(2R,3R)-3,5,7,8-Tetrahydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one

Details

• Internal ID: 992b0b15-d37c-474e-9d3a-1fd60ea7b155
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavanones > Flavanonols
• IUPAC Name: (2R,3R)-3,5,7,8-tetrahydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2C(C(=O)C3=C(O2)C(=C(C=C3O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1[C@@H]2[C@H](C(=O)C3=C(O2)C(=C(C=C3O)O)O)O)O
• InChI: InChI=1S/C15H12O7/c16-7-3-1-6(2-4-7)14-13(21)12(20)10-8(17)5-9(18)11(19)15(10)22-14/h1-5,13-14,16-19,21H/t13-,14+/m0/s1
• InChI Key: YOTJHIQKUFOLIM-UONOGXRCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₇
• Molecular Weight: 304.25 g/mol
• Exact Mass: 304.05830272 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.19
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 1

Synonyms

• (2R,3R)-3,5,7,8-tetrahydroxy-2-(4-hydroxyphenyl)chroman-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9071	90.71%
Caco-2	-	0.8815	88.15%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.5892	58.92%
OATP2B1 inhibitior	-	0.6855	68.55%
OATP1B1 inhibitior	+	0.7821	78.21%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9137	91.37%
P-glycoprotein inhibitior	-	0.8772	87.72%
P-glycoprotein substrate	-	0.9483	94.83%
CYP3A4 substrate	-	0.5211	52.11%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7991	79.91%
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	-	0.6383	63.83%
CYP inhibitory promiscuity	+	0.5822	58.22%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6750	67.50%
Eye corrosion	-	0.9905	99.05%
Eye irritation	+	0.9463	94.63%
Skin irritation	+	0.5835	58.35%
Skin corrosion	-	0.9397	93.97%
Ames mutagenesis	-	0.5454	54.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.8131	81.31%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.7447	74.47%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	II	0.7348	73.48%
Estrogen receptor binding	-	0.5179	51.79%
Androgen receptor binding	+	0.7494	74.94%
Thyroid receptor binding	+	0.6141	61.41%
Glucocorticoid receptor binding	+	0.8265	82.65%
Aromatase binding	+	0.6827	68.27%
PPAR gamma	+	0.6519	65.19%
Honey bee toxicity	-	0.9056	90.56%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
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	98.80%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	93.98%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.61%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.28%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	87.40%	94.73%
CHEMBL3194	P02766	Transthyretin	85.84%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.18%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.76%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.52%	97.09%
CHEMBL2581	P07339	Cathepsin D	82.66%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.19%	94.00%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	81.82%	90.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.13%	86.33%

Plants that contains it

• Calluna vulgaris

Cross-Links

• PubChem: 468911
• LOTUS: LTS0266555
• wikiData: Q105351515