5,7,4'-Trihydroxy-6,2',3'-trimethoxy-flavone

Details

• Internal ID: 32cc3550-bcd5-4e33-af28-afc6c150ff1d
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 6-O-methylated flavonoids
• IUPAC Name: 5,7-dihydroxy-2-(4-hydroxy-2,3-dimethoxyphenyl)-6-methoxychromen-4-one
• SMILES (Canonical): COC1=C(C=CC(=C1OC)O)C2=CC(=O)C3=C(O2)C=C(C(=C3O)OC)O
• SMILES (Isomeric): COC1=C(C=CC(=C1OC)O)C2=CC(=O)C3=C(O2)C=C(C(=C3O)OC)O
• InChI: InChI=1S/C18H16O8/c1-23-16-8(4-5-9(19)18(16)25-3)12-6-10(20)14-13(26-12)7-11(21)17(24-2)15(14)22/h4-7,19,21-22H,1-3H3
• InChI Key: LGIAXRTUXPHMDS-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₆O₈
• Molecular Weight: 360.30 g/mol
• Exact Mass: 360.08451746 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.60
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9417	94.17%
Caco-2	+	0.7450	74.50%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6343	63.43%
OATP2B1 inhibitior	-	0.7006	70.06%
OATP1B1 inhibitior	+	0.9002	90.02%
OATP1B3 inhibitior	+	0.8767	87.67%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7464	74.64%
P-glycoprotein inhibitior	-	0.4892	48.92%
P-glycoprotein substrate	-	0.7946	79.46%
CYP3A4 substrate	+	0.5298	52.98%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	+	0.6154	61.54%
CYP2C9 inhibition	-	0.7484	74.84%
CYP2C19 inhibition	+	0.5640	56.40%
CYP2D6 inhibition	-	0.7310	73.10%
CYP1A2 inhibition	+	0.8610	86.10%
CYP2C8 inhibition	-	0.5741	57.41%
CYP inhibitory promiscuity	+	0.8068	80.68%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6142	61.42%
Eye corrosion	-	0.9818	98.18%
Eye irritation	+	0.6289	62.89%
Skin irritation	-	0.7187	71.87%
Skin corrosion	-	0.9573	95.73%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7469	74.69%
Micronuclear	+	0.8700	87.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.9352	93.52%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7871	78.71%
Acute Oral Toxicity (c)	III	0.5210	52.10%
Estrogen receptor binding	+	0.9229	92.29%
Androgen receptor binding	+	0.7667	76.67%
Thyroid receptor binding	+	0.6737	67.37%
Glucocorticoid receptor binding	+	0.8782	87.82%
Aromatase binding	+	0.7060	70.60%
PPAR gamma	+	0.7830	78.30%
Honey bee toxicity	-	0.8679	86.79%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8724	87.24%

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	99.42%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.05%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.49%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	92.32%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.08%	99.15%
CHEMBL3194	P02766	Transthyretin	91.63%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.11%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.06%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.33%	86.33%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.42%	80.78%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.66%	90.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.25%	85.14%
CHEMBL4208	P20618	Proteasome component C5	80.83%	90.00%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.45%	94.42%

Plants that contains it

• Mentha longifolia

Cross-Links

• PubChem: 91584129
• LOTUS: LTS0003377
• wikiData: Q105151364