Flavobion

Details

• Internal ID: 34440721-63f1-4e2a-9f66-77921fe98508
• Taxonomy: Lignans, neolignans and related compounds > Flavonolignans
• IUPAC Name: (3R)-3,5,7-trihydroxy-2-[(3R)-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]2C(OC3=C(O2)C=C(C=C3)C4[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-HHXGKTILSA-N
• Popularity: 1,135 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
• Atomic LogP (AlogP): 2.36
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• Legalon
• Silybin
• Legalon 70
• SILYMARIN
• CCRIS 7096
• PREVENTION 2 (SILYMARIN)
• SEBFKMXJBCUCAI-HHXGKTILSA-N
• LS-283
• 2-[2R,3R-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2R,3R-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9045	90.45%
Caco-2	-	0.8574	85.74%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6746	67.46%
OATP2B1 inhibitior	-	0.5684	56.84%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.8605	86.05%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9071	90.71%
P-glycoprotein inhibitior	+	0.9511	95.11%
P-glycoprotein substrate	-	0.8633	86.33%
CYP3A4 substrate	+	0.6009	60.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8031	80.31%
CYP3A4 inhibition	+	0.5057	50.57%
CYP2C9 inhibition	+	0.6354	63.54%
CYP2C19 inhibition	-	0.5992	59.92%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.7709	77.09%
CYP2C8 inhibition	+	0.5460	54.60%
CYP inhibitory promiscuity	+	0.7391	73.91%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7023	70.23%
Eye corrosion	-	0.9843	98.43%
Eye irritation	-	0.8041	80.41%
Skin irritation	-	0.7892	78.92%
Skin corrosion	-	0.9591	95.91%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5435	54.35%
Micronuclear	+	0.6759	67.59%
Hepatotoxicity	+	0.9875	98.75%
skin sensitisation	-	0.8875	88.75%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	+	0.7345	73.45%
Acute Oral Toxicity (c)	III	0.7236	72.36%
Estrogen receptor binding	+	0.8483	84.83%
Androgen receptor binding	+	0.7342	73.42%
Thyroid receptor binding	+	0.6674	66.74%
Glucocorticoid receptor binding	+	0.7895	78.95%
Aromatase binding	-	0.6019	60.19%
PPAR gamma	+	0.6508	65.08%
Honey bee toxicity	-	0.8065	80.65%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	-	0.5170	51.70%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	17.8 nM	Potency	via Super-PRED

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

• Silybum marianum

Cross-Links

• PubChem: 24832061
• NPASS: NPC247525
• LOTUS: LTS0246473
• wikiData: Q104251434