(2R)-5,7-dihydroxy-6-methyl-8-(3-methylbut-2-enyl)-2-phenyl-2,3-dihydrochromen-4-one

Details

• Internal ID: 40731ba4-9de4-4eb7-9bb0-fb4c9fd96363
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 8-prenylated flavans > 8-prenylated flavanones
• IUPAC Name: (2R)-5,7-dihydroxy-6-methyl-8-(3-methylbut-2-enyl)-2-phenyl-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC1=C(C(=C2C(=C1O)C(=O)CC(O2)C3=CC=CC=C3)CC=C(C)C)O
• SMILES (Isomeric): CC1=C(C(=C2C(=C1O)C(=O)C[C@@H](O2)C3=CC=CC=C3)CC=C(C)C)O
• InChI: InChI=1S/C21H22O4/c1-12(2)9-10-15-19(23)13(3)20(24)18-16(22)11-17(25-21(15)18)14-7-5-4-6-8-14/h4-9,17,23-24H,10-11H2,1-3H3/t17-/m1/s1
• InChI Key: CVIONCVYSLKMFU-QGZVFWFLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₄
• Molecular Weight: 338.40 g/mol
• Exact Mass: 338.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 4.62
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9825	98.25%
Caco-2	+	0.8522	85.22%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7222	72.22%
OATP2B1 inhibitior	-	0.7258	72.58%
OATP1B1 inhibitior	+	0.8251	82.51%
OATP1B3 inhibitior	+	0.9393	93.93%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7171	71.71%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.8661	86.61%
CYP3A4 substrate	+	0.5169	51.69%
CYP2C9 substrate	-	0.7977	79.77%
CYP2D6 substrate	-	0.7912	79.12%
CYP3A4 inhibition	-	0.5726	57.26%
CYP2C9 inhibition	+	0.8744	87.44%
CYP2C19 inhibition	+	0.8420	84.20%
CYP2D6 inhibition	-	0.6538	65.38%
CYP1A2 inhibition	+	0.8815	88.15%
CYP2C8 inhibition	-	0.6046	60.46%
CYP inhibitory promiscuity	+	0.9017	90.17%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6617	66.17%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.5181	51.81%
Skin irritation	-	0.7417	74.17%
Skin corrosion	-	0.9379	93.79%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3793	37.93%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.7552	75.52%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.6788	67.88%
Acute Oral Toxicity (c)	III	0.4893	48.93%
Estrogen receptor binding	+	0.7930	79.30%
Androgen receptor binding	+	0.5648	56.48%
Thyroid receptor binding	+	0.5811	58.11%
Glucocorticoid receptor binding	+	0.7072	70.72%
Aromatase binding	-	0.7414	74.14%
PPAR gamma	+	0.9061	90.61%
Honey bee toxicity	-	0.9041	90.41%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9903	99.03%

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	98.30%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.13%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.69%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	93.10%	90.17%
CHEMBL3401	O75469	Pregnane X receptor	92.43%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.41%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.84%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.02%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.95%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	81.21%	91.49%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	80.68%	96.37%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.55%	97.09%

Plants that contains it

• Eysenhardtia platycarpa

Cross-Links

• PubChem: 162846661
• LOTUS: LTS0155118
• wikiData: Q104970761