2-(3,4-Dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-6,8-dimethyl-4H-1-benzopyran-4-one

Details

• Internal ID: c2bbfa4f-af06-4221-8995-db5a4861ea7e
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 7-O-methylated flavonoids
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-6,8-dimethylchromen-4-one
• SMILES (Canonical): CC1=C(C2=C(C(=C1OC)C)OC(=C(C2=O)OC)C3=CC(=C(C=C3)O)O)O
• SMILES (Isomeric): CC1=C(C2=C(C(=C1OC)C)OC(=C(C2=O)OC)C3=CC(=C(C=C3)O)O)O
• InChI: InChI=1S/C19H18O7/c1-8-14(22)13-15(23)19(25-4)18(10-5-6-11(20)12(21)7-10)26-17(13)9(2)16(8)24-3/h5-7,20-22H,1-4H3
• InChI Key: XICKQNFAJAXFNI-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₈O₇
• Molecular Weight: 358.30 g/mol
• Exact Mass: 358.10525291 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.21
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• LMPK12112726

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9464	94.64%
Caco-2	+	0.6209	62.09%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7784	77.84%
OATP2B1 inhibitior	-	0.5642	56.42%
OATP1B1 inhibitior	+	0.9390	93.90%
OATP1B3 inhibitior	+	0.9791	97.91%
MATE1 inhibitior	-	0.6000	60.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6123	61.23%
P-glycoprotein inhibitior	-	0.5343	53.43%
P-glycoprotein substrate	-	0.8990	89.90%
CYP3A4 substrate	+	0.5213	52.13%
CYP2C9 substrate	-	0.6600	66.00%
CYP2D6 substrate	-	0.8464	84.64%
CYP3A4 inhibition	-	0.7900	79.00%
CYP2C9 inhibition	-	0.8973	89.73%
CYP2C19 inhibition	-	0.7079	70.79%
CYP2D6 inhibition	-	0.9069	90.69%
CYP1A2 inhibition	+	0.8325	83.25%
CYP2C8 inhibition	+	0.7596	75.96%
CYP inhibitory promiscuity	+	0.5295	52.95%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6022	60.22%
Eye corrosion	-	0.9832	98.32%
Eye irritation	+	0.5238	52.38%
Skin irritation	-	0.7279	72.79%
Skin corrosion	-	0.9633	96.33%
Ames mutagenesis	+	0.6763	67.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.6434	64.34%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	-	0.9405	94.05%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.7883	78.83%
Acute Oral Toxicity (c)	II	0.4732	47.32%
Estrogen receptor binding	+	0.8335	83.35%
Androgen receptor binding	+	0.8037	80.37%
Thyroid receptor binding	+	0.5676	56.76%
Glucocorticoid receptor binding	+	0.8080	80.80%
Aromatase binding	+	0.6338	63.38%
PPAR gamma	+	0.7959	79.59%
Honey bee toxicity	-	0.8788	87.88%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9122	91.22%

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	99.34%	91.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.16%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.77%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.47%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.40%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.20%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.49%	86.33%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	88.40%	98.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.44%	94.45%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	85.53%	93.65%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.27%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	82.62%	94.73%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	81.80%	94.42%

Plants that contains it

• Piliostigma thonningii

Cross-Links

• PubChem: 10642123
• LOTUS: LTS0041004
• wikiData: Q105328413