(2S)-5,7-dihydroxy-2-[(2R,3R)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-4-yl]-2,3-dihydrochromen-4-one

Details

• Internal ID: 8c49c62d-3b87-4a72-9c0f-e28490aabbf9
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (2S)-5,7-dihydroxy-2-[(2R,3R)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-4-yl]-2,3-dihydrochromen-4-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C2C(C3=C(C=CC(=C3O2)O)C4CC(=O)C5=C(C=C(C=C5O4)O)O)CO)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)[C@H]2[C@H](C3=C(C=CC(=C3O2)O)[C@@H]4CC(=O)C5=C(C=C(C=C5O4)O)O)CO)O
• InChI: InChI=1S/C25H22O9/c1-32-20-6-11(2-4-15(20)28)24-14(10-26)22-13(3-5-16(29)25(22)34-24)19-9-18(31)23-17(30)7-12(27)8-21(23)33-19/h2-8,14,19,24,26-30H,9-10H2,1H3/t14-,19-,24-/m0/s1
• InChI Key: ODFCTVKAFKIYJI-ULNAFTNLSA-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): 146.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 3.43
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8749	87.49%
Caco-2	-	0.7881	78.81%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7522	75.22%
OATP2B1 inhibitior	-	0.5728	57.28%
OATP1B1 inhibitior	+	0.8953	89.53%
OATP1B3 inhibitior	+	0.9465	94.65%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8503	85.03%
P-glycoprotein inhibitior	+	0.8155	81.55%
P-glycoprotein substrate	-	0.6035	60.35%
CYP3A4 substrate	+	0.6476	64.76%
CYP2C9 substrate	-	0.8032	80.32%
CYP2D6 substrate	-	0.7695	76.95%
CYP3A4 inhibition	+	0.6040	60.40%
CYP2C9 inhibition	+	0.7577	75.77%
CYP2C19 inhibition	+	0.5637	56.37%
CYP2D6 inhibition	-	0.7949	79.49%
CYP1A2 inhibition	-	0.7182	71.82%
CYP2C8 inhibition	+	0.7444	74.44%
CYP inhibitory promiscuity	+	0.8664	86.64%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5558	55.58%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.8243	82.43%
Skin irritation	-	0.7995	79.95%
Skin corrosion	-	0.9528	95.28%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7401	74.01%
Micronuclear	+	0.6859	68.59%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.8701	87.01%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.5143	51.43%
Acute Oral Toxicity (c)	III	0.6879	68.79%
Estrogen receptor binding	+	0.8345	83.45%
Androgen receptor binding	+	0.7867	78.67%
Thyroid receptor binding	-	0.5198	51.98%
Glucocorticoid receptor binding	+	0.7638	76.38%
Aromatase binding	-	0.5706	57.06%
PPAR gamma	+	0.6132	61.32%
Honey bee toxicity	-	0.7891	78.91%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	-	0.4090	40.90%

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	98.91%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.29%	95.56%
CHEMBL2581	P07339	Cathepsin D	95.12%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.35%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.23%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.75%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.57%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.53%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.20%	95.89%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.13%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.36%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.01%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.01%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.17%	92.62%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.85%	86.92%
CHEMBL2535	P11166	Glucose transporter	84.12%	98.75%
CHEMBL4040	P28482	MAP kinase ERK2	84.05%	83.82%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.01%	96.21%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	81.54%	94.03%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.64%	97.14%
CHEMBL4208	P20618	Proteasome component C5	80.05%	90.00%

Plants that contains it

• Silybum marianum

Cross-Links

• PubChem: 162997693
• LOTUS: LTS0012111
• wikiData: Q104982850