(2S)-6-methoxy-8,8-dimethyl-2-phenyl-2,3-dihydropyrano[2,3-h]chromen-4-one

Details

• Internal ID: 037dd55f-e409-44fa-8c12-a34b27a1eaa9
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Pyranoflavonoids
• IUPAC Name: (2S)-6-methoxy-8,8-dimethyl-2-phenyl-2,3-dihydropyrano[2,3-h]chromen-4-one
• SMILES (Canonical): CC1(C=CC2=C3C(=CC(=C2O1)OC)C(=O)CC(O3)C4=CC=CC=C4)C
• SMILES (Isomeric): CC1(C=CC2=C3C(=CC(=C2O1)OC)C(=O)C[C@H](O3)C4=CC=CC=C4)C
• InChI: InChI=1S/C21H20O4/c1-21(2)10-9-14-19-15(11-18(23-3)20(14)25-21)16(22)12-17(24-19)13-7-5-4-6-8-13/h4-11,17H,12H2,1-3H3/t17-/m0/s1
• InChI Key: NNVQEIPRIPRHHU-KRWDZBQOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₄
• Molecular Weight: 336.40 g/mol
• Exact Mass: 336.13615911 g/mol
• Topological Polar Surface Area (TPSA): 44.80 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 4.59
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9934	99.34%
Caco-2	+	0.8091	80.91%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7697	76.97%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.9169	91.69%
OATP1B3 inhibitior	+	0.9782	97.82%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9227	92.27%
P-glycoprotein inhibitior	+	0.6876	68.76%
P-glycoprotein substrate	-	0.7525	75.25%
CYP3A4 substrate	+	0.6124	61.24%
CYP2C9 substrate	-	0.8027	80.27%
CYP2D6 substrate	-	0.7486	74.86%
CYP3A4 inhibition	+	0.8724	87.24%
CYP2C9 inhibition	-	0.8060	80.60%
CYP2C19 inhibition	+	0.8382	83.82%
CYP2D6 inhibition	-	0.6811	68.11%
CYP1A2 inhibition	-	0.5756	57.56%
CYP2C8 inhibition	+	0.4489	44.89%
CYP inhibitory promiscuity	+	0.7091	70.91%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Danger	0.4539	45.39%
Eye corrosion	-	0.9823	98.23%
Eye irritation	-	0.7666	76.66%
Skin irritation	-	0.8148	81.48%
Skin corrosion	-	0.9709	97.09%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6681	66.81%
Micronuclear	+	0.5559	55.59%
Hepatotoxicity	-	0.5207	52.07%
skin sensitisation	-	0.7935	79.35%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	+	0.6923	69.23%
Acute Oral Toxicity (c)	III	0.5386	53.86%
Estrogen receptor binding	+	0.8544	85.44%
Androgen receptor binding	+	0.5764	57.64%
Thyroid receptor binding	+	0.7367	73.67%
Glucocorticoid receptor binding	+	0.8306	83.06%
Aromatase binding	-	0.6215	62.15%
PPAR gamma	+	0.7742	77.42%
Honey bee toxicity	-	0.7527	75.27%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9083	90.83%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.01%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.87%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.06%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.21%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.91%	86.33%
CHEMBL2581	P07339	Cathepsin D	91.72%	98.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.46%	97.14%
CHEMBL2535	P11166	Glucose transporter	87.14%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.11%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.25%	99.23%
CHEMBL221	P23219	Cyclooxygenase-1	83.23%	90.17%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.32%	95.71%
CHEMBL5028	O14672	ADAM10	82.05%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.64%	97.09%

Plants that contains it

• Lonchocarpus subglaucescens

Cross-Links

• PubChem: 163085146
• LOTUS: LTS0053028
• wikiData: Q105182335