(2R,3S)-3,5,7-trihydroxy-6-(3-methylbut-2-enyl)-2-phenyl-2,3-dihydrochromen-4-one

Details

• Internal ID: 8c16161f-cfff-4b5d-96e1-2b721405ebe9
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 6-prenylated flavans > 6-prenylated flavanones
• IUPAC Name: (2R,3S)-3,5,7-trihydroxy-6-(3-methylbut-2-enyl)-2-phenyl-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C2=C(C=C1O)OC(C(C2=O)O)C3=CC=CC=C3)O)C
• SMILES (Isomeric): CC(=CCC1=C(C2=C(C=C1O)O[C@@H]([C@@H](C2=O)O)C3=CC=CC=C3)O)C
• InChI: InChI=1S/C20H20O5/c1-11(2)8-9-13-14(21)10-15-16(17(13)22)18(23)19(24)20(25-15)12-6-4-3-5-7-12/h3-8,10,19-22,24H,9H2,1-2H3/t19-,20-/m1/s1
• InChI Key: JSHJOTDLYIHRKJ-WOJBJXKFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₅
• Molecular Weight: 340.40 g/mol
• Exact Mass: 340.13107373 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.28
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9873	98.73%
Caco-2	-	0.7668	76.68%
Blood Brain Barrier	-	0.5879	58.79%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6291	62.91%
OATP2B1 inhibitior	-	0.5845	58.45%
OATP1B1 inhibitior	+	0.8484	84.84%
OATP1B3 inhibitior	+	0.9248	92.48%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6783	67.83%
P-glycoprotein inhibitior	+	0.5863	58.63%
P-glycoprotein substrate	-	0.9000	90.00%
CYP3A4 substrate	-	0.5143	51.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7858	78.58%
CYP3A4 inhibition	-	0.5487	54.87%
CYP2C9 inhibition	+	0.9405	94.05%
CYP2C19 inhibition	+	0.8923	89.23%
CYP2D6 inhibition	-	0.6681	66.81%
CYP1A2 inhibition	+	0.8413	84.13%
CYP2C8 inhibition	-	0.5610	56.10%
CYP inhibitory promiscuity	+	0.9319	93.19%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7089	70.89%
Eye corrosion	-	0.9895	98.95%
Eye irritation	+	0.5875	58.75%
Skin irritation	-	0.7040	70.40%
Skin corrosion	-	0.9092	90.92%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3740	37.40%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.7070	70.70%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.5966	59.66%
Acute Oral Toxicity (c)	III	0.6133	61.33%
Estrogen receptor binding	+	0.7409	74.09%
Androgen receptor binding	+	0.6139	61.39%
Thyroid receptor binding	+	0.6031	60.31%
Glucocorticoid receptor binding	+	0.8496	84.96%
Aromatase binding	+	0.6444	64.44%
PPAR gamma	+	0.8732	87.32%
Honey bee toxicity	-	0.9153	91.53%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9923	99.23%

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	99.16%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.76%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	94.59%	94.73%
CHEMBL2581	P07339	Cathepsin D	93.70%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.96%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.45%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.73%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.19%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.15%	99.23%

Plants that contains it

• Flourensia riparia
• Glycyrrhiza lepidota
• Helichrysum thapsus

Cross-Links

• PubChem: 162984698
• LOTUS: LTS0219697
• wikiData: Q105134352