remote Similarity	0.6084	NPC254233
Remote Similarity	0.6081	NPC65310
Remote Similarity	0.6081	NPC476033
Remote Similarity	0.6077	NPC317400
Remote Similarity	0.6076	NPC63628
Remote Similarity	0.6076	NPC178466
Remote Similarity	0.6074	NPC152384
Remote Similarity	0.6074	NPC37714
Remote Similarity	0.6071	NPC153053
Remote Similarity	0.6071	NPC87069
Remote Similarity	0.6071	NPC120217
Remote Similarity	0.6067	NPC69496
Remote Similarity	0.6066	NPC323103
Remote Similarity	0.6066	NPC103387
Remote Similarity	0.6063	NPC172128
Remote Similarity	0.6061	NPC325497
Remote Similarity	0.6061	NPC98911
Remote Similarity	0.6061	NPC472318
Remote Similarity	0.6058	NPC17417
Remote Similarity	0.6058	NPC469636
Remote Similarity	0.6058	NPC281604
Remote Similarity	0.6058	NPC10251
Remote Similarity	0.6053	NPC233910
Remote Similarity	0.6053	NPC245836
Remote Similarity	0.6048	NPC475710
Remote Similarity	0.6047	NPC23453
Remote Similarity	0.6043	NPC321852
Remote Similarity	0.6043	NPC158282
Remote Similarity	0.6043	NPC185840
Remote Similarity	0.6043	NPC163674
Remote Similarity	0.6042	NPC43275
Remote Similarity	0.604	NPC114096
Remote Similarity	0.6038	NPC477556
Remote Similarity	0.6033	NPC121800
Remote Similarity	0.6031	NPC325499
Remote Similarity	0.6029	NPC37115
Remote Similarity	0.6029	NPC477251
Remote Similarity	0.6029	NPC327481
Remote Similarity	0.6028	NPC469509
Remote Similarity	0.6028	NPC29607
Remote Similarity	0.6026	NPC239770

Drug Structure

NPD4006 OpenBabel08211704332D 30 31 0 0 1 0 0 0 0 0999 V2000 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 15 1 0 0 0 0 3 26 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 16 2 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 15 2 0 0 0 0 10 12 2 0 0 0 0 10 15 1 0 0 0 0 11 17 2 0 0 0 0 12 17 1 0 0 0 0 13 16 1 0 0 0 0 13 27 1 0 0 0 0 14 18 1 0 0 0 0 14 28 1 0 0 0 0 17 29 1 0 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 19 22 2 0 0 0 0 19 26 1 0 0 0 0 20 21 2 3 0 0 0 20 23 1 0 0 0 0 20 27 1 0 0 0 0 23 30 1 0 0 0 0 24 29 2 0 0 0 0 25 29 2 0 0 0 0 28 29 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB016317
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	421.12
ALogP	0.8461
MLogP	2.67
XLogP	4.505
HDA	8
HBD	1
Rotatable Bonds	14
TPSA	119.87
RO5 Violation	1