NPASS drugs

Drug Information

Drug ID:	NPD5557
Drug Name:	Lefradafiban
Molecular Formula:	C23H25N3O6
Canonical SMILES:	COC(=O)C[C@@H]1C[C@H](N=C1O)COc1ccc(cc1)c1ccc(cc1)C(=NC(=O)OC)N
Standard InCHI:	InChI=1S/C23H25N3O6/c1-30-20(27)12-17-11-18(25-22(17)28)13-32-19-9-7-15(8-10-19)14-3-5-16(6-4-14)21(24)26-23(29)31-2/h3-10,17-18H,11-13H2,1-2H3,(H,25,28)(H2,24,26,29)/t17-,18-/m0/s1
Standard InCHIKey:	PGCFXITVMNNKON-ROUUACIJSA-N
Max Developmental Stage:	Phase 1
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD5557

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	161
0.1-0.2	839
0.2-0.3	2732
0.3-0.4	8840
0.4-0.5	3761
0.5-0.6	12572
0.6-0.7	1956
0.7-0.8	29
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	0.7578	NPC470392
Intermediate Similarity	0.7414	NPC212699
Intermediate Similarity	0.7414	NPC207675
Intermediate Similarity	0.7412	NPC132771
Intermediate Similarity	0.7394	NPC283207
Intermediate Similarity	0.7353	NPC313414
Intermediate Similarity	0.7314	NPC56635
Intermediate Similarity	0.7273	NPC315542
Intermediate Similarity	0.7247	NPC67080
Intermediate Similarity	0.7212	NPC169766
Intermediate Similarity	0.7174	NPC88378
Intermediate Similarity	0.7174	NPC211713
Intermediate Similarity	0.716	NPC91953
Intermediate Similarity	0.7101	NPC197921
Intermediate Similarity	0.7081	NPC477115
Intermediate Similarity	0.7072	NPC71205
Intermediate Similarity	0.7059	NPC83289
Intermediate Similarity	0.7059	NPC189724
Intermediate Similarity	0.7059	NPC469360
Intermediate Similarity	0.7059	NPC212850
Intermediate Similarity	0.7048	NPC471953
Intermediate Similarity	0.7041	NPC471316
Intermediate Similarity	0.7027	NPC474953
Intermediate Similarity	0.7019	NPC471314
Intermediate Similarity	0.7019	NPC471315
Intermediate Similarity	0.7017	NPC293164
Intermediate Similarity	0.7017	NPC471394
Intermediate Similarity	0.7012	NPC296712
Intermediate Similarity	0.7	NPC156348
Remote Similarity	0.6994	NPC29477
Remote Similarity	0.6989	NPC182119
Remote Similarity	0.6988	NPC326966
Remote Similarity	0.6983	NPC319320
Remote Similarity	0.6983	NPC287757
Remote Similarity	0.6978	NPC254700
Remote Similarity	0.6975	NPC211218
Remote Similarity	0.697	NPC325651
Remote Similarity	0.6966	NPC275027
Remote Similarity	0.6966	NPC18614
Remote Similarity	0.6952	NPC474902
Remote Similarity	0.6937	NPC263835
Remote Similarity	0.6933	NPC95733
Remote Similarity	0.6933	NPC62101
Remote Similarity	0.6927	NPC469830
Remote Similarity	0.6927	NPC4910
Remote Similarity	0.6923	NPC472923
Remote Similarity	0.6915	NPC475421
Remote Similarity	0.6911	NPC299806
Remote Similarity	0.691	NPC52475
Remote Similarity	0.6907	NPC477526
Remote Similarity	0.6901	NPC259800
Remote Similarity	0.6901	NPC241086
Remote Similarity	0.6901	NPC282087
Remote Similarity	0.6901	NPC328137
Remote Similarity	0.6901	NPC317741
Remote Similarity	0.6901	NPC318984
Remote Similarity	0.6901	NPC318028
Remote Similarity	0.6897	NPC247298
Remote Similarity	0.6895	NPC475794
Remote Similarity	0.6895	NPC469831
Remote Similarity	0.6888	NPC184933
Remote Similarity	0.6888	NPC59827
Remote Similarity	0.6886	NPC45191
Remote Similarity	0.6885	NPC15506
Remote Similarity	0.6875	NPC115144
Remote Similarity	0.6875	NPC277857
Remote Similarity	0.6875	NPC324081
Remote Similarity	0.6875	NPC43275
Remote Similarity	0.6868	NPC22014
Remote Similarity	0.6859	NPC469829
Remote Similarity	0.6857	NPC17760
Remote Similarity	0.6852	NPC474862
Remote Similarity	0.6848	NPC473502
Remote Similarity	0.6845	NPC244866
Remote Similarity	0.6845	NPC476227
Remote Similarity	0.6845	NPC471165
Remote Similarity	0.6839	NPC329731
Remote Similarity	0.6824	NPC6570
Remote Similarity	0.6823	NPC474650
Remote Similarity	0.6823	NPC235194
Remote Similarity	0.6821	NPC28510
Remote Similarity	0.6818	NPC245974
Remote Similarity	0.6813	NPC206736
Remote Similarity	0.6813	NPC195766
Remote Similarity	0.6806	NPC470903
Remote Similarity	0.6806	NPC470112
Remote Similarity	0.6806	NPC167763
Remote Similarity	0.6804	NPC471395
Remote Similarity	0.6804	NPC474661
Remote Similarity	0.6804	NPC475919
Remote Similarity	0.6802	NPC326860
Remote Similarity	0.6802	NPC197239
Remote Similarity	0.68	NPC161155
Remote Similarity	0.68	NPC136951
Remote Similarity	0.68	NPC97004
Remote Similarity	0.6791	NPC306804
Remote Similarity	0.6789	NPC271958
Remote Similarity	0.6789	NPC45112
Remote Similarity	0.6789	NPC263507
Remote Similarity	0.6789	NPC134413
Remote Similarity	0.6784	NPC477527
Remote Similarity	0.6784	NPC473052
Remote Similarity	0.6784	NPC473055
Remote Similarity	0.6774	NPC151030
Remote Similarity	0.6774	NPC269383
Remote Similarity	0.6771	NPC474607
Remote Similarity	0.6769	NPC64140
Remote Similarity	0.6769	NPC174122
Remote Similarity	0.6766	NPC478147
Remote Similarity	0.6761	NPC97282
Remote Similarity	0.6757	NPC314861
Remote Similarity	0.6755	NPC164608
Remote Similarity	0.6748	NPC14390
Remote Similarity	0.6746	NPC328070
Remote Similarity	0.6744	NPC322526
Remote Similarity	0.6743	NPC63628
Remote Similarity	0.6743	NPC178466
Remote Similarity	0.6737	NPC194671
Remote Similarity	0.6737	NPC269750
Remote Similarity	0.6736	NPC138083
Remote Similarity	0.6735	NPC470642
Remote Similarity	0.6728	NPC289330
Remote Similarity	0.6728	NPC17388
Remote Similarity	0.6728	NPC53596
Remote Similarity	0.6728	NPC471308
Remote Similarity	0.6728	NPC160120
Remote Similarity	0.6727	NPC4974
Remote Similarity	0.6725	NPC196708
Remote Similarity	0.6725	NPC6913
Remote Similarity	0.6724	NPC204546
Remote Similarity	0.6718	NPC234069
Remote Similarity	0.6716	NPC242728
Remote Similarity	0.6706	NPC105541
Remote Similarity	0.6705	NPC299583
Remote Similarity	0.6703	NPC314725
Remote Similarity	0.6703	NPC313375
Remote Similarity	0.6702	NPC273755
Remote Similarity	0.6685	NPC329837
Remote Similarity	0.6684	NPC196091
Remote Similarity	0.6684	NPC68328
Remote Similarity	0.6684	NPC40234
Remote Similarity	0.6667	NPC294516
Remote Similarity	0.6667	NPC265473
Remote Similarity	0.6667	NPC478189
Remote Similarity	0.6667	NPC276665
Remote Similarity	0.6667	NPC26108
Remote Similarity	0.6667	NPC218530
Remote Similarity	0.6667	NPC203972
Remote Similarity	0.6667	NPC107938
Remote Similarity	0.6667	NPC476194
Remote Similarity	0.665	NPC473378
Remote Similarity	0.665	NPC473407
Remote Similarity	0.665	NPC474077
Remote Similarity	0.6649	NPC89831
Remote Similarity	0.6648	NPC140915
Remote Similarity	0.6648	NPC262216
Remote Similarity	0.6648	NPC305700
Remote Similarity	0.6648	NPC197741
Remote Similarity	0.6648	NPC470019
Remote Similarity	0.6648	NPC18249
Remote Similarity	0.6648	NPC187028
Remote Similarity	0.6648	NPC10221
Remote Similarity	0.6647	NPC471201
Remote Similarity	0.6647	NPC274732
Remote Similarity	0.6646	NPC27581
Remote Similarity	0.6633	NPC469816
Remote Similarity	0.6633	NPC469815
Remote Similarity	0.6632	NPC86678
Remote Similarity	0.6632	NPC50016
Remote Similarity	0.663	NPC123011
Remote Similarity	0.663	NPC256689
Remote Similarity	0.6629	NPC66518
Remote Similarity	0.6629	NPC290404
Remote Similarity	0.6625	NPC51345
Remote Similarity	0.6617	NPC124302
Remote Similarity	0.6617	NPC477550
Remote Similarity	0.6617	NPC14622
Remote Similarity	0.6617	NPC70290
Remote Similarity	0.6617	NPC46744
Remote Similarity	0.6617	NPC477552
Remote Similarity	0.6617	NPC73020
Remote Similarity	0.6617	NPC215098
Remote Similarity	0.6616	NPC204970
Remote Similarity	0.6615	NPC32064
Remote Similarity	0.6614	NPC137627
Remote Similarity	0.6614	NPC49315
Remote Similarity	0.6613	NPC61004
Remote Similarity	0.6609	NPC239770
Remote Similarity	0.6608	NPC90693
Remote Similarity	0.6608	NPC64897
Remote Similarity	0.6608	NPC132308
Remote Similarity	0.66	NPC149962
Remote Similarity	0.6599	NPC61332
Remote Similarity	0.6599	NPC240130
Remote Similarity	0.6598	NPC315913
Remote Similarity	0.6597	NPC228040
Remote Similarity	0.6596	NPC473693
Remote Similarity	0.6596	NPC46009
Remote Similarity	0.6596	NPC471568
Remote Similarity	0.6596	NPC475123

Drug Structure

NPD5557 OpenBabel08211708292D 35 37 0 0 1 0 0 0 0 0999 V2000 -4.4736 -2.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2013 -1.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0052 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1391 -0.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8712 0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0052 -1.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4071 0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2731 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5411 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4071 2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6180 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8968 -1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1391 0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2731 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8712 -0.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 -0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8090 0.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5411 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8913 -1.6555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7372 -1.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4693 -1.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7372 -2.4122 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 -8.6032 -0.9122 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.2981 -0.7420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 -1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4693 -2.4122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4791 -2.4646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3353 -0.9122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6750 2.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8712 -2.9122 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6032 -2.9122 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1280 -2.6736 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 30 1 0 0 0 0 2 31 1 0 0 0 0 3 5 1 0 0 0 0 3 14 2 0 0 0 0 4 6 2 0 0 0 0 4 14 1 0 0 0 0 5 16 2 0 0 0 0 6 16 1 0 0 0 0 7 9 1 0 0 0 0 7 15 2 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 19 2 0 0 0 0 10 19 1 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 12 20 1 0 0 0 0 13 32 1 0 0 0 0 14 15 1 0 0 0 0 16 21 1 0 0 0 0 17 12 1 6 0 0 0 17 22 1 0 0 0 0 18 13 1 1 0 0 0 18 25 1 0 0 0 0 19 32 1 0 0 0 0 20 27 2 0 0 0 0 20 30 1 0 0 0 0 21 24 1 0 0 0 0 21 26 2 3 0 0 0 22 25 2 0 0 0 0 22 28 1 0 0 0 0 23 26 1 0 0 0 0 23 29 2 0 0 0 0 23 31 1 0 0 0 0 24 33 1 0 0 0 0 24 34 1 0 0 0 0 28 35 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB007767
DrugBank	DB04863
ChEMBL	CHEMBL2105032
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI	60634
CAS Number	149503-79-7

Drug Properties

Molecular Weight	439.17
ALogP	-0.8229
MLogP	3
XLogP	3.882
HDA	8
HBD	2
Rotatable Bonds	14
TPSA	132.8
RO5 Violation	0