(3R)-5-hydroxy-3-[(4-hydroxyphenyl)methyl]-6,7,8-trimethoxy-2,3-dihydrochromen-4-one

Details

• Internal ID: 55a1dbc5-e03a-4e7b-aac4-c5b56ab4cc67
• Taxonomy: Phenylpropanoids and polyketides > Homoisoflavonoids > Homoisoflavans > Homoisoflavanones
• IUPAC Name: (3R)-5-hydroxy-3-[(4-hydroxyphenyl)methyl]-6,7,8-trimethoxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): COC1=C(C(=C2C(=C1O)C(=O)C(CO2)CC3=CC=C(C=C3)O)OC)OC
• SMILES (Isomeric): COC1=C(C(=C2C(=C1O)C(=O)[C@@H](CO2)CC3=CC=C(C=C3)O)OC)OC
• InChI: InChI=1S/C19H20O7/c1-23-17-15(22)13-14(21)11(8-10-4-6-12(20)7-5-10)9-26-16(13)18(24-2)19(17)25-3/h4-7,11,20,22H,8-9H2,1-3H3/t11-/m1/s1
• InChI Key: SZCVKSHTEKEQNX-LLVKDONJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₀O₇
• Molecular Weight: 360.40 g/mol
• Exact Mass: 360.12090297 g/mol
• Topological Polar Surface Area (TPSA): 94.40 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.56
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9462	94.62%
Caco-2	+	0.7281	72.81%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7779	77.79%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8888	88.88%
OATP1B3 inhibitior	-	0.3316	33.16%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5524	55.24%
P-glycoprotein inhibitior	-	0.5511	55.11%
P-glycoprotein substrate	-	0.7209	72.09%
CYP3A4 substrate	+	0.5673	56.73%
CYP2C9 substrate	-	0.8046	80.46%
CYP2D6 substrate	-	0.7445	74.45%
CYP3A4 inhibition	-	0.7492	74.92%
CYP2C9 inhibition	-	0.5531	55.31%
CYP2C19 inhibition	+	0.6687	66.87%
CYP2D6 inhibition	-	0.7235	72.35%
CYP1A2 inhibition	+	0.8764	87.64%
CYP2C8 inhibition	+	0.6470	64.70%
CYP inhibitory promiscuity	+	0.6970	69.70%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7086	70.86%
Eye corrosion	-	0.9770	97.70%
Eye irritation	-	0.5271	52.71%
Skin irritation	-	0.8094	80.94%
Skin corrosion	-	0.9810	98.10%
Ames mutagenesis	+	0.5446	54.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.7283	72.83%
Micronuclear	+	0.6959	69.59%
Hepatotoxicity	+	0.5104	51.04%
skin sensitisation	-	0.9033	90.33%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.7820	78.20%
Acute Oral Toxicity (c)	III	0.6760	67.60%
Estrogen receptor binding	+	0.8873	88.73%
Androgen receptor binding	+	0.7229	72.29%
Thyroid receptor binding	+	0.6834	68.34%
Glucocorticoid receptor binding	+	0.7346	73.46%
Aromatase binding	-	0.6021	60.21%
PPAR gamma	+	0.7035	70.35%
Honey bee toxicity	-	0.8665	86.65%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.8451	84.51%

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	97.15%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.98%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.73%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.65%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.01%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.58%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.41%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.07%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.90%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.88%	86.33%
CHEMBL4040	P28482	MAP kinase ERK2	84.89%	83.82%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.12%	95.89%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	82.12%	93.10%

Plants that contains it

• Veltheimia bracteata

Cross-Links

• PubChem: 9998603
• LOTUS: LTS0229097
• wikiData: Q105263998