(2R)-5,8-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one

Details

• Internal ID: a81839ae-1f16-46bf-b4c5-15593e7062f0
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavanones
• IUPAC Name: (2R)-5,8-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1C(OC2=C(C=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O
• SMILES (Isomeric): C1[C@@H](OC2=C(C=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O
• InChI: InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)14-10(17)5-6-11(18)15(14)20-13/h1-6,13,16-18H,7H2/t13-/m1/s1
• InChI Key: SMRHIFAZRRVAQZ-CYBMUJFWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₅
• Molecular Weight: 272.25 g/mol
• Exact Mass: 272.06847348 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.51
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9619	96.19%
Caco-2	-	0.6828	68.28%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7907	79.07%
OATP2B1 inhibitior	-	0.7296	72.96%
OATP1B1 inhibitior	+	0.9219	92.19%
OATP1B3 inhibitior	+	0.9789	97.89%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8825	88.25%
P-glycoprotein inhibitior	-	0.9414	94.14%
P-glycoprotein substrate	-	0.9577	95.77%
CYP3A4 substrate	-	0.5669	56.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7429	74.29%
CYP3A4 inhibition	-	0.5899	58.99%
CYP2C9 inhibition	+	0.9625	96.25%
CYP2C19 inhibition	+	0.7847	78.47%
CYP2D6 inhibition	-	0.7735	77.35%
CYP1A2 inhibition	+	0.8794	87.94%
CYP2C8 inhibition	-	0.8080	80.80%
CYP inhibitory promiscuity	+	0.5417	54.17%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5290	52.90%
Eye corrosion	-	0.9901	99.01%
Eye irritation	+	0.8632	86.32%
Skin irritation	+	0.5071	50.71%
Skin corrosion	-	0.9673	96.73%
Ames mutagenesis	+	0.6646	66.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.8294	82.94%
Micronuclear	+	0.8259	82.59%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.8601	86.01%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.7233	72.33%
Acute Oral Toxicity (c)	II	0.4011	40.11%
Estrogen receptor binding	+	0.6844	68.44%
Androgen receptor binding	+	0.7212	72.12%
Thyroid receptor binding	+	0.6126	61.26%
Glucocorticoid receptor binding	+	0.7422	74.22%
Aromatase binding	+	0.6798	67.98%
PPAR gamma	+	0.8350	83.50%
Honey bee toxicity	-	0.8651	86.51%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.7636	76.36%

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	97.47%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.74%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.59%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.40%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.45%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.62%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.75%	89.00%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	82.98%	85.11%
CHEMBL2581	P07339	Cathepsin D	81.51%	98.95%

Plants that contains it

• Artemisia campestris
• Spinacia oleracea

Cross-Links

• PubChem: 162950933
• LOTUS: LTS0271058
• wikiData: Q105256116