(2S)-5,7-dihydroxy-2-methyl-6-(3-methylbut-2-enyl)-2-phenyl-3H-chromen-4-one

Details

• Internal ID: b27959be-2313-452a-90b4-21dbf8b0d0b7
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 6-prenylated flavans > 6-prenylated flavanones
• IUPAC Name: (2S)-5,7-dihydroxy-2-methyl-6-(3-methylbut-2-enyl)-2-phenyl-3H-chromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C2=C(C=C1O)OC(CC2=O)(C)C3=CC=CC=C3)O)C
• SMILES (Isomeric): CC(=CCC1=C(C2=C(C=C1O)O[C@](CC2=O)(C)C3=CC=CC=C3)O)C
• InChI: InChI=1S/C21H22O4/c1-13(2)9-10-15-16(22)11-18-19(20(15)24)17(23)12-21(3,25-18)14-7-5-4-6-8-14/h4-9,11,22,24H,10,12H2,1-3H3/t21-/m0/s1
• InChI Key: VVRRONQTBZDWOB-NRFANRHFSA-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: 4.90
• Atomic LogP (AlogP): 4.49
• 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	+	0.9877	98.77%
Caco-2	+	0.5613	56.13%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7125	71.25%
OATP2B1 inhibitior	-	0.5798	57.98%
OATP1B1 inhibitior	+	0.8705	87.05%
OATP1B3 inhibitior	+	0.9333	93.33%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9028	90.28%
P-glycoprotein inhibitior	-	0.4800	48.00%
P-glycoprotein substrate	-	0.8443	84.43%
CYP3A4 substrate	+	0.5102	51.02%
CYP2C9 substrate	-	0.7977	79.77%
CYP2D6 substrate	-	0.7912	79.12%
CYP3A4 inhibition	-	0.6106	61.06%
CYP2C9 inhibition	+	0.7949	79.49%
CYP2C19 inhibition	+	0.8513	85.13%
CYP2D6 inhibition	-	0.7989	79.89%
CYP1A2 inhibition	+	0.7248	72.48%
CYP2C8 inhibition	+	0.4769	47.69%
CYP inhibitory promiscuity	+	0.8528	85.28%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6542	65.42%
Eye corrosion	-	0.9917	99.17%
Eye irritation	+	0.7017	70.17%
Skin irritation	-	0.7416	74.16%
Skin corrosion	-	0.9205	92.05%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3940	39.40%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.7535	75.35%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.5232	52.32%
Acute Oral Toxicity (c)	III	0.3899	38.99%
Estrogen receptor binding	+	0.8738	87.38%
Androgen receptor binding	+	0.6524	65.24%
Thyroid receptor binding	+	0.5997	59.97%
Glucocorticoid receptor binding	+	0.7645	76.45%
Aromatase binding	+	0.7009	70.09%
PPAR gamma	+	0.9029	90.29%
Honey bee toxicity	-	0.9055	90.55%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9945	99.45%

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	99.76%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.65%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.12%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.54%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.46%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	88.53%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.24%	85.14%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.01%	94.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.92%	89.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.45%	93.99%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.14%	91.07%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.56%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.24%	99.23%

Plants that contains it

• Deguelia rariflora
• Garcinia pedunculata

Cross-Links

• PubChem: 162820524
• LOTUS: LTS0027681
• wikiData: Q105001803