4-[(2S,3S)-3-(3,5-dihydroxyphenyl)-4-hydroxy-6-[2-(4-hydroxyphenyl)ethyl]-2,3-dihydro-1-benzofuran-2-yl]benzene-1,3-diol

Details

• Internal ID: 4c39f00d-0437-4f5c-968c-cf2047dce285
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 4-[(2S,3S)-3-(3,5-dihydroxyphenyl)-4-hydroxy-6-[2-(4-hydroxyphenyl)ethyl]-2,3-dihydro-1-benzofuran-2-yl]benzene-1,3-diol
• SMILES (Canonical): C1=CC(=CC=C1CCC2=CC(=C3C(C(OC3=C2)C4=C(C=C(C=C4)O)O)C5=CC(=CC(=C5)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1CCC2=CC(=C3[C@@H]([C@H](OC3=C2)C4=C(C=C(C=C4)O)O)C5=CC(=CC(=C5)O)O)O)O
• InChI: InChI=1S/C28H24O7/c29-18-5-3-15(4-6-18)1-2-16-9-24(34)27-25(10-16)35-28(22-8-7-19(30)14-23(22)33)26(27)17-11-20(31)13-21(32)12-17/h3-14,26,28-34H,1-2H2/t26-,28+/m0/s1
• InChI Key: ILEDQUFAIVUAIX-XTEPFMGCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₄O₇
• Molecular Weight: 472.50 g/mol
• Exact Mass: 472.15220310 g/mol
• Topological Polar Surface Area (TPSA): 131.00 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 4.97
• H-Bond Acceptor: 7
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9404	94.04%
Caco-2	-	0.8674	86.74%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7206	72.06%
OATP2B1 inhibitior	+	0.5709	57.09%
OATP1B1 inhibitior	+	0.8306	83.06%
OATP1B3 inhibitior	+	0.8406	84.06%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7476	74.76%
P-glycoprotein inhibitior	+	0.7331	73.31%
P-glycoprotein substrate	-	0.5721	57.21%
CYP3A4 substrate	+	0.5886	58.86%
CYP2C9 substrate	-	0.6025	60.25%
CYP2D6 substrate	+	0.5974	59.74%
CYP3A4 inhibition	+	0.6427	64.27%
CYP2C9 inhibition	+	0.9048	90.48%
CYP2C19 inhibition	+	0.8200	82.00%
CYP2D6 inhibition	-	0.7755	77.55%
CYP1A2 inhibition	+	0.8870	88.70%
CYP2C8 inhibition	+	0.8294	82.94%
CYP inhibitory promiscuity	+	0.9476	94.76%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.4544	45.44%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.6723	67.23%
Skin irritation	-	0.5969	59.69%
Skin corrosion	-	0.9129	91.29%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7667	76.67%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8016	80.16%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.7784	77.84%
Acute Oral Toxicity (c)	III	0.3264	32.64%
Estrogen receptor binding	+	0.7960	79.60%
Androgen receptor binding	+	0.7936	79.36%
Thyroid receptor binding	+	0.7182	71.82%
Glucocorticoid receptor binding	+	0.7433	74.33%
Aromatase binding	+	0.5523	55.23%
PPAR gamma	+	0.8255	82.55%
Honey bee toxicity	-	0.7891	78.91%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9333	93.33%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL233	P35372	Mu opioid receptor	96.37%	97.93%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.18%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.95%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.68%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	92.64%	93.99%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	91.88%	95.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.84%	99.17%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	86.55%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	85.45%	94.73%
CHEMBL236	P41143	Delta opioid receptor	84.53%	99.35%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	83.47%	96.37%
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	83.40%	96.42%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.39%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.96%	86.33%
CHEMBL4040	P28482	MAP kinase ERK2	82.35%	83.82%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	82.30%	93.40%
CHEMBL5939	Q9NZ08	Endoplasmic reticulum aminopeptidase 1	82.08%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.99%	97.09%
CHEMBL2535	P11166	Glucose transporter	81.53%	98.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.44%	99.15%
CHEMBL3891	P07384	Calpain 1	81.30%	93.04%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.76%	91.71%
CHEMBL3194	P02766	Transthyretin	80.73%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.31%	89.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.01%	95.89%

Plants that contains it

• Gnetum africanum

Cross-Links

• PubChem: 11113470
• LOTUS: LTS0003553
• wikiData: Q105115130