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

Details

• Internal ID: 3623682c-33a7-49ad-99f9-0dbebbc664c8
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavanones > Flavanonols
• IUPAC Name: (2R,3R)-3,5,7-trihydroxy-6,8-dimethyl-2-phenyl-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC1=C(C(=C2C(=C1O)C(=O)C(C(O2)C3=CC=CC=C3)O)C)O
• SMILES (Isomeric): CC1=C(C(=C2C(=C1O)C(=O)[C@@H]([C@H](O2)C3=CC=CC=C3)O)C)O
• InChI: InChI=1S/C17H16O5/c1-8-12(18)9(2)16-11(13(8)19)14(20)15(21)17(22-16)10-6-4-3-5-7-10/h3-7,15,17-19,21H,1-2H3/t15-,17+/m0/s1
• InChI Key: HDEMWSJTNCFIGR-DOTOQJQBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₆O₅
• Molecular Weight: 300.30 g/mol
• Exact Mass: 300.09977361 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.39
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• SCHEMBL10013321
• BDBM50482881

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9513	95.13%
Caco-2	-	0.8055	80.55%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7075	70.75%
OATP2B1 inhibitior	-	0.7205	72.05%
OATP1B1 inhibitior	+	0.7768	77.68%
OATP1B3 inhibitior	+	0.7955	79.55%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8137	81.37%
P-glycoprotein inhibitior	-	0.6688	66.88%
P-glycoprotein substrate	-	0.9446	94.46%
CYP3A4 substrate	-	0.5600	56.00%
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	-	0.5839	58.39%
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	+	0.6073	60.73%
Skin irritation	-	0.5565	55.65%
Skin corrosion	-	0.9210	92.10%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7178	71.78%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.8507	85.07%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.6385	63.85%
Acute Oral Toxicity (c)	III	0.5964	59.64%
Estrogen receptor binding	+	0.5473	54.73%
Androgen receptor binding	-	0.4932	49.32%
Thyroid receptor binding	+	0.5565	55.65%
Glucocorticoid receptor binding	+	0.7068	70.68%
Aromatase binding	-	0.5930	59.30%
PPAR gamma	+	0.5525	55.25%
Honey bee toxicity	-	0.9581	95.81%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
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	97.23%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.77%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.01%	99.23%
CHEMBL2581	P07339	Cathepsin D	91.01%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.37%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.00%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	86.53%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.99%	86.33%

Plants that contains it

• Syzygium nervosum

Cross-Links

• PubChem: 49831444
• LOTUS: LTS0136442
• wikiData: Q105026297