(2R,3R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-6,8-dimethyl-2,3-dihydrochromen-4-one

Details

• Internal ID: 640633b7-0efc-4148-9cc1-716dbb44a93c
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavanones > Flavanonols
• IUPAC Name: (2R,3R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-6,8-dimethyl-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC1=C(C(=C2C(=C1O)C(=O)C(C(O2)C3=CC=C(C=C3)O)O)C)O
• SMILES (Isomeric): CC1=C(C(=C2C(=C1O)C(=O)[C@@H]([C@H](O2)C3=CC=C(C=C3)O)O)C)O
• InChI: InChI=1S/C17H16O6/c1-7-12(19)8(2)16-11(13(7)20)14(21)15(22)17(23-16)9-3-5-10(18)6-4-9/h3-6,15,17-20,22H,1-2H3/t15-,17+/m0/s1
• InChI Key: IHXGBCCXWBTPRR-DOTOQJQBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₆O₆
• Molecular Weight: 316.30 g/mol
• Exact Mass: 316.09468823 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.10
• 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	+	0.9513	95.13%
Caco-2	-	0.6802	68.02%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7075	70.75%
OATP2B1 inhibitior	-	0.7015	70.15%
OATP1B1 inhibitior	-	0.3380	33.80%
OATP1B3 inhibitior	+	0.7955	79.55%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.6787	67.87%
P-glycoprotein inhibitior	-	0.7806	78.06%
P-glycoprotein substrate	-	0.9189	91.89%
CYP3A4 substrate	+	0.5106	51.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8042	80.42%
CYP3A4 inhibition	+	0.7483	74.83%
CYP2C9 inhibition	+	0.7430	74.30%
CYP2C19 inhibition	+	0.5485	54.85%
CYP2D6 inhibition	-	0.8756	87.56%
CYP1A2 inhibition	+	0.9295	92.95%
CYP2C8 inhibition	-	0.5817	58.17%
CYP inhibitory promiscuity	+	0.7700	77.00%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6979	69.79%
Eye corrosion	-	0.9873	98.73%
Eye irritation	+	0.7153	71.53%
Skin irritation	-	0.5565	55.65%
Skin corrosion	-	0.9210	92.10%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6826	68.26%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.8507	85.07%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.5690	56.90%
Acute Oral Toxicity (c)	III	0.5964	59.64%
Estrogen receptor binding	+	0.7229	72.29%
Androgen receptor binding	+	0.6461	64.61%
Thyroid receptor binding	+	0.6906	69.06%
Glucocorticoid receptor binding	+	0.7854	78.54%
Aromatase binding	+	0.5703	57.03%
PPAR gamma	+	0.5789	57.89%
Honey bee toxicity	-	0.9394	93.94%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9197	91.97%

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	96.13%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.43%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.85%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.49%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.21%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.31%	91.11%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	88.06%	90.93%
CHEMBL3401	O75469	Pregnane X receptor	87.75%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.82%	97.09%

Plants that contains it

• Wikstroemia canescens

Cross-Links

• PubChem: 46831049
• LOTUS: LTS0225087
• wikiData: Q105113299