Silymarin

Details

• Internal ID: 9b37516c-ed16-4237-8506-910c550b06db
• Taxonomy: Lignans, neolignans and related compounds > Flavonolignans
• IUPAC Name: 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
• 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)C2C(OC3=C(O2)C=C(C=C3)C4C(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
• InChI Key: SEBFKMXJBCUCAI-UHFFFAOYSA-N
• Popularity: 2,717 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

• Silybin
• 65666-07-1
• Legalon
• Silimarin
• Flavobion
• Silibin
• (2R,3R)-3,5,7-trihydroxy-2-[(2R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
• 142796-20-1
• Legalon 70
• 802918-57-6
• 84604-20-6
• 3,5,7-trihydroxy-2-(3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)chroman-4-one
• 3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-4H-chromen-4-one
• 3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one
• 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-
• SMR000058272
• UNII-4RKY41TBTF
• UNII-822I9LEJ7S
• SR-01000000093
• 36804-17-8
• CCRIS 7096
• Silybin;Silibinin A;Silymarin I
• Apihepar
• Laragon
• Silmyarin
• MFCD00872186
• Silibinin, INN
• Silymarin,(S)
• Silybin (7CI)
• Silybum substance E6
• MLS000028529
• MLS006011786
• SCHEMBL678427
• DTXSID00860287
• CHEBI:125451
• SEBFKMXJBCUCAI-UHFFFAOYSA-N
• HMS1608M08
• HMS2232P05
• HMS3372B20
• HMS3373N17
• HMS3656K09
• (2S)-3,5,7-trihydroxy-2-[(2S,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
• 4-Chromanone, 3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxan-6-yl]-
• 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-
• 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-
• 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-[2.alpha.,3.beta.,6(2R*,3R*)]]-
• BCP30337
• Silymarin group, mixture of isomers
• BBL027841
• BDBM50218276
• STK396325
• AKOS000546856
• CS-O-02368
• NCGC00018179-02
• NCGC00018179-03
• NCGC00018179-04
• NCGC00089738-02
• NCGC00089738-03
• 3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxy-phenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chroman-4-one
• 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
• SY067261
• VS-08600
• FT-0656490
• FT-0674587
• FT-0775414
• C07610
• Silybin; Silibinin A; Silymarin I; Silymarine I
• SR-01000000093-5
• SR-01000000093-6
• SR-01000000093-7
• SR-01000000093-8
• SR-01000000093-9
• Q27216069
• B0005-464964
• 2-[2,3-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-3,5,7-trihydroxy-2,3-dihydro-4H-1-benzopyran-4-one
• 3,5,7-Trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-4H-1-benzopyran-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
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	15848.9 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	14125.4 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	25118.9 nM; 39810.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL261	P00915	Carbonic anhydrase I	1490 nM	Ki	PMID: 20674354
CHEMBL205	P00918	Carbonic anhydrase II	2510 nM	Ki	PMID: 20674354
CHEMBL2885	P07451	Carbonic anhydrase III	6430 nM	Ki	PMID: 20674354
CHEMBL3729	P22748	Carbonic anhydrase IV	8960 nM	Ki	PMID: 20674354
CHEMBL3594	Q16790	Carbonic anhydrase IX	10150 nM	Ki	PMID: 20674354
CHEMBL4789	P35218	Carbonic anhydrase VA	4080 nM	Ki	PMID: 20674354
CHEMBL3969	Q9Y2D0	Carbonic anhydrase VB	4560 nM	Ki	PMID: 20674354
CHEMBL3025	P23280	Carbonic anhydrase VI	9700 nM	Ki	PMID: 20674354
CHEMBL2326	P43166	Carbonic anhydrase VII	4710 nM	Ki	PMID: 20674354
CHEMBL3242	O43570	Carbonic anhydrase XII	9050 nM	Ki	PMID: 20674354
CHEMBL3912	Q8N1Q1	Carbonic anhydrase XIII	4820 nM	Ki	PMID: 20674354
CHEMBL3510	Q9ULX7	Carbonic anhydrase XIV	11640 nM	Ki	PMID: 20674354
CHEMBL4096	P04637	Cellular tumor antigen p53	15848.9 nM	Potency	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	5000 nM	Ki	PMID: 16248836
CHEMBL340	P08684	Cytochrome P450 3A4	12589.3 nM; 10000 nM; 10000 nM; 12589.3 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2608	P10253	Lysosomal alpha-glucosidase	35481.3 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	22387.2 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	17.8 nM; 17.8 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL1697668	Q9Y6L6	Solute carrier organic anion transporter family member 1B1	9700 nM; 6165.95 nM	IC50; IC50	PMID: 23401473; PMID: 23571415
CHEMBL1743121	Q9NPD5	Solute carrier organic anion transporter family member 1B3	2700 nM; 4265.8 nM	IC50; IC50	PMID: 23401473; PMID: 23571415
CHEMBL1743124	O94956	Solute carrier organic anion transporter family member 2B1	4500 nM	IC50	PMID: 23401473
CHEMBL204	P00734	Thrombin	25000 nM; 20900 nM	IC50; IC50	PMID: 24610996; PMID: 24610996
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	2511.9 nM; 2511.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	1995.3 nM	Potency	via CMAUP

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
• Lycium chinense
• Silybum marianum

Cross-Links

• PubChem: 5213
• NPASS: NPC125039
• ChEMBL: CHEMBL1401508
• LOTUS: LTS0228416
• wikiData: Q27216069