3,5,6,7,8-Pentahydroxy-2-phenyl-4H-1-benzopyran-4-one

Details

• Internal ID: 587c8ab8-f5a4-44f2-9631-a70c0a33ebc0
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > Flavonols
• IUPAC Name: 3,5,6,7,8-pentahydroxy-2-phenylchromen-4-one
• SMILES (Canonical): C1=CC=C(C=C1)C2=C(C(=O)C3=C(C(=C(C(=C3O2)O)O)O)O)O
• SMILES (Isomeric): C1=CC=C(C=C1)C2=C(C(=O)C3=C(C(=C(C(=C3O2)O)O)O)O)O
• InChI: InChI=1S/C15H10O7/c16-8-7-9(17)12(20)14(6-4-2-1-3-5-6)22-15(7)13(21)11(19)10(8)18/h1-5,16,18-21H
• InChI Key: RNKSNQNKTRGJSZ-UHFFFAOYSA-N
• Popularity: 134 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₀O₇
• Molecular Weight: 302.23 g/mol
• Exact Mass: 302.04265265 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 1.99
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 1

Synonyms

• Pentahydroxyflavone
• 3,5,6,7,8-Pentahydroxy-2-phenyl-4H-1-benzopyran-4-one
• SCHEMBL316143
• DTXSID80648686
• 3,5,6,7,8-Pentahydroxy-2-phenyl-4H-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9071	90.71%
Caco-2	-	0.9582	95.82%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5892	58.92%
OATP2B1 inhibitior	-	0.6621	66.21%
OATP1B1 inhibitior	+	0.9284	92.84%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	+	0.6600	66.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8902	89.02%
P-glycoprotein inhibitior	-	0.8619	86.19%
P-glycoprotein substrate	-	0.9261	92.61%
CYP3A4 substrate	-	0.6242	62.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8553	85.53%
CYP3A4 inhibition	+	0.6951	69.51%
CYP2C9 inhibition	-	0.5823	58.23%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9287	92.87%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	-	0.5613	56.13%
CYP inhibitory promiscuity	+	0.5822	58.22%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6750	67.50%
Eye corrosion	-	0.9905	99.05%
Eye irritation	+	0.9233	92.33%
Skin irritation	+	0.5835	58.35%
Skin corrosion	-	0.9397	93.97%
Ames mutagenesis	+	0.5063	50.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.8519	85.19%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.7447	74.47%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.4767	47.67%
Acute Oral Toxicity (c)	II	0.7348	73.48%
Estrogen receptor binding	+	0.6489	64.89%
Androgen receptor binding	+	0.6172	61.72%
Thyroid receptor binding	+	0.5521	55.21%
Glucocorticoid receptor binding	+	0.8695	86.95%
Aromatase binding	+	0.7894	78.94%
PPAR gamma	+	0.8979	89.79%
Honey bee toxicity	-	0.8837	88.37%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9124	91.24%

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	98.20%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.30%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.31%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.13%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.25%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.22%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.90%	99.23%
CHEMBL262	P49841	Glycogen synthase kinase-3 beta	84.97%	95.72%
CHEMBL3959	P16083	Quinone reductase 2	84.84%	89.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.77%	94.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 25087106
• LOTUS: LTS0154580
• wikiData: Q82561415