Sexangularetin

Details

• Internal ID: 35cbb8fb-2f42-4d0c-95de-e7e039c06846
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > Flavonols
• IUPAC Name: 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-8-methoxychromen-4-one
• SMILES (Canonical): COC1=C(C=C(C2=C1OC(=C(C2=O)O)C3=CC=C(C=C3)O)O)O
• SMILES (Isomeric): COC1=C(C=C(C2=C1OC(=C(C2=O)O)C3=CC=C(C=C3)O)O)O
• InChI: InChI=1S/C16H12O7/c1-22-15-10(19)6-9(18)11-12(20)13(21)14(23-16(11)15)7-2-4-8(17)5-3-7/h2-6,17-19,21H,1H3
• InChI Key: AZFYHRHUTXBGJS-UHFFFAOYSA-N
• Popularity: 40 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₂O₇
• Molecular Weight: 316.26 g/mol
• Exact Mass: 316.05830272 g/mol
• Topological Polar Surface Area (TPSA): 116.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.29
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• 8-methoxykaempferol
• 571-74-4
• Herbacetin 8-methyl ether
• 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-8-methoxychromen-4-one
• 3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-8-methoxy-4H-1-benzopyran-4-one
• 4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-8-methoxy-
• CHEBI:9131
• SCHEMBL1608916
• DTXSID00205715
• 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-8-methoxy-chromen-4-one
• LMPK12113150
• 3,5,7,4'-tetrahydroxy-8-methoxyflavone
• Q27108284
• 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-8-methoxy-4H-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9524	95.24%
Caco-2	+	0.5411	54.11%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6494	64.94%
OATP2B1 inhibitior	-	0.5291	52.91%
OATP1B1 inhibitior	+	0.8833	88.33%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.5811	58.11%
P-glycoprotein inhibitior	-	0.6800	68.00%
P-glycoprotein substrate	-	0.7642	76.42%
CYP3A4 substrate	+	0.5198	51.98%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	+	0.7348	73.48%
CYP2C9 inhibition	+	0.7560	75.60%
CYP2C19 inhibition	+	0.8648	86.48%
CYP2D6 inhibition	-	0.6993	69.93%
CYP1A2 inhibition	+	0.9218	92.18%
CYP2C8 inhibition	+	0.7760	77.60%
CYP inhibitory promiscuity	+	0.8546	85.46%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6176	61.76%
Eye corrosion	-	0.9767	97.67%
Eye irritation	+	0.8522	85.22%
Skin irritation	-	0.5841	58.41%
Skin corrosion	-	0.9319	93.19%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7347	73.47%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	-	0.5199	51.99%
skin sensitisation	-	0.9240	92.40%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.7371	73.71%
Acute Oral Toxicity (c)	III	0.7362	73.62%
Estrogen receptor binding	+	0.8711	87.11%
Androgen receptor binding	+	0.8196	81.96%
Thyroid receptor binding	+	0.5785	57.85%
Glucocorticoid receptor binding	+	0.8896	88.96%
Aromatase binding	+	0.8141	81.41%
PPAR gamma	+	0.7839	78.39%
Honey bee toxicity	-	0.8845	88.45%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.8321	83.21%

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	99.05%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.90%	94.00%
CHEMBL2581	P07339	Cathepsin D	92.84%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.04%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.23%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.97%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.62%	86.33%
CHEMBL242	Q92731	Estrogen receptor beta	89.62%	98.35%
CHEMBL3194	P02766	Transthyretin	87.14%	90.71%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	87.04%	95.64%
CHEMBL3401	O75469	Pregnane X receptor	86.93%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.04%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.82%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.45%	99.23%

Plants that contains it

• Ageratina gracilis
• Askidiosperma paniculatum
• Camellia japonica
• Crataegus monogyna
• Crataegus pinnatifida
• Crataegus sanguinea
• Daphne genkwa
• Lotus corniculatus
• Lotus dorycnium
• Randonia africana
• Rhodiola rosea
• Sedum alpestre
• Sorbus intermedia
• Zingiber officinale

Cross-Links

• PubChem: 5281698
• NPASS: NPC49901
• LOTUS: LTS0161576
• wikiData: Q27108284