NPASS drugs

Drug Information

Drug ID:	NPD4388
Drug Name:
Molecular Formula:	C21H21ClN2O8
Canonical SMILES:	CN(C1C(=O)/C(=C(O)/N)/C(=O)C2(C1CC1C(=C(O)c3c(C1O)c(Cl)ccc3O)C2=O)O)C
Standard InCHI:	InChI=1S/C21H21ClN2O8/c1-24(2)14-7-5-6-10(16(27)12-9(25)4-3-8(22)11(12)15(6)26)18(29)21(7,32)19(30)13(17(14)28)20(23)31/h3-4,6-7,14-15,25-27,31-32H,5,23H2,1-2H3/b20-13+
Standard InCHIKey:	HXPZLYXFFSKHJA-DEDYPNTBSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD4388

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	219
0.1-0.2	1110
0.2-0.3	3092
0.3-0.4	8692
0.4-0.5	7427
0.5-0.6	10052
0.6-0.7	293
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	0.8196	NPC96730
Intermediate Similarity	0.799	NPC39528
Intermediate Similarity	0.7436	NPC295531
Intermediate Similarity	0.7231	NPC469973
Intermediate Similarity	0.7179	NPC291305
Remote Similarity	0.6798	NPC329790
Remote Similarity	0.6667	NPC68967
Remote Similarity	0.6635	NPC264938
Remote Similarity	0.6606	NPC313582
Remote Similarity	0.6543	NPC2672
Remote Similarity	0.6533	NPC12890
Remote Similarity	0.6526	NPC316164
Remote Similarity	0.6515	NPC314693
Remote Similarity	0.6465	NPC101207
Remote Similarity	0.6453	NPC474857
Remote Similarity	0.6452	NPC314596
Remote Similarity	0.6447	NPC470559
Remote Similarity	0.6439	NPC298339
Remote Similarity	0.6432	NPC42286
Remote Similarity	0.6432	NPC317727
Remote Similarity	0.6429	NPC472623
Remote Similarity	0.6429	NPC474861
Remote Similarity	0.6406	NPC314946
Remote Similarity	0.6404	NPC87985
Remote Similarity	0.6402	NPC313274
Remote Similarity	0.64	NPC470081
Remote Similarity	0.6378	NPC314257
Remote Similarity	0.6359	NPC314941
Remote Similarity	0.6349	NPC469520
Remote Similarity	0.6349	NPC85310
Remote Similarity	0.6347	NPC315889
Remote Similarity	0.6345	NPC280497
Remote Similarity	0.6344	NPC475957
Remote Similarity	0.6338	NPC66909
Remote Similarity	0.6333	NPC191606
Remote Similarity	0.6327	NPC472211
Remote Similarity	0.6327	NPC218870
Remote Similarity	0.6327	NPC182921
Remote Similarity	0.6327	NPC474824
Remote Similarity	0.6327	NPC470408
Remote Similarity	0.6326	NPC314738
Remote Similarity	0.6326	NPC109403
Remote Similarity	0.6326	NPC313541
Remote Similarity	0.6326	NPC261012
Remote Similarity	0.6313	NPC475780
Remote Similarity	0.6313	NPC472404
Remote Similarity	0.6311	NPC264922
Remote Similarity	0.6296	NPC151470
Remote Similarity	0.6296	NPC254045
Remote Similarity	0.6296	NPC64576
Remote Similarity	0.6296	NPC201055
Remote Similarity	0.6287	NPC163924
Remote Similarity	0.6287	NPC54661
Remote Similarity	0.6282	NPC328287
Remote Similarity	0.6278	NPC315253
Remote Similarity	0.6274	NPC316091
Remote Similarity	0.6269	NPC470561
Remote Similarity	0.6269	NPC473696
Remote Similarity	0.6269	NPC195392
Remote Similarity	0.6269	NPC474096
Remote Similarity	0.6267	NPC244191
Remote Similarity	0.6263	NPC470564
Remote Similarity	0.6262	NPC279665
Remote Similarity	0.6257	NPC238108
Remote Similarity	0.6257	NPC305060
Remote Similarity	0.6256	NPC315520
Remote Similarity	0.6256	NPC131078
Remote Similarity	0.6256	NPC301846
Remote Similarity	0.6256	NPC28669
Remote Similarity	0.625	NPC284495
Remote Similarity	0.625	NPC110609
Remote Similarity	0.625	NPC242358
Remote Similarity	0.625	NPC246693
Remote Similarity	0.6244	NPC329969
Remote Similarity	0.6238	NPC470563
Remote Similarity	0.6237	NPC473719
Remote Similarity	0.6233	NPC316412
Remote Similarity	0.6233	NPC315351
Remote Similarity	0.623	NPC478164
Remote Similarity	0.6226	NPC196231
Remote Similarity	0.6219	NPC472405
Remote Similarity	0.6219	NPC298401
Remote Similarity	0.6218	NPC285122
Remote Similarity	0.6218	NPC143685
Remote Similarity	0.6211	NPC91019
Remote Similarity	0.6211	NPC106519
Remote Similarity	0.6211	NPC297322
Remote Similarity	0.6207	NPC58653
Remote Similarity	0.6207	NPC173352
Remote Similarity	0.6203	NPC272268
Remote Similarity	0.62	NPC15506
Remote Similarity	0.6198	NPC471906
Remote Similarity	0.6198	NPC79627
Remote Similarity	0.6196	NPC476847
Remote Similarity	0.6195	NPC108948
Remote Similarity	0.6195	NPC184518
Remote Similarity	0.6193	NPC97086
Remote Similarity	0.619	NPC151292
Remote Similarity	0.619	NPC214629
Remote Similarity	0.6188	NPC71610
Remote Similarity	0.6188	NPC245122
Remote Similarity	0.6184	NPC73555
Remote Similarity	0.6183	NPC202225
Remote Similarity	0.6178	NPC474961
Remote Similarity	0.6176	NPC474061
Remote Similarity	0.6167	NPC181334
Remote Similarity	0.6166	NPC170055
Remote Similarity	0.6166	NPC478160
Remote Similarity	0.6165	NPC277865
Remote Similarity	0.6165	NPC474004
Remote Similarity	0.6157	NPC293624
Remote Similarity	0.6154	NPC142846
Remote Similarity	0.6154	NPC112816
Remote Similarity	0.6154	NPC94781
Remote Similarity	0.6146	NPC3732
Remote Similarity	0.6146	NPC472032
Remote Similarity	0.6142	NPC477276
Remote Similarity	0.6139	NPC255607
Remote Similarity	0.6139	NPC3375
Remote Similarity	0.6135	NPC470560
Remote Similarity	0.6134	NPC314437
Remote Similarity	0.6134	NPC136878
Remote Similarity	0.6132	NPC51047
Remote Similarity	0.6131	NPC68727
Remote Similarity	0.6131	NPC474501
Remote Similarity	0.6129	NPC314048
Remote Similarity	0.6129	NPC115458
Remote Similarity	0.6129	NPC78307
Remote Similarity	0.6127	NPC73544
Remote Similarity	0.6126	NPC476495
Remote Similarity	0.6126	NPC94687
Remote Similarity	0.6126	NPC106840
Remote Similarity	0.6124	NPC115906
Remote Similarity	0.6122	NPC44378
Remote Similarity	0.6122	NPC280753
Remote Similarity	0.6122	NPC472939
Remote Similarity	0.6122	NPC477221
Remote Similarity	0.6121	NPC313386
Remote Similarity	0.612	NPC24869
Remote Similarity	0.6119	NPC67346
Remote Similarity	0.6119	NPC232533
Remote Similarity	0.6119	NPC80759
Remote Similarity	0.6119	NPC79402
Remote Similarity	0.6117	NPC256935
Remote Similarity	0.6117	NPC474311
Remote Similarity	0.6114	NPC84568
Remote Similarity	0.6114	NPC476444
Remote Similarity	0.6114	NPC48130
Remote Similarity	0.6114	NPC10764
Remote Similarity	0.6114	NPC300684
Remote Similarity	0.6114	NPC218866
Remote Similarity	0.6114	NPC29932
Remote Similarity	0.6111	NPC198014
Remote Similarity	0.6111	NPC471187
Remote Similarity	0.6111	NPC478220
Remote Similarity	0.6111	NPC316461
Remote Similarity	0.6108	NPC315772
Remote Similarity	0.6103	NPC470103
Remote Similarity	0.6103	NPC52161
Remote Similarity	0.6103	NPC5568
Remote Similarity	0.6103	NPC162751
Remote Similarity	0.61	NPC221864
Remote Similarity	0.6099	NPC476496
Remote Similarity	0.6098	NPC311679
Remote Similarity	0.6098	NPC227778
Remote Similarity	0.6094	NPC248068
Remote Similarity	0.6094	NPC193555
Remote Similarity	0.6094	NPC135524
Remote Similarity	0.6094	NPC137649
Remote Similarity	0.6093	NPC289223
Remote Similarity	0.6092	NPC3921
Remote Similarity	0.6091	NPC225854
Remote Similarity	0.6089	NPC31936
Remote Similarity	0.6087	NPC478021
Remote Similarity	0.6087	NPC89769
Remote Similarity	0.6087	NPC470562
Remote Similarity	0.6087	NPC126859
Remote Similarity	0.6087	NPC259665
Remote Similarity	0.6085	NPC150712
Remote Similarity	0.6085	NPC162694
Remote Similarity	0.6082	NPC471683
Remote Similarity	0.6081	NPC326895
Remote Similarity	0.6078	NPC89831
Remote Similarity	0.6077	NPC471684
Remote Similarity	0.6077	NPC474766
Remote Similarity	0.6077	NPC74507
Remote Similarity	0.6077	NPC234890
Remote Similarity	0.6075	NPC165612
Remote Similarity	0.6071	NPC290695
Remote Similarity	0.6071	NPC106524
Remote Similarity	0.607	NPC230956
Remote Similarity	0.607	NPC197326
Remote Similarity	0.607	NPC119649
Remote Similarity	0.607	NPC271388
Remote Similarity	0.607	NPC29552
Remote Similarity	0.607	NPC235143
Remote Similarity	0.607	NPC205255
Remote Similarity	0.6068	NPC477115
Remote Similarity	0.6066	NPC262936
Remote Similarity	0.6066	NPC306240

Drug Structure

NPD4388 OpenBabel08211705262D 39 42 0 0 1 0 0 0 0 0999 V2000 -1.6918 -2.9302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0753 -0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0753 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 -0.9767 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -0.9767 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.2294 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2294 0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3835 -0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3835 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 -1.4651 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5377 -1.4651 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5377 0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 -0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5377 0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.2294 -2.4419 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -2.5377 1.4651 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 -2.4419 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.2294 1.4651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 -2.4419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 1.4651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5377 -1.4651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 1.4651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 1.4651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3835 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 1.9535 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3835 1.9535 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0753 1.9535 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3835 -2.9302 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3835 1.9535 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2294 0.4884 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 2.4419 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 24 1 0 0 0 0 3 4 2 0 0 0 0 3 8 1 0 0 0 0 4 9 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 10 1 0 0 0 0 6 15 1 0 0 0 0 7 14 1 0 0 0 0 7 21 1 0 0 0 0 8 11 2 0 0 0 0 8 22 1 0 0 0 0 9 12 2 0 0 0 0 9 25 1 0 0 0 0 10 16 2 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 13 19 1 0 0 0 0 13 20 2 0 0 0 0 14 17 1 0 0 0 0 14 24 1 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 28 2 0 0 0 0 18 21 1 0 0 0 0 18 29 2 0 0 0 0 19 21 1 0 0 0 0 19 30 2 0 0 0 0 20 23 1 0 0 0 0 20 31 1 0 0 0 0 21 32 1 0 0 0 0 23 33 1 0 0 0 0 23 34 1 0 0 0 0 25 35 1 0 0 0 0 26 36 1 0 0 0 0 27 37 1 0 0 0 0 31 38 1 0 0 0 0 32 39 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000402
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	5367858
ChEBI
CAS Number

Drug Properties

Molecular Weight	464.10
ALogP	-3.128
MLogP	2.56
XLogP	0.667
HDA	9
HBD	6
Rotatable Bonds	10
TPSA	181.62
RO5 Violation	1