NPASS drugs

Drug Information

Drug ID:	NPD6166
Drug Name:	Silibinin
Molecular Formula:	C25H22O10
Canonical SMILES:	OCC1Oc2ccc(cc2OC1c1ccc(c(c1)OC)O)C1Oc2cc(O)cc(c2C(=O)C1O)O
Standard InCHI:	"InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3"
Standard InCHIKey:	SEBFKMXJBCUCAI-UHFFFAOYSA-N
Max Developmental Stage:	Phase 2
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD6166

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	110905
0.1-0.2	84670
0.2-0.3	13603
0.3-0.4	2115
0.4-0.5	337
0.5-0.6	63
0.6-0.7	17
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	22

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	NPC162872
High Similarity	1.0	NPC36916
High Similarity	1.0	NPC36
High Similarity	1.0	NPC71708
High Similarity	1.0	NPC7154
High Similarity	1.0	NPC125039
High Similarity	1.0	NPC7688
High Similarity	1.0	NPC324704
High Similarity	1.0	NPC247525
High Similarity	1.0	NPC599795
High Similarity	1.0	NPC608275
High Similarity	1.0	NPC611648
High Similarity	0.9545	NPC138688
High Similarity	0.9545	NPC72787
High Similarity	0.9545	NPC217795
High Similarity	0.9545	NPC289803
High Similarity	0.9545	NPC237093
High Similarity	0.9545	NPC58223
High Similarity	0.9545	NPC260317
High Similarity	0.9545	NPC559551
High Similarity	0.9545	NPC600445
High Similarity	0.9545	NPC603636
Intermediate Similarity	0.7887	NPC159720
Intermediate Similarity	0.7656	NPC326037
Intermediate Similarity	0.7656	NPC13858
Intermediate Similarity	0.7534	NPC260257
Intermediate Similarity	0.72	NPC45000
Remote Similarity	0.641	NPC232227
Remote Similarity	0.641	NPC215647
Remote Similarity	0.641	NPC527364
Remote Similarity	0.6154	NPC587989
Remote Similarity	0.6154	NPC606364
Remote Similarity	0.6087	NPC320825
Remote Similarity	0.6087	NPC541452
Remote Similarity	0.6049	NPC56229
Remote Similarity	0.6049	NPC279209
Remote Similarity	0.6049	NPC102277
Remote Similarity	0.6049	NPC479117
Remote Similarity	0.6049	NPC600844
Remote Similarity	0.6029	NPC200477
Remote Similarity	0.6029	NPC551105
Remote Similarity	0.6027	NPC589652
Remote Similarity	0.6	NPC242115
Remote Similarity	0.6	NPC558922
Remote Similarity	0.5915	NPC528602
Remote Similarity	0.5915	NPC537306
Remote Similarity	0.5915	NPC565558
Remote Similarity	0.5882	NPC44721
Remote Similarity	0.5882	NPC211466
Remote Similarity	0.5882	NPC566726
Remote Similarity	0.5882	NPC605332
Remote Similarity	0.5857	NPC52530
Remote Similarity	0.5857	NPC502911
Remote Similarity	0.5821	NPC62290
Remote Similarity	0.5821	NPC142731
Remote Similarity	0.5821	NPC326506
Remote Similarity	0.5821	NPC104616
Remote Similarity	0.5821	NPC117897
Remote Similarity	0.5797	NPC36835
Remote Similarity	0.5797	NPC246162
Remote Similarity	0.5797	NPC9743
Remote Similarity	0.5797	NPC260491
Remote Similarity	0.5797	NPC61506
Remote Similarity	0.5797	NPC233443
Remote Similarity	0.5797	NPC240476
Remote Similarity	0.5753	NPC5851
Remote Similarity	0.5753	NPC560224
Remote Similarity	0.56	NPC516806
Remote Similarity	0.5571	NPC97094
Remote Similarity	0.5571	NPC250922
Remote Similarity	0.5529	NPC158188
Remote Similarity	0.5507	NPC162806
Remote Similarity	0.5467	NPC86030
Remote Similarity	0.5375	NPC80078
Remote Similarity	0.5366	NPC190870
Remote Similarity	0.5366	NPC537841
Remote Similarity	0.5362	NPC74416
Remote Similarity	0.5362	NPC4152
Remote Similarity	0.5362	NPC536567
Remote Similarity	0.5357	NPC100400
Remote Similarity	0.5342	NPC140925
Remote Similarity	0.5342	NPC236637
Remote Similarity	0.5342	NPC514723
Remote Similarity	0.5326	NPC551670
Remote Similarity	0.5286	NPC325509
Remote Similarity	0.5286	NPC203467
Remote Similarity	0.5286	NPC19721
Remote Similarity	0.5286	NPC497331
Remote Similarity	0.5286	NPC599899
Remote Similarity	0.525	NPC71106
Remote Similarity	0.525	NPC305454
Remote Similarity	0.5238	NPC125665
Remote Similarity	0.5238	NPC545569
Remote Similarity	0.5217	NPC21835
Remote Similarity	0.5205	NPC16435
Remote Similarity	0.5205	NPC294952
Remote Similarity	0.5205	NPC517460
Remote Similarity	0.5205	NPC590295
Remote Similarity	0.5205	NPC595409
Remote Similarity	0.5176	NPC519695
Remote Similarity	0.5158	NPC567339
Remote Similarity	0.5143	NPC6501
Remote Similarity	0.5143	NPC279417
Remote Similarity	0.5143	NPC49130
Remote Similarity	0.506	NPC280211
Remote Similarity	0.5057	NPC224390
Remote Similarity	0.5057	NPC592473

Drug Structure

NPD6166 OpenBabel08211709092D 40 44 0 0 1 0 0 0 0 0999 V2000 -8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 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 -6.9282 0.0000 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 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 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -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 -5.1962 0.0000 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 -6.0622 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -2.0000 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 -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 -8.6603 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 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 -5.1962 3.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -3.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -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 32 1 0 0 0 0 2 4 2 0 0 0 0 2 11 1 0 0 0 0 3 5 2 0 0 0 0 3 12 1 0 0 0 0 4 14 1 0 0 0 0 5 16 1 0 0 0 0 6 11 2 0 0 0 0 6 17 1 0 0 0 0 7 12 2 0 0 0 0 7 18 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 9 19 2 0 0 0 0 10 20 1 0 0 0 0 10 26 1 0 0 0 0 11 24 1 0 0 0 0 12 25 1 0 0 0 0 13 27 1 0 0 0 0 14 17 2 0 0 0 0 14 28 1 0 0 0 0 15 21 2 0 0 0 0 15 29 1 0 0 0 0 16 18 2 0 0 0 0 16 33 1 0 0 0 0 17 32 1 0 0 0 0 18 34 1 0 0 0 0 19 21 1 0 0 0 0 19 35 1 0 0 0 0 20 24 1 0 0 0 0 20 33 1 0 0 0 0 21 22 1 0 0 0 0 22 23 1 0 0 0 0 22 30 2 0 0 0 0 23 25 1 0 0 0 0 23 31 1 0 0 0 0 24 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 28 38 1 0 0 0 0 29 39 1 0 0 0 0 31 40 1 0 0 0 0 M END $$$$

External Identifiers

TTD
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	0
ChEBI
CAS Number

Drug Properties

Molecular Weight	482.12
ALogP	-3.3761
MLogP	3.11
XLogP	0.66
HDA	3
HBD	5
Rotatable Bonds	10
TPSA	155.14
RO5 Violation	0