NPASS drugs

Drug Information

Drug ID:	NPD5543
Drug Name:
Molecular Formula:	C23H25ClN2O9
Canonical SMILES:	OCN/C(=C/1C(=O)[C@@H](N(C)C)[C@H]2[C@](C1=O)(O)C(=O)C1=C(O)c3c([C@@]([C@H]1C2)(C)O)c(Cl)ccc3O)/O
Standard InCHI:	InChI=1S/C23H25ClN2O9/c1-22(34)8-6-9-16(26(2)3)18(30)14(21(33)25-7-27)20(32)23(9,35)19(31)12(8)17(29)13-11(28)5-4-10(24)15(13)22/h4-5,8-9,16,25,27-29,33-35H,6-7H2,1-3H3/b21-14-/t8-,9-,16-,22-,23-/m0/s1
Standard InCHIKey:	BXVOHUQQUBSHLD-XCTBDMBQSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD5543

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	236
0.1-0.2	1171
0.2-0.3	3637
0.3-0.4	8933
0.4-0.5	7715
0.5-0.6	9010
0.6-0.7	183
0.7-0.8	4
0.8-0.85	1
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	0.801	NPC96730
Intermediate Similarity	0.799	NPC39528
Intermediate Similarity	0.7259	NPC295531
Intermediate Similarity	0.7179	NPC291305
Intermediate Similarity	0.7056	NPC469973
Remote Similarity	0.6798	NPC329790
Remote Similarity	0.672	NPC2672
Remote Similarity	0.6606	NPC313582
Remote Similarity	0.6492	NPC68967
Remote Similarity	0.6476	NPC264938
Remote Similarity	0.6439	NPC298339
Remote Similarity	0.6432	NPC317727
Remote Similarity	0.6372	NPC316164
Remote Similarity	0.6368	NPC12890
Remote Similarity	0.635	NPC314693
Remote Similarity	0.635	NPC195392
Remote Similarity	0.6301	NPC314596
Remote Similarity	0.63	NPC101207
Remote Similarity	0.6293	NPC474857
Remote Similarity	0.6281	NPC470559
Remote Similarity	0.6279	NPC42286
Remote Similarity	0.6267	NPC244191
Remote Similarity	0.6263	NPC474861
Remote Similarity	0.6263	NPC470564
Remote Similarity	0.6263	NPC472623
Remote Similarity	0.6263	NPC280497
Remote Similarity	0.6262	NPC279665
Remote Similarity	0.6257	NPC238108
Remote Similarity	0.6256	NPC315520
Remote Similarity	0.6256	NPC131078
Remote Similarity	0.6256	NPC301846
Remote Similarity	0.6256	NPC191606
Remote Similarity	0.6256	NPC314946
Remote Similarity	0.625	NPC109403
Remote Similarity	0.625	NPC313274
Remote Similarity	0.625	NPC261012
Remote Similarity	0.625	NPC314738
Remote Similarity	0.6244	NPC329969
Remote Similarity	0.6238	NPC470081
Remote Similarity	0.6232	NPC264922
Remote Similarity	0.6226	NPC196231
Remote Similarity	0.6222	NPC87985
Remote Similarity	0.6219	NPC209377
Remote Similarity	0.6212	NPC314257
Remote Similarity	0.6211	NPC297322
Remote Similarity	0.621	NPC314941
Remote Similarity	0.6203	NPC272268
Remote Similarity	0.6199	NPC315889
Remote Similarity	0.6196	NPC149379
Remote Similarity	0.6195	NPC108948
Remote Similarity	0.6195	NPC184518
Remote Similarity	0.619	NPC151292
Remote Similarity	0.6188	NPC56887
Remote Similarity	0.6188	NPC193853
Remote Similarity	0.6188	NPC223077
Remote Similarity	0.6186	NPC66909
Remote Similarity	0.6186	NPC281629
Remote Similarity	0.6184	NPC73555
Remote Similarity	0.6178	NPC85310
Remote Similarity	0.6178	NPC469520
Remote Similarity	0.6175	NPC313541
Remote Similarity	0.617	NPC475957
Remote Similarity	0.6165	NPC277865
Remote Similarity	0.6162	NPC182921
Remote Similarity	0.6162	NPC472211
Remote Similarity	0.6162	NPC474824
Remote Similarity	0.6162	NPC218870
Remote Similarity	0.6162	NPC29647
Remote Similarity	0.6162	NPC470408
Remote Similarity	0.6157	NPC315351
Remote Similarity	0.6157	NPC293624
Remote Similarity	0.6157	NPC316412
Remote Similarity	0.615	NPC475780
Remote Similarity	0.615	NPC472404
Remote Similarity	0.6147	NPC64576
Remote Similarity	0.6147	NPC254045
Remote Similarity	0.6147	NPC151470
Remote Similarity	0.6147	NPC201055
Remote Similarity	0.6144	NPC328287
Remote Similarity	0.6139	NPC255607
Remote Similarity	0.6139	NPC3375
Remote Similarity	0.6133	NPC315253
Remote Similarity	0.6132	NPC51047
Remote Similarity	0.6131	NPC79328
Remote Similarity	0.6129	NPC115458
Remote Similarity	0.6127	NPC73544
Remote Similarity	0.6127	NPC163924
Remote Similarity	0.6127	NPC54661
Remote Similarity	0.6124	NPC230276
Remote Similarity	0.6121	NPC316091
Remote Similarity	0.612	NPC24869
Remote Similarity	0.6119	NPC80759
Remote Similarity	0.6119	NPC79402
Remote Similarity	0.6117	NPC256935
Remote Similarity	0.6117	NPC474311
Remote Similarity	0.6114	NPC476444
Remote Similarity	0.6114	NPC10764
Remote Similarity	0.6108	NPC470561
Remote Similarity	0.6108	NPC473696
Remote Similarity	0.6108	NPC474096
Remote Similarity	0.6101	NPC469689
Remote Similarity	0.6101	NPC471031
Remote Similarity	0.61	NPC221864
Remote Similarity	0.6099	NPC71610
Remote Similarity	0.6098	NPC311679
Remote Similarity	0.6098	NPC28669
Remote Similarity	0.6096	NPC202225
Remote Similarity	0.6094	NPC193555
Remote Similarity	0.6089	NPC284495
Remote Similarity	0.6087	NPC89769
Remote Similarity	0.6087	NPC126859
Remote Similarity	0.6087	NPC259665
Remote Similarity	0.6085	NPC305060
Remote Similarity	0.6082	NPC471683
Remote Similarity	0.6078	NPC470563
Remote Similarity	0.6077	NPC474766
Remote Similarity	0.6077	NPC40496
Remote Similarity	0.6077	NPC119068
Remote Similarity	0.6075	NPC246693
Remote Similarity	0.6075	NPC242358
Remote Similarity	0.6075	NPC110609
Remote Similarity	0.6071	NPC473719
Remote Similarity	0.607	NPC230956
Remote Similarity	0.607	NPC197326
Remote Similarity	0.607	NPC119649
Remote Similarity	0.607	NPC271388
Remote Similarity	0.607	NPC235143
Remote Similarity	0.607	NPC205255
Remote Similarity	0.6066	NPC306240
Remote Similarity	0.6066	NPC471530
Remote Similarity	0.6064	NPC283088
Remote Similarity	0.6062	NPC478164
Remote Similarity	0.6062	NPC471682
Remote Similarity	0.6059	NPC472157
Remote Similarity	0.6059	NPC472405
Remote Similarity	0.6059	NPC298401
Remote Similarity	0.6053	NPC13715
Remote Similarity	0.6051	NPC143685
Remote Similarity	0.6051	NPC285122
Remote Similarity	0.6049	NPC173352
Remote Similarity	0.6049	NPC58653
Remote Similarity	0.6048	NPC257269
Remote Similarity	0.6045	NPC97086
Remote Similarity	0.6042	NPC91019
Remote Similarity	0.6042	NPC106519
Remote Similarity	0.6041	NPC477567
Remote Similarity	0.6041	NPC477566
Remote Similarity	0.604	NPC15506
Remote Similarity	0.6039	NPC192135
Remote Similarity	0.6039	NPC477020
Remote Similarity	0.6039	NPC66341
Remote Similarity	0.6038	NPC214629
Remote Similarity	0.6036	NPC126211
Remote Similarity	0.6033	NPC124802
Remote Similarity	0.6031	NPC471906
Remote Similarity	0.6031	NPC79627
Remote Similarity	0.6029	NPC188120
Remote Similarity	0.6029	NPC245122
Remote Similarity	0.6029	NPC53146
Remote Similarity	0.6029	NPC286790
Remote Similarity	0.6025	NPC3921
Remote Similarity	0.6022	NPC135062
Remote Similarity	0.6022	NPC198014
Remote Similarity	0.6022	NPC273683
Remote Similarity	0.6022	NPC476847
Remote Similarity	0.6022	NPC471187
Remote Similarity	0.602	NPC477569
Remote Similarity	0.6019	NPC474061
Remote Similarity	0.6011	NPC3224
Remote Similarity	0.6011	NPC109580
Remote Similarity	0.6011	NPC1991
Remote Similarity	0.601	NPC470565
Remote Similarity	0.601	NPC474961
Remote Similarity	0.601	NPC474004
Remote Similarity	0.601	NPC257644
Remote Similarity	0.6009	NPC157958
Remote Similarity	0.6	NPC126676
Remote Similarity	0.6	NPC96160
Remote Similarity	0.6	NPC478160
Remote Similarity	0.6	NPC154696
Remote Similarity	0.6	NPC4331
Remote Similarity	0.6	NPC245923
Remote Similarity	0.6	NPC474507
Remote Similarity	0.6	NPC303910
Remote Similarity	0.6	NPC99723
Remote Similarity	0.6	NPC469671
Remote Similarity	0.6	NPC471452
Remote Similarity	0.6	NPC170055
Remote Similarity	0.599	NPC94781
Remote Similarity	0.599	NPC169452
Remote Similarity	0.599	NPC181560
Remote Similarity	0.599	NPC142846
Remote Similarity	0.599	NPC474637
Remote Similarity	0.599	NPC472032
Remote Similarity	0.599	NPC112816
Remote Similarity	0.599	NPC226428
Remote Similarity	0.5989	NPC58685
Remote Similarity	0.5989	NPC181334
Remote Similarity	0.5982	NPC106840
Remote Similarity	0.5982	NPC94687

Drug Structure

NPD5543 OpenBabel08211708292D 42 45 0 0 1 0 0 0 0 0999 V2000 3.2333 -2.1591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 -2.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0832 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0832 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3888 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 -0.9783 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.9783 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2360 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2360 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6944 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 -1.4674 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5416 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6944 -0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 -1.4674 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2360 -2.4457 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -3.3888 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 -2.4457 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.2360 -1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2360 1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5416 1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 -1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 1.4674 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6378 -1.8418 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2360 0.4891 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2360 -2.4457 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0832 1.9565 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 1.9565 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3888 1.9565 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5101 -2.8116 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 2.4457 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 25 1 0 0 0 0 7 27 1 0 0 0 0 8 12 1 0 0 0 0 8 22 1 1 0 0 0 9 16 1 0 0 0 0 9 23 1 1 0 0 0 10 15 2 0 0 0 0 10 24 1 0 0 0 0 11 13 2 0 0 0 0 11 28 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 14 20 1 0 0 0 0 14 21 2 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 16 26 1 6 0 0 0 17 29 1 0 0 0 0 18 30 2 0 0 0 0 19 23 1 0 0 0 0 19 31 2 0 0 0 0 20 23 1 0 0 0 0 20 32 2 0 0 0 0 21 25 1 0 0 0 0 21 33 1 0 0 0 0 22 1 1 6 0 0 0 22 34 1 0 0 0 0 23 35 1 6 0 0 0 25 36 1 0 0 0 0 27 37 1 0 0 0 0 28 38 1 0 0 0 0 29 39 1 0 0 0 0 33 40 1 0 0 0 0 34 41 1 0 0 0 0 35 42 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000882
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	5464321
ChEBI
CAS Number

Drug Properties

Molecular Weight	508.12
ALogP	-2.7765
MLogP	2.67
XLogP	0.975
HDA	10
HBD	7
Rotatable Bonds	13
TPSA	187.86
RO5 Violation	1