2-(2,5-Dihydroxy-4-methoxyphenyl)-5-hydroxy-6,7,8-trimethoxychromen-4-one

Details

• Internal ID: 543e1ab5-2199-4725-8629-118ad2de0016
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 8-O-methylated flavonoids
• IUPAC Name: 2-(2,5-dihydroxy-4-methoxyphenyl)-5-hydroxy-6,7,8-trimethoxychromen-4-one
• SMILES (Canonical): COC1=C(C=C(C(=C1)O)C2=CC(=O)C3=C(C(=C(C(=C3O2)OC)OC)OC)O)O
• SMILES (Isomeric): COC1=C(C=C(C(=C1)O)C2=CC(=O)C3=C(C(=C(C(=C3O2)OC)OC)OC)O)O
• InChI: InChI=1S/C19H18O9/c1-24-13-6-9(20)8(5-10(13)21)12-7-11(22)14-15(23)17(25-2)19(27-4)18(26-3)16(14)28-12/h5-7,20-21,23H,1-4H3
• InChI Key: WARHVXWFMMHDLD-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₈O₉
• Molecular Weight: 390.30 g/mol
• Exact Mass: 390.09508215 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.61
• H-Bond Acceptor: 9
• 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	+	0.9711	97.11%
Caco-2	+	0.7097	70.97%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7936	79.36%
OATP2B1 inhibitior	-	0.7062	70.62%
OATP1B1 inhibitior	+	0.8757	87.57%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.4831	48.31%
P-glycoprotein inhibitior	+	0.6655	66.55%
P-glycoprotein substrate	-	0.8040	80.40%
CYP3A4 substrate	+	0.5281	52.81%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	-	0.7237	72.37%
CYP2C9 inhibition	-	0.6863	68.63%
CYP2C19 inhibition	+	0.6566	65.66%
CYP2D6 inhibition	-	0.8329	83.29%
CYP1A2 inhibition	+	0.8642	86.42%
CYP2C8 inhibition	+	0.5375	53.75%
CYP inhibitory promiscuity	+	0.7231	72.31%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5851	58.51%
Eye corrosion	-	0.9825	98.25%
Eye irritation	-	0.6002	60.02%
Skin irritation	-	0.7275	72.75%
Skin corrosion	-	0.9759	97.59%
Ames mutagenesis	-	0.5564	55.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.6770	67.70%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.9511	95.11%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.7016	70.16%
Acute Oral Toxicity (c)	III	0.4741	47.41%
Estrogen receptor binding	+	0.8845	88.45%
Androgen receptor binding	+	0.6954	69.54%
Thyroid receptor binding	+	0.6874	68.74%
Glucocorticoid receptor binding	+	0.8078	80.78%
Aromatase binding	+	0.6648	66.48%
PPAR gamma	+	0.7143	71.43%
Honey bee toxicity	-	0.8621	86.21%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6649	66.49%
Fish aquatic toxicity	+	0.8969	89.69%

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	98.10%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.86%	94.00%
CHEMBL2581	P07339	Cathepsin D	93.14%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.74%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.18%	89.00%
CHEMBL3194	P02766	Transthyretin	92.10%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.95%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.09%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.05%	99.17%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	83.05%	98.11%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.85%	93.99%
CHEMBL2535	P11166	Glucose transporter	82.71%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	82.19%	94.73%

Plants that contains it

• Gutierrezia microcephala

Cross-Links

• PubChem: 162894567
• LOTUS: LTS0026162
• wikiData: Q105300424