5-Hydroxy-7-methoxy-6-C-prenylflavanone

Details

• Internal ID: b0e203ee-bdda-4ea4-a862-552e8a9e355e
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 6-prenylated flavans > 6-prenylated flavanones
• IUPAC Name: 5-hydroxy-7-methoxy-6-(3-methylbut-2-enyl)-2-phenyl-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C=C2C(=C1O)C(=O)CC(O2)C3=CC=CC=C3)OC)C
• SMILES (Isomeric): CC(=CCC1=C(C=C2C(=C1O)C(=O)CC(O2)C3=CC=CC=C3)OC)C
• InChI: InChI=1S/C21H22O4/c1-13(2)9-10-15-18(24-3)12-19-20(21(15)23)16(22)11-17(25-19)14-7-5-4-6-8-14/h4-9,12,17,23H,10-11H2,1-3H3
• InChI Key: SIGVEYBZDIDQLH-UHFFFAOYSA-N
• Popularity: 2 references 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): 55.80 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 4.62
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• CHEMBL1088927
• LMPK12140167
• 5-hydroxy-7-methoxy-6-prenylflavanone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9923	99.23%
Caco-2	+	0.5801	58.01%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8026	80.26%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8918	89.18%
OATP1B3 inhibitior	+	0.9299	92.99%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8963	89.63%
P-glycoprotein inhibitior	+	0.8145	81.45%
P-glycoprotein substrate	-	0.8095	80.95%
CYP3A4 substrate	+	0.5550	55.50%
CYP2C9 substrate	-	0.7977	79.77%
CYP2D6 substrate	-	0.7912	79.12%
CYP3A4 inhibition	-	0.7740	77.40%
CYP2C9 inhibition	+	0.8274	82.74%
CYP2C19 inhibition	+	0.9070	90.70%
CYP2D6 inhibition	-	0.6698	66.98%
CYP1A2 inhibition	+	0.7689	76.89%
CYP2C8 inhibition	+	0.5908	59.08%
CYP inhibitory promiscuity	+	0.8740	87.40%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9613	96.13%
Carcinogenicity (trinary)	Non-required	0.6937	69.37%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.6453	64.53%
Skin irritation	-	0.7861	78.61%
Skin corrosion	-	0.9609	96.09%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7343	73.43%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.8323	83.23%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.6530	65.30%
Acute Oral Toxicity (c)	III	0.5374	53.74%
Estrogen receptor binding	+	0.7674	76.74%
Androgen receptor binding	+	0.5832	58.32%
Thyroid receptor binding	+	0.5545	55.45%
Glucocorticoid receptor binding	+	0.7335	73.35%
Aromatase binding	+	0.5578	55.78%
PPAR gamma	+	0.9219	92.19%
Honey bee toxicity	-	0.8087	80.87%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9856	98.56%

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	99.40%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.87%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.46%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.17%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.87%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.31%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.89%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.82%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.20%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.65%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.17%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	84.09%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.40%	95.89%

Plants that contains it

• Eysenhardtia platycarpa

Cross-Links

• PubChem: 42607868
• LOTUS: LTS0030322
• wikiData: Q104399226