(3R)-9-[(2S)-5,7-dihydroxy-4-oxo-2,3-dihydrochromen-2-yl]-3-hydroxy-10-(4-hydroxy-3-methoxyphenyl)-4-oxatricyclo[4.3.1.03,7]dec-8-en-2-one

Details

• Internal ID: 4d8d61dc-50bc-4dfb-88f3-e6dba6784328
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Cyclohexylphenols
• IUPAC Name: (3R)-9-[(2S)-5,7-dihydroxy-4-oxo-2,3-dihydrochromen-2-yl]-3-hydroxy-10-(4-hydroxy-3-methoxyphenyl)-4-oxatricyclo[4.3.1.03,7]dec-8-en-2-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C2C3COC4(C3C=C(C2C4=O)C5CC(=O)C6=C(C=C(C=C6O5)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2C3CO[C@@]4(C3C=C(C2C4=O)[C@@H]5CC(=O)C6=C(C=C(C=C6O5)O)O)O)O
• InChI: InChI=1S/C25H22O9/c1-32-19-4-10(2-3-15(19)27)21-13-9-33-25(31)14(13)7-12(22(21)24(25)30)18-8-17(29)23-16(28)5-11(26)6-20(23)34-18/h2-7,13-14,18,21-22,26-28,31H,8-9H2,1H3/t13?,14?,18-,21?,22?,25+/m0/s1
• InChI Key: LNLXUVRWFZAUFM-KNQGUNCGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₂O₉
• Molecular Weight: 466.40 g/mol
• Exact Mass: 466.12638228 g/mol
• Topological Polar Surface Area (TPSA): 143.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 2.02
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9040	90.40%
Caco-2	-	0.8423	84.23%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6934	69.34%
OATP2B1 inhibitior	-	0.8561	85.61%
OATP1B1 inhibitior	+	0.9060	90.60%
OATP1B3 inhibitior	+	0.9548	95.48%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8774	87.74%
P-glycoprotein inhibitior	+	0.6461	64.61%
P-glycoprotein substrate	-	0.5397	53.97%
CYP3A4 substrate	+	0.6765	67.65%
CYP2C9 substrate	-	0.8034	80.34%
CYP2D6 substrate	-	0.8191	81.91%
CYP3A4 inhibition	-	0.6472	64.72%
CYP2C9 inhibition	+	0.6277	62.77%
CYP2C19 inhibition	+	0.5777	57.77%
CYP2D6 inhibition	-	0.8569	85.69%
CYP1A2 inhibition	-	0.7914	79.14%
CYP2C8 inhibition	+	0.6716	67.16%
CYP inhibitory promiscuity	+	0.5638	56.38%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5032	50.32%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.8809	88.09%
Skin irritation	-	0.7833	78.33%
Skin corrosion	-	0.9338	93.38%
Ames mutagenesis	-	0.5337	53.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4676	46.76%
Micronuclear	+	0.8033	80.33%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.8257	82.57%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.7268	72.68%
Acute Oral Toxicity (c)	I	0.4398	43.98%
Estrogen receptor binding	+	0.8909	89.09%
Androgen receptor binding	+	0.7226	72.26%
Thyroid receptor binding	+	0.5903	59.03%
Glucocorticoid receptor binding	+	0.8922	89.22%
Aromatase binding	+	0.5376	53.76%
PPAR gamma	+	0.6819	68.19%
Honey bee toxicity	-	0.6980	69.80%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9689	96.89%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.50%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.01%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.76%	94.45%
CHEMBL4208	P20618	Proteasome component C5	94.20%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.24%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.20%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.60%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.96%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.20%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.25%	86.33%
CHEMBL2581	P07339	Cathepsin D	88.56%	98.95%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	87.47%	93.40%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.09%	85.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.91%	92.94%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.46%	97.14%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	85.69%	92.68%
CHEMBL2535	P11166	Glucose transporter	85.41%	98.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.83%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.38%	97.09%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	83.69%	85.11%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.30%	92.62%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.77%	100.00%

Plants that contains it

• Silybum marianum

Cross-Links

• PubChem: 42608131
• NPASS: NPC279311