5-Hydroxy-7-[(4-methoxyphenyl)methyl]-2,2-dimethyl-7,8-dihydropyrano[3,2-g]chromen-6-one

Details

• Internal ID: a09c0714-5089-4b54-bf41-52cb2763d9f8
• Taxonomy: Phenylpropanoids and polyketides > Homoisoflavonoids > Homoisoflavans > Homoisoflavanones
• IUPAC Name: 5-hydroxy-7-[(4-methoxyphenyl)methyl]-2,2-dimethyl-7,8-dihydropyrano[3,2-g]chromen-6-one
• SMILES (Canonical): CC1(C=CC2=C(C3=C(C=C2O1)OCC(C3=O)CC4=CC=C(C=C4)OC)O)C
• SMILES (Isomeric): CC1(C=CC2=C(C3=C(C=C2O1)OCC(C3=O)CC4=CC=C(C=C4)OC)O)C
• InChI: InChI=1S/C22H22O5/c1-22(2)9-8-16-17(27-22)11-18-19(21(16)24)20(23)14(12-26-18)10-13-4-6-15(25-3)7-5-13/h4-9,11,14,24H,10,12H2,1-3H3
• InChI Key: WHASMSGSLODBRS-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₅
• Molecular Weight: 366.40 g/mol
• Exact Mass: 366.14672380 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.02
• H-Bond Acceptor: 5
• 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	+	0.9843	98.43%
Caco-2	+	0.8085	80.85%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8330	83.30%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9156	91.56%
OATP1B3 inhibitior	+	0.9557	95.57%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9855	98.55%
P-glycoprotein inhibitior	+	0.7242	72.42%
P-glycoprotein substrate	-	0.5170	51.70%
CYP3A4 substrate	+	0.6501	65.01%
CYP2C9 substrate	+	0.5979	59.79%
CYP2D6 substrate	-	0.8144	81.44%
CYP3A4 inhibition	+	0.5551	55.51%
CYP2C9 inhibition	-	0.5449	54.49%
CYP2C19 inhibition	+	0.8970	89.70%
CYP2D6 inhibition	-	0.6468	64.68%
CYP1A2 inhibition	+	0.8242	82.42%
CYP2C8 inhibition	+	0.5416	54.16%
CYP inhibitory promiscuity	+	0.6694	66.94%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9413	94.13%
Carcinogenicity (trinary)	Non-required	0.6198	61.98%
Eye corrosion	-	0.9843	98.43%
Eye irritation	-	0.7401	74.01%
Skin irritation	-	0.8169	81.69%
Skin corrosion	-	0.9708	97.08%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4355	43.55%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	-	0.6091	60.91%
skin sensitisation	-	0.7789	77.89%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.7409	74.09%
Acute Oral Toxicity (c)	III	0.4498	44.98%
Estrogen receptor binding	+	0.9611	96.11%
Androgen receptor binding	+	0.8761	87.61%
Thyroid receptor binding	+	0.7042	70.42%
Glucocorticoid receptor binding	+	0.8762	87.62%
Aromatase binding	+	0.7164	71.64%
PPAR gamma	+	0.9257	92.57%
Honey bee toxicity	-	0.8686	86.86%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9559	95.59%

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	99.54%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.60%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.54%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.34%	98.95%
CHEMBL4208	P20618	Proteasome component C5	93.09%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.40%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.22%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.18%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.97%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.31%	93.99%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.99%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.72%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.74%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.16%	96.77%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.60%	95.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.40%	99.15%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.82%	91.07%
CHEMBL3820	P35557	Hexokinase type IV	83.58%	91.96%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.45%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.88%	99.17%
CHEMBL340	P08684	Cytochrome P450 3A4	82.72%	91.19%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.62%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.44%	95.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.11%	97.14%

Plants that contains it

• Ledebouria floribunda

Cross-Links

• PubChem: 163041140
• LOTUS: LTS0180915
• wikiData: Q105305196