(2R,3R)-3,7,8-trihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one

Details

• Internal ID: cbe47bc4-d598-4fb5-89a8-8f1098100057
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavanones > Flavanonols
• IUPAC Name: (2R,3R)-3,7,8-trihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2C(C(=O)C3=C(O2)C(=C(C=C3)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1[C@@H]2[C@H](C(=O)C3=C(O2)C(=C(C=C3)O)O)O)O
• InChI: InChI=1S/C15H12O6/c16-8-3-1-7(2-4-8)14-13(20)11(18)9-5-6-10(17)12(19)15(9)21-14/h1-6,13-14,16-17,19-20H/t13-,14+/m0/s1
• InChI Key: WVRVTLSVEGPDPC-UONOGXRCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₆
• Molecular Weight: 288.25 g/mol
• Exact Mass: 288.06338810 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.48
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9569	95.69%
Caco-2	-	0.8948	89.48%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7742	77.42%
OATP2B1 inhibitior	-	0.7008	70.08%
OATP1B1 inhibitior	+	0.7423	74.23%
OATP1B3 inhibitior	+	0.9902	99.02%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8950	89.50%
P-glycoprotein inhibitior	-	0.8843	88.43%
P-glycoprotein substrate	-	0.9442	94.42%
CYP3A4 substrate	-	0.5189	51.89%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7351	73.51%
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	-	0.7135	71.35%
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	+	0.9468	94.68%
Skin irritation	+	0.6100	61.00%
Skin corrosion	-	0.9613	96.13%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8899	88.99%
Micronuclear	+	0.9400	94.00%
Hepatotoxicity	+	0.5500	55.00%
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	+	0.6490	64.90%
Acute Oral Toxicity (c)	II	0.7187	71.87%
Estrogen receptor binding	-	0.5809	58.09%
Androgen receptor binding	+	0.6488	64.88%
Thyroid receptor binding	+	0.6436	64.36%
Glucocorticoid receptor binding	+	0.8259	82.59%
Aromatase binding	+	0.6808	68.08%
PPAR gamma	+	0.5965	59.65%
Honey bee toxicity	-	0.8870	88.70%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9311	93.11%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.53%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.22%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.68%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.63%	89.00%
CHEMBL2581	P07339	Cathepsin D	88.52%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.66%	99.23%
CHEMBL242	Q92731	Estrogen receptor beta	85.50%	98.35%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.16%	97.09%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	84.57%	90.93%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.04%	99.15%
CHEMBL3194	P02766	Transthyretin	82.98%	90.71%

Plants that contains it

• Acacia auriculiformis

Cross-Links

• PubChem: 101382379
• LOTUS: LTS0072228
• wikiData: Q105313719