7,8,3',4'-Tetrahydroxyflavone

Details

• Internal ID: bf5a62bf-97d4-4761-ad7a-1630f3e96bc3
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-7,8-dihydroxychromen-4-one
• SMILES (Canonical): C1=CC(=C(C=C1C2=CC(=O)C3=C(O2)C(=C(C=C3)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2=CC(=O)C3=C(O2)C(=C(C=C3)O)O)O)O
• InChI: InChI=1S/C15H10O6/c16-9-3-1-7(5-12(9)19)13-6-11(18)8-2-4-10(17)14(20)15(8)21-13/h1-6,16-17,19-20H
• InChI Key: ARYCMKPCDNHQCL-UHFFFAOYSA-N
• Popularity: 22 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₀O₆
• Molecular Weight: 286.24 g/mol
• Exact Mass: 286.04773803 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.28
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

• 3440-24-2
• 3',4',7,8-Tetrahydroxyflavone
• 2-(3,4-dihydroxyphenyl)-7,8-dihydroxy-4H-chromen-4-one
• 2-(3,4-dihydroxyphenyl)-7,8-dihydroxychromen-4-one
• CHEMBL222541
• 2-[3,4-bis(oxidanyl)phenyl]-7,8-bis(oxidanyl)chromen-4-one
• 7,8,3 inverted exclamation marka,4 inverted exclamation marka-Tetrahydroxyflavone
• SQH
• ST059620
• SCHEMBL35318
• DTXSID20350973
• CHEBI:125596
• HY-N8600
• 7,8,3'',4''-tetrahydroxyflavone
• BDBM50157547
• MFCD00017435
• AKOS024283046
• PD183059
• CS-0148693
• FT-0614178
• 2-(3,4-dihydroxyphenyl)-7,8-dihydroxy-chromen-4-one
• BRD-K58443469-001-01-0
• Q27216211
• 2-(3,4-dihydroxyphenyl)-7,8-dihydroxy-1-benzopyran-4-one
• 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-7,8-dihydroxy-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9569	95.69%
Caco-2	-	0.6995	69.95%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7742	77.42%
OATP2B1 inhibitior	-	0.5224	52.24%
OATP1B1 inhibitior	+	0.9553	95.53%
OATP1B3 inhibitior	+	0.9902	99.02%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8475	84.75%
P-glycoprotein inhibitior	-	0.9051	90.51%
P-glycoprotein substrate	-	0.8904	89.04%
CYP3A4 substrate	-	0.5411	54.11%
CYP2C9 substrate	-	0.8321	83.21%
CYP2D6 substrate	-	0.8118	81.18%
CYP3A4 inhibition	-	0.7054	70.54%
CYP2C9 inhibition	+	0.8949	89.49%
CYP2C19 inhibition	-	0.6965	69.65%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	+	0.9249	92.49%
CYP2C8 inhibition	+	0.5698	56.98%
CYP inhibitory promiscuity	-	0.5409	54.09%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5926	59.26%
Eye corrosion	-	0.9890	98.90%
Eye irritation	+	0.9623	96.23%
Skin irritation	+	0.6100	61.00%
Skin corrosion	-	0.9613	96.13%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8821	88.21%
Micronuclear	+	0.9400	94.00%
Hepatotoxicity	+	0.6575	65.75%
skin sensitisation	-	0.8006	80.06%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8539	85.39%
Acute Oral Toxicity (c)	II	0.7187	71.87%
Estrogen receptor binding	+	0.8737	87.37%
Androgen receptor binding	+	0.9256	92.56%
Thyroid receptor binding	+	0.5261	52.61%
Glucocorticoid receptor binding	+	0.9208	92.08%
Aromatase binding	+	0.8529	85.29%
PPAR gamma	+	0.8530	85.30%
Honey bee toxicity	-	0.8907	89.07%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9311	93.11%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2916	O14746	Telomerase reverse transcriptase	200 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.66%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.79%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.06%	99.15%
CHEMBL2581	P07339	Cathepsin D	93.53%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.50%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.65%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.01%	95.56%
CHEMBL3194	P02766	Transthyretin	88.26%	90.71%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	87.88%	98.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.78%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.24%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.46%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	81.29%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.55%	99.23%

Plants that contains it

• Acacia confusa

Cross-Links

• PubChem: 688798
• LOTUS: LTS0193878
• wikiData: Q27216211