3-[3,4-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-3,4-dihydro-2H-chromen-6-yl]prop-2-enal

Details

• Internal ID: 8bd4eca2-a26e-4a13-a0f9-a3d74fb4bffc
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Leucoanthocyanidins
• IUPAC Name: 3-[3,4-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-3,4-dihydro-2H-chromen-6-yl]prop-2-enal
• SMILES (Canonical): COC1=CC(=CC2=C1OC(C(C2O)O)C3=CC(=C(C=C3)O)OC)C=CC=O
• SMILES (Isomeric): COC1=CC(=CC2=C1OC(C(C2O)O)C3=CC(=C(C=C3)O)OC)C=CC=O
• InChI: InChI=1S/C20H20O7/c1-25-15-10-12(5-6-14(15)22)19-18(24)17(23)13-8-11(4-3-7-21)9-16(26-2)20(13)27-19/h3-10,17-19,22-24H,1-2H3
• InChI Key: MYZLDNDAKRMNRG-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₇
• Molecular Weight: 372.40 g/mol
• Exact Mass: 372.12090297 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 2.15
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9673	96.73%
Caco-2	-	0.6556	65.56%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7222	72.22%
OATP2B1 inhibitior	-	0.8575	85.75%
OATP1B1 inhibitior	+	0.8894	88.94%
OATP1B3 inhibitior	+	0.9924	99.24%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.6825	68.25%
P-glycoprotein inhibitior	-	0.5452	54.52%
P-glycoprotein substrate	-	0.8539	85.39%
CYP3A4 substrate	+	0.5782	57.82%
CYP2C9 substrate	-	0.5892	58.92%
CYP2D6 substrate	-	0.7726	77.26%
CYP3A4 inhibition	+	0.5463	54.63%
CYP2C9 inhibition	+	0.5529	55.29%
CYP2C19 inhibition	+	0.7551	75.51%
CYP2D6 inhibition	-	0.8336	83.36%
CYP1A2 inhibition	+	0.7952	79.52%
CYP2C8 inhibition	+	0.6566	65.66%
CYP inhibitory promiscuity	+	0.7713	77.13%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5591	55.91%
Eye corrosion	-	0.9825	98.25%
Eye irritation	-	0.8158	81.58%
Skin irritation	-	0.6673	66.73%
Skin corrosion	-	0.9463	94.63%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6514	65.14%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8791	87.91%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.6487	64.87%
Acute Oral Toxicity (c)	II	0.5094	50.94%
Estrogen receptor binding	+	0.6851	68.51%
Androgen receptor binding	+	0.5730	57.30%
Thyroid receptor binding	+	0.6055	60.55%
Glucocorticoid receptor binding	+	0.5922	59.22%
Aromatase binding	-	0.5508	55.08%
PPAR gamma	-	0.5203	52.03%
Honey bee toxicity	-	0.8057	80.57%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9612	96.12%

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	98.15%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.50%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.58%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.87%	96.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.48%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.66%	89.00%
CHEMBL3194	P02766	Transthyretin	91.28%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	91.13%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.38%	86.33%
CHEMBL2535	P11166	Glucose transporter	84.12%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.33%	99.17%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.31%	97.14%

Plants that contains it

• Premna fulva

Cross-Links

• PubChem: 162953462
• LOTUS: LTS0034643
• wikiData: Q105175311