5,2',5'-Trihydroxyflavone

Details

• Internal ID: 9641ffcf-cfc1-496d-9356-35ff469e3dd6
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones
• IUPAC Name: 2-(2,5-dihydroxyphenyl)-5-hydroxychromen-4-one
• SMILES (Canonical): C1=CC(=C2C(=C1)OC(=CC2=O)C3=C(C=CC(=C3)O)O)O
• SMILES (Isomeric): C1=CC(=C2C(=C1)OC(=CC2=O)C3=C(C=CC(=C3)O)O)O
• InChI: InChI=1S/C15H10O5/c16-8-4-5-10(17)9(6-8)14-7-12(19)15-11(18)2-1-3-13(15)20-14/h1-7,16-18H
• InChI Key: NAEHVPAKHDOTSP-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₀O₅
• Molecular Weight: 270.24 g/mol
• Exact Mass: 270.05282342 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.58
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• 5,2',5'-Trihydroxyflavon
• CHEBI:196246
• LMPK12110088
• 2-(2,5-dihydroxyphenyl)-5-hydroxychromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9853	98.53%
Caco-2	+	0.5476	54.76%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8516	85.16%
OATP2B1 inhibitior	-	0.5536	55.36%
OATP1B1 inhibitior	+	0.9053	90.53%
OATP1B3 inhibitior	+	0.9268	92.68%
MATE1 inhibitior	+	0.6600	66.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8039	80.39%
P-glycoprotein inhibitior	-	0.8516	85.16%
P-glycoprotein substrate	-	0.8468	84.68%
CYP3A4 substrate	-	0.5230	52.30%
CYP2C9 substrate	-	0.6443	64.43%
CYP2D6 substrate	-	0.8503	85.03%
CYP3A4 inhibition	-	0.6261	62.61%
CYP2C9 inhibition	+	0.9757	97.57%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	-	0.9199	91.99%
CYP1A2 inhibition	+	0.9108	91.08%
CYP2C8 inhibition	-	0.5642	56.42%
CYP inhibitory promiscuity	+	0.6929	69.29%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9613	96.13%
Carcinogenicity (trinary)	Non-required	0.6163	61.63%
Eye corrosion	-	0.9915	99.15%
Eye irritation	+	0.9816	98.16%
Skin irritation	+	0.6467	64.67%
Skin corrosion	-	0.9880	98.80%
Ames mutagenesis	+	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9145	91.45%
Micronuclear	+	0.9700	97.00%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.8894	88.94%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.5614	56.14%
Acute Oral Toxicity (c)	II	0.5629	56.29%
Estrogen receptor binding	+	0.9538	95.38%
Androgen receptor binding	+	0.8681	86.81%
Thyroid receptor binding	+	0.7486	74.86%
Glucocorticoid receptor binding	+	0.9160	91.60%
Aromatase binding	+	0.8685	86.85%
PPAR gamma	+	0.8982	89.82%
Honey bee toxicity	-	0.8845	88.45%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9385	93.85%

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	97.29%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.15%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.01%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.46%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.33%	99.15%
CHEMBL3194	P02766	Transthyretin	91.71%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	90.15%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	87.47%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.16%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.56%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.46%	94.00%
CHEMBL2535	P11166	Glucose transporter	82.89%	98.75%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.64%	90.71%

Plants that contains it

• Primula pulverulenta

Cross-Links

• PubChem: 14213592
• LOTUS: LTS0044233
• wikiData: Q105176189