NPASS drugs

Drug Information

Drug ID:	NPD4381
Drug Name:
Molecular Formula:	C21H20O9
Canonical SMILES:	OCC1OC(Oc2ccc3c(c2)occ(c3=O)c2ccc(cc2)O)C(C(C1O)O)O
Standard InCHI:	"InChI=1S/C21H20O9/c22-8-16-18(25)19(26)20(27)21(30-16)29-12-5-6-13-15(7-12)28-9-14(17(13)24)10-1-3-11(23)4-2-10/h1-7,9,16,18-23,25-27H,8H2"
Standard InCHIKey:	KYQZWONCHDNPDP-UHFFFAOYSA-N
Max Developmental Stage:	Clinical (unspecified phase)
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD4381

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.
Tanimoto coefficient is calculated based on PubChem 881-bit substructure fingerprints.

Range	Similarity Score Range
0-0.1	83123
0.1-0.2	105820
0.2-0.3	15131
0.3-0.4	5370
0.4-0.5	1817
0.5-0.6	25
0.6-0.7	110
0.7-0.8	46
0.8-0.85	9
0.85-0.9	6
0.9-0.95	0
0.95-1	4

Similar Natural Products

High Similarity: Tc>=0.85; Intermediate Similarity: 0.7 <= Tc < 0.85; Remote Similarity: 0.5 <= Tc < 0.7

Similarity Level	Similarity Score	Natural Product ID
High Similarity	1.0	NPC321992
High Similarity	1.0	NPC161749
High Similarity	1.0	NPC90489
High Similarity	1.0	NPC602657
High Similarity	0.8955	NPC542929
High Similarity	0.8714	NPC78192
High Similarity	0.8529	NPC310109
High Similarity	0.8529	NPC323243
High Similarity	0.8529	NPC496988
High Similarity	0.8529	NPC522866
Intermediate Similarity	0.8429	NPC211014
Intermediate Similarity	0.8286	NPC45165
Intermediate Similarity	0.8286	NPC225778
Intermediate Similarity	0.8286	NPC51862
Intermediate Similarity	0.8286	NPC198030
Intermediate Similarity	0.8286	NPC526144
Intermediate Similarity	0.8286	NPC603801
Intermediate Similarity	0.8133	NPC233465
Intermediate Similarity	0.8028	NPC279790
Intermediate Similarity	0.7867	NPC184368
Intermediate Similarity	0.7867	NPC319449
Intermediate Similarity	0.7867	NPC229729
Intermediate Similarity	0.7867	NPC54472
Intermediate Similarity	0.7867	NPC533134
Intermediate Similarity	0.7867	NPC573804
Intermediate Similarity	0.7838	NPC518822
Intermediate Similarity	0.7808	NPC105511
Intermediate Similarity	0.7808	NPC74119
Intermediate Similarity	0.7808	NPC495614
Intermediate Similarity	0.7763	NPC155999
Intermediate Similarity	0.7763	NPC490009
Intermediate Similarity	0.7763	NPC492682
Intermediate Similarity	0.7763	NPC493301
Intermediate Similarity	0.7763	NPC502201
Intermediate Similarity	0.7703	NPC572798
Intermediate Similarity	0.7568	NPC120612
Intermediate Similarity	0.7568	NPC197896
Intermediate Similarity	0.7568	NPC192875
Intermediate Similarity	0.7568	NPC258035
Intermediate Similarity	0.7568	NPC313163
Intermediate Similarity	0.7568	NPC203398
Intermediate Similarity	0.7568	NPC518521
Intermediate Similarity	0.7568	NPC541435
Intermediate Similarity	0.7568	NPC603330
Intermediate Similarity	0.7403	NPC544874
Intermediate Similarity	0.7403	NPC579692
Intermediate Similarity	0.7403	NPC601607
Intermediate Similarity	0.7368	NPC100720
Intermediate Similarity	0.7368	NPC493199
Intermediate Similarity	0.7368	NPC547845
Intermediate Similarity	0.7368	NPC566722
Intermediate Similarity	0.7342	NPC502176
Intermediate Similarity	0.7284	NPC78509
Intermediate Similarity	0.7237	NPC176244
Intermediate Similarity	0.7195	NPC492530
Intermediate Similarity	0.7143	NPC205076
Intermediate Similarity	0.7143	NPC265376
Intermediate Similarity	0.7143	NPC514050
Intermediate Similarity	0.7143	NPC518678
Intermediate Similarity	0.7143	NPC564926
Intermediate Similarity	0.7123	NPC25547
Intermediate Similarity	0.7105	NPC319857
Intermediate Similarity	0.7024	NPC95495
Intermediate Similarity	0.7024	NPC490398
Intermediate Similarity	0.7024	NPC565903
Remote Similarity	0.6951	NPC580796
Remote Similarity	0.6914	NPC520385
Remote Similarity	0.6883	NPC50504
Remote Similarity	0.6883	NPC523850
Remote Similarity	0.6883	NPC537746
Remote Similarity	0.6883	NPC590770
Remote Similarity	0.6842	NPC135345
Remote Similarity	0.6842	NPC541685
Remote Similarity	0.6842	NPC579049
Remote Similarity	0.6835	NPC557712
Remote Similarity	0.6753	NPC79765
Remote Similarity	0.6753	NPC501203
Remote Similarity	0.6753	NPC517748
Remote Similarity	0.6753	NPC532607
Remote Similarity	0.6753	NPC546067
Remote Similarity	0.6753	NPC591045
Remote Similarity	0.6709	NPC506272
Remote Similarity	0.6709	NPC570977
Remote Similarity	0.6705	NPC540669
Remote Similarity	0.6667	NPC500587
Remote Similarity	0.6667	NPC587878
Remote Similarity	0.6588	NPC523823
Remote Similarity	0.6582	NPC281606
Remote Similarity	0.6582	NPC116841
Remote Similarity	0.6582	NPC179285
Remote Similarity	0.6582	NPC13473
Remote Similarity	0.6582	NPC73511
Remote Similarity	0.6582	NPC493096
Remote Similarity	0.6582	NPC511771
Remote Similarity	0.6582	NPC514681
Remote Similarity	0.6582	NPC514905
Remote Similarity	0.6582	NPC520103
Remote Similarity	0.6582	NPC549455
Remote Similarity	0.6582	NPC583322
Remote Similarity	0.6538	NPC259070
Remote Similarity	0.65	NPC200663
Remote Similarity	0.65	NPC305032
Remote Similarity	0.65	NPC494056
Remote Similarity	0.65	NPC547166
Remote Similarity	0.65	NPC548860
Remote Similarity	0.65	NPC568005
Remote Similarity	0.65	NPC579730
Remote Similarity	0.6471	NPC181124
Remote Similarity	0.6471	NPC609129
Remote Similarity	0.6456	NPC156457
Remote Similarity	0.6456	NPC213182
Remote Similarity	0.6456	NPC517607
Remote Similarity	0.6456	NPC546472
Remote Similarity	0.642	NPC166057
Remote Similarity	0.642	NPC202431
Remote Similarity	0.642	NPC501224
Remote Similarity	0.642	NPC510837
Remote Similarity	0.642	NPC596414
Remote Similarity	0.6395	NPC479405
Remote Similarity	0.6364	NPC552807
Remote Similarity	0.6341	NPC567036
Remote Similarity	0.6329	NPC348541
Remote Similarity	0.6329	NPC160844
Remote Similarity	0.6329	NPC584493
Remote Similarity	0.6322	NPC479404
Remote Similarity	0.6279	NPC567187
Remote Similarity	0.6265	NPC526968
Remote Similarity	0.6265	NPC572364
Remote Similarity	0.625	NPC517449
Remote Similarity	0.625	NPC548276
Remote Similarity	0.625	NPC576678
Remote Similarity	0.625	NPC603782
Remote Similarity	0.622	NPC270867
Remote Similarity	0.622	NPC80140
Remote Similarity	0.622	NPC493554
Remote Similarity	0.622	NPC560917
Remote Similarity	0.622	NPC610600
Remote Similarity	0.619	NPC9430
Remote Similarity	0.619	NPC479407
Remote Similarity	0.619	NPC525406
Remote Similarity	0.619	NPC546811
Remote Similarity	0.6173	NPC472526
Remote Similarity	0.6173	NPC100305
Remote Similarity	0.6173	NPC520527
Remote Similarity	0.6173	NPC551829
Remote Similarity	0.6163	NPC158558
Remote Similarity	0.6163	NPC272405
Remote Similarity	0.6163	NPC553291
Remote Similarity	0.6154	NPC231194
Remote Similarity	0.6118	NPC224368
Remote Similarity	0.6118	NPC269710
Remote Similarity	0.6118	NPC61989
Remote Similarity	0.6118	NPC493812
Remote Similarity	0.6118	NPC587074
Remote Similarity	0.6092	NPC91213
Remote Similarity	0.6092	NPC79836
Remote Similarity	0.6092	NPC31184
Remote Similarity	0.6092	NPC539653
Remote Similarity	0.6071	NPC33117
Remote Similarity	0.6071	NPC479406
Remote Similarity	0.6071	NPC74682
Remote Similarity	0.6071	NPC492918
Remote Similarity	0.6071	NPC531877
Remote Similarity	0.6067	NPC552787
Remote Similarity	0.6067	NPC554295
Remote Similarity	0.6049	NPC168822
Remote Similarity	0.6049	NPC234739
Remote Similarity	0.6049	NPC550054
Remote Similarity	0.6049	NPC573661
Remote Similarity	0.6049	NPC579490
Remote Similarity	0.6049	NPC594301
Remote Similarity	0.6024	NPC543521
Remote Similarity	0.6	NPC19096
Remote Similarity	0.6	NPC48773
Remote Similarity	0.6	NPC510480
Remote Similarity	0.5977	NPC170258
Remote Similarity	0.5977	NPC305741
Remote Similarity	0.5977	NPC20006
Remote Similarity	0.5977	NPC507810
Remote Similarity	0.5977	NPC517231
Remote Similarity	0.5977	NPC597935
Remote Similarity	0.5976	NPC596605
Remote Similarity	0.5957	NPC45908
Remote Similarity	0.5955	NPC221398
Remote Similarity	0.5955	NPC523496
Remote Similarity	0.5952	NPC564549
Remote Similarity	0.5952	NPC568320
Remote Similarity	0.5934	NPC51326
Remote Similarity	0.593	NPC594792
Remote Similarity	0.5926	NPC498673
Remote Similarity	0.5909	NPC103728
Remote Similarity	0.5909	NPC530744
Remote Similarity	0.5904	NPC288426
Remote Similarity	0.5904	NPC521157
Remote Similarity	0.5904	NPC586351
Remote Similarity	0.5882	NPC472528
Remote Similarity	0.5882	NPC307518
Remote Similarity	0.5882	NPC63391
Remote Similarity	0.5882	NPC525582
Remote Similarity	0.5875	NPC98304

Drug Structure

NPD4381 OpenBabel08211705262D 35 38 0 0 1 0 0 0 0 0999 V2000 6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 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 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 3 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 8.6603 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 6.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 10 2 0 0 0 0 2 4 2 0 0 0 0 2 10 1 0 0 0 0 3 11 2 0 0 0 0 4 11 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 12 2 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 8 22 1 0 0 0 0 9 14 2 0 0 0 0 9 28 1 0 0 0 0 10 14 1 0 0 0 0 11 23 1 0 0 0 0 12 29 1 0 0 0 0 13 15 2 0 0 0 0 13 17 1 0 0 0 0 14 17 1 0 0 0 0 15 28 1 0 0 0 0 16 18 1 0 0 0 0 16 30 1 0 0 0 0 17 24 2 0 0 0 0 18 19 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 27 1 0 0 0 0 21 29 1 0 0 0 0 21 30 1 0 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 25 33 1 0 0 0 0 26 34 1 0 0 0 0 27 35 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DNC002527
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	4183640
ChEBI
CAS Number

Drug Properties

Molecular Weight	416.11
ALogP	-3.3342
MLogP	2.78
XLogP	1.367
HDA	6
HBD	5
Rotatable Bonds	9
TPSA	145.91
RO5 Violation	0