(2S)-7-hydroxy-8-(3-methylbut-2-enyl)-2-phenyl-2,3-dihydrochromen-4-one

Details

• Internal ID: f630b45e-be0b-49d9-9094-1ae964eb1d0c
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 8-prenylated flavans > 8-prenylated flavanones
• IUPAC Name: (2S)-7-hydroxy-8-(3-methylbut-2-enyl)-2-phenyl-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C=CC2=C1OC(CC2=O)C3=CC=CC=C3)O)C
• SMILES (Isomeric): CC(=CCC1=C(C=CC2=C1O[C@@H](CC2=O)C3=CC=CC=C3)O)C
• InChI: InChI=1S/C20H20O3/c1-13(2)8-9-15-17(21)11-10-16-18(22)12-19(23-20(15)16)14-6-4-3-5-7-14/h3-8,10-11,19,21H,9,12H2,1-2H3/t19-/m0/s1
• InChI Key: ZBNBGEUTJNZRKT-IBGZPJMESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₃
• Molecular Weight: 308.40 g/mol
• Exact Mass: 308.14124450 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.61
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7724	77.24%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8532	85.32%
OATP2B1 inhibitior	-	0.8650	86.50%
OATP1B1 inhibitior	+	0.8873	88.73%
OATP1B3 inhibitior	+	0.9646	96.46%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7613	76.13%
P-glycoprotein inhibitior	-	0.4724	47.24%
P-glycoprotein substrate	-	0.8483	84.83%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.8006	80.06%
CYP2D6 substrate	-	0.7235	72.35%
CYP3A4 inhibition	-	0.7665	76.65%
CYP2C9 inhibition	+	0.8286	82.86%
CYP2C19 inhibition	+	0.8939	89.39%
CYP2D6 inhibition	-	0.8453	84.53%
CYP1A2 inhibition	+	0.7775	77.75%
CYP2C8 inhibition	-	0.7435	74.35%
CYP inhibitory promiscuity	+	0.8509	85.09%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9613	96.13%
Carcinogenicity (trinary)	Non-required	0.6725	67.25%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.7154	71.54%
Skin irritation	-	0.7166	71.66%
Skin corrosion	-	0.9399	93.99%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4076	40.76%
Micronuclear	-	0.5241	52.41%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.6372	63.72%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.5418	54.18%
Acute Oral Toxicity (c)	III	0.6133	61.33%
Estrogen receptor binding	+	0.8614	86.14%
Androgen receptor binding	+	0.6996	69.96%
Thyroid receptor binding	+	0.6533	65.33%
Glucocorticoid receptor binding	+	0.5625	56.25%
Aromatase binding	-	0.5249	52.49%
PPAR gamma	+	0.8105	81.05%
Honey bee toxicity	-	0.8752	87.52%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9884	98.84%

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	98.96%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.36%	91.49%
CHEMBL2581	P07339	Cathepsin D	96.60%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.76%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	93.99%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.69%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.02%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.88%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	86.88%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.38%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.43%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.48%	89.00%

Plants that contains it

• Glycyrrhiza pallidiflora

Cross-Links

• PubChem: 163011623
• LOTUS: LTS0167741
• wikiData: Q105370713