Silibinin B

Details

• Internal ID: 6e46b932-8a94-4d02-adf0-f6c4fa529a77
• Taxonomy: Lignans, neolignans and related compounds > Flavonolignans
• IUPAC Name: (2R,3R)-3,5,7-trihydroxy-2-[(2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)[C@H]2[C@@H](OC3=C(O2)C=C(C=C3)[C@@H]4[C@H](C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)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+/m0/s1
• InChI Key: SEBFKMXJBCUCAI-WAABAYLZSA-N
• Popularity: 1,144 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₂O₁₀
• Molecular Weight: 482.40 g/mol
• Exact Mass: 482.12129689 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: 2.40

Synonyms

• 142797-34-0
• Silibinin B
• (2R,3R)-3,5,7-trihydroxy-2-[(2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
• 853OHH1429
• DTXSID30858697
• (2R,3R)-3,5,7-trihydroxy-2-((2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl)-2,3-dihydrochromen-4-one
• RefChem:49959
• DTXCID703580
• SILYBIN (A and B)(P)
• (2R,3R)-3,5,7-trihydroxy-2-((2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)chroman-4-one
• Flavobion
• (2R,3R)-3,5,7-trihydroxy-2-[(2S,3S)-3-(4-hydroxy-3-methoxy-phenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chroman-4-one
• 308831-37-0
• rel-(2R,3R)-3,5,7-Trihydroxy-2-((2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)chroman-4-one
• Legalon 70
• CCRIS 7096
• Silymarin B
• UNII-853OHH1429
• Silybin A and B
• 4H-1-BENZOPYRAN-4-ONE, 2-((2S,3S)-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-[(2S,3S)-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-[(2S,3S)-2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)-; 1,4-Benzodioxin, 4H-1-benzopyran-4-one deriv.; (2R,3R)-2-[(2S,3S)-2,3-Dihydro-3-(4-hydroxy-3-metho
• Milk thistle [NF]
• Silymarin + Melatonin
• Silybin B (Standard)
• SILYBIN B [MI]
• UNII-U946SH95EE
• SCHEMBL751461
• Silybin B, analytical standard
• CHEMBL592675
• orb1684217
• U946SH95EE
• SCHEMBL29356290
• SCHEMBL29716717
• HY-N7046R
• CHEBI:207762
• GLXC-22706
• HY-N7046
• BDBM50088491
• AKOS015912848
• (2r,3r)-2-[(2s,3s)-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
• FS139048
• FS180849
• MS-28965
• CS-0101839
• Q27269584
• SILYBIN B (CONSTITUENT OF MILK THISTLE) [DSC]
• (2R,3R)-3,5,7-trihydroxy-2-[(2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-4H-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3397	P11712	Cytochrome P450 2C9	8200 nM	IC50	PMID: 23260576
CHEMBL1293235	P02545	Prelamin-A/C	17.8 nM	Potency	via Super-PRED
CHEMBL1697668	Q9Y6L6	Solute carrier organic anion transporter family member 1B1	8500 nM	IC50	PMID: 23401473
CHEMBL1743121	Q9NPD5	Solute carrier organic anion transporter family member 1B3	5000 nM	IC50	PMID: 23401473
CHEMBL1743124	O94956	Solute carrier organic anion transporter family member 2B1	800 nM	IC50	PMID: 23401473

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.12%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.60%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.51%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.44%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.41%	89.00%
CHEMBL2581	P07339	Cathepsin D	91.40%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.21%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.78%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.75%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.09%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.72%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.76%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.59%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.70%	99.23%
CHEMBL3194	P02766	Transthyretin	83.19%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	83.15%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.48%	92.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.82%	97.14%

Plants that contains it

• Anastatica hierochuntica
• Silybum marianum

Cross-Links

• PubChem: 1548994
• NPASS: NPC7688
• ChEMBL: CHEMBL592675
• LOTUS: LTS0068471
• wikiData: Q27269584