Compound: silibinin
SMILES: O=C1c2c(O[C@@H]([C@H]1O)c3cc4O[C@H](c5cc(OC)c(O)cc5)[C@@H](CO)Oc4cc3)cc(O)cc2O
InChIKey: SEBFKMXJBCUCAI-HKTJVKLFSA-N
Synonyms: silibinin, Silymarin I, Flavobin, Silybine, Silibinine, Silliver, Silymarine I, Silibinina, Silibininum, Legalon, (2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one, CHEBI:9144, (2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-4H-chromen-4-one, Silibinin a-silibinin b mixt., (2R,3R)-3,5,7-trihydroxy-2-((2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl)-2,3-dihydro-4H-chromen-4-one, (2R,3R)-3,5,7-trihydroxy-2-((2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl)-2,3-dihydrochromen-4-one, RefChem:183059, 4RKY41TBTF, 245-302-5, (2R,3R)-3,5,7-trihydroxy-2-(3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl)-2,3-dihydrochromen-4-one, Silybin, 22888-70-6, Silybin A, Silibinin A, Silibinin [INN], (2R,3R)-3,5,7-trihydroxy-2-((2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)chroman-4-one, Silymarine, ( inverted exclamation markA)-SILYBIN, Flavobin Spofa, MFCD00872186, NSC-651520, (+/-)-SILYBIN, DTXSID8026018, 33X338MNE4, Silibinin (INN), NSC651520, 4H-1-Benzopyran-4-one,2-[(2R,3R)-2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)-, NCGC00091057-01, (2r,3r)-2-[(2r,3r)-2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5,7-trihydroxy-4h-1-benzopyran-4-one, (2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxy-phenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chroman-4-one, (2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one, 1265089-69-7, DTXCID106018, Silibinine [INN-French], Silibininum [INN-Latin], Silibinina [INN-Spanish], 7C3MT, rel-(2R,3R)-3,5,7-Trihydroxy-2-((2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)chroman-4-one, CAS-22888-70-6, EINECS 245-302-5, NSC 651520, Silybin;Silibinin A;Silymarin I, silybinin, UNII-33X338MNE4, CCRIS 9378, Silymarin A, 4H-1-Benzopyran-4-one, 2-((2R,3R)-2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl)-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)-, 4H-1-Benzopyran-4-one, 2-[(2R,3R)-2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)-, ()-Silybin, Legalon (TN), Silibinin (Silybin), Silybin A (Standard), Spectrum2_001694, Spectrum3_001132, Spectrum4_001978, Spectrum5_001893, SILYBIN A [MI], BSPBio_002623, KBioGR_002481, Milk thistle dry extract HRS, MLS001304057, SCHEMBL324884, SPECTRUM1505256, SPBio_001648, CHEMBL431701, MEGxp0_001301, orb1307850, orb2299464, orb3140637, SCHEMBL29392068, SCHEMBL29399173, GTPL12449, KBio3_002123, HMS1922P05, HMS2232P03, HMS6018N08, 2,3-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-6-(3,5,7-trihydroxy-4-oxobenzopyran-2-yl)benzodioxin, MSK40325, Tox21_111070, Tox21_200755, BDBM50084982, CCG-38779, EBC-17130, HY-13748R, MFCD03225424, s2357, ( inverted exclamation mark_)-Silybin, AKOS004119918, Tox21_111070_1, DB09298, DS-9661, SDCCGMLS-0066916.P001, SMP2_000323, NCGC00091057-02, NCGC00091057-03, NCGC00091057-05, NCGC00258309-01, Silybin A (constituent of milk thistle), 3,5,7-Trihydroxy-2-(3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxan-6-yl)-4-chromanone, 4H-1-Benzopyran-4-one, 2,3-dihydro-2-(2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl)-3,5,7-trihydroxy-, (2R-(2-alpha,3-beta,6(2R*,3R*)))-, 4H-1-Benzopyran-4-one, 2-(2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl)-2,3-dihydro-3,5,7-trihydroxy-, (2R-(2alpha,3beta,6(2R*,3R*)))-, BP-30210, DA-57872, HY-13748, SMR000718776, SY067261, SY103655, SBI-0207018.P001, HY-139637, CS-0226432, Silybin ASilibinin A; Silybin A; Silymarin I, D08515, E82516, AB00876265_06, F551327, F870214, Q425702, SR-01000799140, SR-01000799140-2, BRD-K80353138-001-02-2, BRD-K80353138-001-07-1, BRD-K80353138-001-12-1, BRD-K80353138-001-13-9, SILYBIN A (CONSTITUENT OF MILK THISTLE) [DSC], (2R,3R)-3,5,7-Trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxy-phenyl)-2-hydroxymethyl-2,3-dihydro-benzo[1,4]dioxin-6-yl]-chroman-4-one, (2R,3R)-3,5,7-Trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-4H-1-benzopyran-4-one, (2R,3R)-3,5,7-Trihydroxy-2-[3-(4-hydroxy-3-methoxy-phenyl)-2-hydroxymethyl-2,3-dihydro-benzo[1,4]dioxin-6-yl]-chroman-4-one, 3,5,7-Trihydroxy-2-(3-(4-hydroxy-3-methoxyphenyl)- 2-(hydroxymethyl)-1,4-benzodioxan-6-yl)-4-chromanone, 3,5,7-Trihydroxy-2-[3-(4-hydroxy-3-methoxy-phenyl)-2-hydroxymethyl-2,3-dihydro-benzo[1,4]dioxin-6-yl]-chroman-4-one, 3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-(2R,3R)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl]-(2R,3R)-3,4-dihydro-2H-4-chromenone
Theoretical properties:
molecular_formula: C25H22O10
molecular_weight: 482.4 g/mol
exact_mass: 482.12129689 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 5
hydrogen_bond_acceptor_count: 10
rotatable_bond_count: 4
heavy_atom_count: 35
topological_polar_surface_area: 155 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Silibinin is a flavonolignan isolated from milk thistle, Silybum marianum, that has been shown to exhibit antioxidant and antineoplastic activities. It has a role as an antioxidant, an antineoplastic agent, a hepatoprotective agent and a plant metabolite. It is a secondary alpha-hydroxy ketone, a polyphenol, an aromatic ether, a benzodioxine and a flavonolignan.
chebi: A flavonolignan isolated from milk thistle, <em>Silybum marianum</em>, that has been shown to exhibit antioxidant and antineoplastic activities.
chembl: SILYBIN A is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Silibinin (INN), also known as silybin (both from Silybum, the generic name of the plant from which it is extracted), is the major active constituent of silymarin, a standardized extract of the milk thistle, containing a mixture of flavonolignans consisting of silibinin, isosilibinin, silychristin, silidianin, and others.  Silibinin itself is a mixture of two diastereomers, silybin A and silybin B, in approximately equimolar ratio.  Silibinin is used in pure forms as a medication, and more frequently as an active ingredient in milk thistle–derived herbal supplements.