4,8-Dihydroxy-2H-chromen-2-one

Details

• Internal ID: d7ff9a13-a9a8-4404-a945-b6e9e3ca6f4e
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Hydroxycoumarins > 4-hydroxycoumarins
• IUPAC Name: 4,8-dihydroxychromen-2-one
• SMILES (Canonical): C1=CC2=C(C(=C1)O)OC(=O)C=C2O
• SMILES (Isomeric): C1=CC2=C(C(=C1)O)OC(=O)C=C2O
• InChI: InChI=1S/C9H6O4/c10-6-3-1-2-5-7(11)4-8(12)13-9(5)6/h1-4,10-11H
• InChI Key: YBGKGTOOPNQOKH-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₆O₄
• Molecular Weight: 178.14 g/mol
• Exact Mass: 178.02660867 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.20
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 4,8-Dihydroxy-2H-chromen-2-one
• 106754-20-5
• 4,8-dihydroxychromen-2-one
• AKOS006290013
• AC-5538
• CS-0440708

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9547	95.47%
Caco-2	+	0.5149	51.49%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	+	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6065	60.65%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9541	95.41%
OATP1B3 inhibitior	+	0.9492	94.92%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9240	92.40%
P-glycoprotein inhibitior	-	0.9626	96.26%
P-glycoprotein substrate	-	0.9655	96.55%
CYP3A4 substrate	-	0.6358	63.58%
CYP2C9 substrate	-	0.5385	53.85%
CYP2D6 substrate	-	0.8764	87.64%
CYP3A4 inhibition	-	0.7176	71.76%
CYP2C9 inhibition	-	0.7585	75.85%
CYP2C19 inhibition	-	0.9060	90.60%
CYP2D6 inhibition	-	0.9440	94.40%
CYP1A2 inhibition	+	0.6498	64.98%
CYP2C8 inhibition	-	0.8748	87.48%
CYP inhibitory promiscuity	-	0.8256	82.56%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5209	52.09%
Eye corrosion	-	0.9696	96.96%
Eye irritation	+	0.9838	98.38%
Skin irritation	+	0.6323	63.23%
Skin corrosion	-	0.9843	98.43%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8615	86.15%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.8368	83.68%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.7270	72.70%
Acute Oral Toxicity (c)	III	0.5246	52.46%
Estrogen receptor binding	+	0.6563	65.63%
Androgen receptor binding	+	0.7422	74.22%
Thyroid receptor binding	-	0.5764	57.64%
Glucocorticoid receptor binding	+	0.7314	73.14%
Aromatase binding	+	0.5692	56.92%
PPAR gamma	+	0.8078	80.78%
Honey bee toxicity	-	0.9403	94.03%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.8635	86.35%

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	97.35%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.33%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.79%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.96%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	89.59%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.75%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.34%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.75%	94.00%
CHEMBL2535	P11166	Glucose transporter	82.70%	98.75%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.68%	93.99%
CHEMBL1951	P21397	Monoamine oxidase A	81.46%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.04%	86.33%

Plants that contains it

• Cicer arietinum
• Daphne odora
• Daphne tangutica
• Euphorbia lathyris
• Stellera chamaejasme

Cross-Links

• PubChem: 54719604
• NPASS: NPC74729
• LOTUS: LTS0032046
• wikiData: Q105345816