IMPPAT Phytochemical information: 
Silibinin
Silibinin
Summary

SMILES: OC[C@H]1Oc2ccc(cc2O[C@@H]1c1ccc(c(c1)OC)O)[C@H]1Oc2cc(O)cc(c2C(=O)[C@@H]1O)O
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/t20-,23+,24-,25-/m1/s1
InChIKey: SEBFKMXJBCUCAI-HKTJVKLFSA-N
DeepSMILES: OC[C@H]Occcccc6O[C@@H]%10cccccc6)OC)))O)))))))))[C@H]OcccO)ccc6C=O)[C@@H]%10O))))O
Scaffold Graph/Node/Bond level: O=C1CC(c2ccc3c(c2)OC(c2ccccc2)CO3)Oc2ccccc21
Scaffold Graph/Node level: OC1CC(C2CCC3OCC(C4CCCCC4)OC3C2)OC2CCCCC12
Scaffold Graph level: CC1CC(C2CCC3CCC(C4CCCCC4)CC3C2)CC2CCCCC12
Functional groups: CO; cC(C)=O; cO; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Flavonolignans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans|Flavonoids
NP Classifier Class: Dihydroflavonols|Flavonolignans
Synonymous chemical names:
silibinin, silybin, silymarin (flavanol lignin mixture)
External chemical identifiers:
CID:31553; ChEMBL:CHEMBL431701; ChEBI:9144; ZINC:ZINC000002033589; FDASRS:33X338MNE4; SureChEMBL:SCHEMBL324884; MolPort-001-741-606
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Silibinin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 482.44
Log P RDKit 2.36
Topological polar surface area (Å2) RDKit 155.14
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 25
Number of heavy atoms RDKit 35
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.16
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 19
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.24
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Silibinin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.3742
Silibinin
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -7.89
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 0.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No
Silibinin
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000221130GSR864
ENSP00000227507CCND1981
ENSP00000228872CDKN1B900
ENSP00000231449IL4800
ENSP00000241052CAT836
ENSP00000244741CDKN1A700
ENSP00000245206GOT2762
ENSP00000256442CCNB1900
ENSP00000257904CDK4900
ENSP00000260682CYP2C9742
ENSP00000263025MAPK3900
ENSP00000263817ABCB11723
ENSP00000265517MTTP800
ENSP00000265724ABCB1830
ENSP00000266970CDK2900
ENSP00000269305TP53727
ENSP00000278616ATM700
ENSP00000295453ALPPL2845
ENSP00000302111MGMT746
ENSP00000304845UGT1A1700
ENSP00000311032CASP3738
ENSP00000312664CASP2700
ENSP00000318822BID700
ENSP00000330237CASP9700
ENSP00000337459NOS1786
ENSP00000337915CYP3A4925
ENSP00000351273CASP8700
ENSP00000353483MAPK8725
ENSP00000355759PARP1700
ENSP00000356954CTGF815
ENSP00000359539GOT1763
ENSP00000361125VEGFA816
ENSP00000361405MMP9728
ENSP00000363512ALOX5900
ENSP00000363965ALPL844
ENSP00000364310H2AFX700
ENSP00000369927AKR1C3700
ENSP00000372023CHEK2700
ENSP00000375881ALPP843
ENSP00000389338MAPK9700
ENSP00000401303SHC1900
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.