3-[2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-8-yl]prop-2-enoic acid

Details

• Internal ID: 581a9a5f-7f08-4e3b-bdfd-368f30ec8baa
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones
• IUPAC Name: 3-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-8-yl]prop-2-enoic acid
• SMILES (Canonical): C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C(=C3O2)C=CC(=O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C(=C3O2)C=CC(=O)O)O)O)O)O
• InChI: InChI=1S/C18H12O8/c19-10-3-1-8(5-12(10)21)15-7-14(23)17-13(22)6-11(20)9(18(17)26-15)2-4-16(24)25/h1-7,19-22H,(H,24,25)
• InChI Key: DBBLAWYMYVZKML-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₂O₈
• Molecular Weight: 356.30 g/mol
• Exact Mass: 356.05321734 g/mol
• Topological Polar Surface Area (TPSA): 145.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.38
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8499	84.99%
Caco-2	-	0.6609	66.09%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5178	51.78%
OATP2B1 inhibitior	+	0.5904	59.04%
OATP1B1 inhibitior	+	0.9323	93.23%
OATP1B3 inhibitior	+	0.9669	96.69%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7449	74.49%
P-glycoprotein inhibitior	-	0.8912	89.12%
P-glycoprotein substrate	-	0.8668	86.68%
CYP3A4 substrate	-	0.5092	50.92%
CYP2C9 substrate	-	0.7974	79.74%
CYP2D6 substrate	-	0.8882	88.82%
CYP3A4 inhibition	-	0.6128	61.28%
CYP2C9 inhibition	+	0.5273	52.73%
CYP2C19 inhibition	-	0.8692	86.92%
CYP2D6 inhibition	-	0.9653	96.53%
CYP1A2 inhibition	-	0.8394	83.94%
CYP2C8 inhibition	+	0.6873	68.73%
CYP inhibitory promiscuity	-	0.7259	72.59%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6477	64.77%
Eye corrosion	-	0.9929	99.29%
Eye irritation	+	0.8858	88.58%
Skin irritation	+	0.4908	49.08%
Skin corrosion	-	0.9324	93.24%
Ames mutagenesis	-	0.5964	59.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.7588	75.88%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.7665	76.65%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.7783	77.83%
Acute Oral Toxicity (c)	II	0.6531	65.31%
Estrogen receptor binding	+	0.8554	85.54%
Androgen receptor binding	+	0.9407	94.07%
Thyroid receptor binding	-	0.5524	55.24%
Glucocorticoid receptor binding	+	0.8942	89.42%
Aromatase binding	+	0.7079	70.79%
PPAR gamma	+	0.8707	87.07%
Honey bee toxicity	-	0.8069	80.69%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9853	98.53%

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	98.40%	91.11%
CHEMBL3194	P02766	Transthyretin	94.45%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.36%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.49%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.97%	99.15%
CHEMBL1951	P21397	Monoamine oxidase A	89.07%	91.49%
CHEMBL2581	P07339	Cathepsin D	88.86%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.79%	86.33%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	87.52%	91.71%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	85.06%	89.23%
CHEMBL308	P06493	Cyclin-dependent kinase 1	84.54%	91.73%
CHEMBL3401	O75469	Pregnane X receptor	82.91%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.04%	94.45%

Plants that contains it

• Turnera diffusa

Cross-Links

• PubChem: 162864368
• LOTUS: LTS0104346
• wikiData: Q104974218