4'-Hydroxy-3,6-dimethoxy-6'',6''-dimethylpyrano[2,3:7,8]flavone

Details

• Internal ID: b1e4dc1c-fbc7-4a41-b335-2d930a88aaea
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Pyranoflavonoids
• IUPAC Name: 2-(4-hydroxyphenyl)-3,6-dimethoxy-8,8-dimethylpyrano[2,3-h]chromen-4-one
• SMILES (Canonical): CC1(C=CC2=C3C(=CC(=C2O1)OC)C(=O)C(=C(O3)C4=CC=C(C=C4)O)OC)C
• SMILES (Isomeric): CC1(C=CC2=C3C(=CC(=C2O1)OC)C(=O)C(=C(O3)C4=CC=C(C=C4)O)OC)C
• InChI: InChI=1S/C22H20O6/c1-22(2)10-9-14-19-15(11-16(25-3)20(14)28-22)17(24)21(26-4)18(27-19)12-5-7-13(23)8-6-12/h5-11,23H,1-4H3
• InChI Key: LBQMBIWFYFFSFY-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₀O₆
• Molecular Weight: 380.40 g/mol
• Exact Mass: 380.12598835 g/mol
• Topological Polar Surface Area (TPSA): 74.20 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 4.37
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• DTXSID401124833
• LMPK12111587
• 3,6-Dimethoxy-8,8-dimethyl-2-(4-hydroxyphenyl)-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one
• 157072-30-5
• 4H,8H-Benzo[1,2-b:3,4-b']dipyran-4-one, 2-(4-hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9880	98.80%
Caco-2	+	0.5218	52.18%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7857	78.57%
OATP2B1 inhibitior	-	0.7201	72.01%
OATP1B1 inhibitior	+	0.9037	90.37%
OATP1B3 inhibitior	+	0.9764	97.64%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8583	85.83%
P-glycoprotein inhibitior	+	0.8352	83.52%
P-glycoprotein substrate	-	0.5304	53.04%
CYP3A4 substrate	+	0.6332	63.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7991	79.91%
CYP3A4 inhibition	+	0.8217	82.17%
CYP2C9 inhibition	-	0.7608	76.08%
CYP2C19 inhibition	+	0.8146	81.46%
CYP2D6 inhibition	-	0.8040	80.40%
CYP1A2 inhibition	-	0.6883	68.83%
CYP2C8 inhibition	+	0.8368	83.68%
CYP inhibitory promiscuity	+	0.6347	63.47%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Danger	0.5273	52.73%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.6845	68.45%
Skin irritation	-	0.7695	76.95%
Skin corrosion	-	0.9661	96.61%
Ames mutagenesis	+	0.5263	52.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.5476	54.76%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	-	0.5949	59.49%
skin sensitisation	-	0.8696	86.96%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	+	0.5641	56.41%
Acute Oral Toxicity (c)	III	0.5402	54.02%
Estrogen receptor binding	+	0.9027	90.27%
Androgen receptor binding	+	0.8355	83.55%
Thyroid receptor binding	+	0.7081	70.81%
Glucocorticoid receptor binding	+	0.8659	86.59%
Aromatase binding	+	0.6287	62.87%
PPAR gamma	+	0.8507	85.07%
Honey bee toxicity	-	0.7542	75.42%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9617	96.17%

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	99.29%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.55%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.63%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.21%	94.00%
CHEMBL242	Q92731	Estrogen receptor beta	92.44%	98.35%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.06%	86.33%
CHEMBL2581	P07339	Cathepsin D	90.66%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.13%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.33%	99.15%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.10%	85.14%
CHEMBL2535	P11166	Glucose transporter	89.02%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.41%	99.17%
CHEMBL1937	Q92769	Histone deacetylase 2	86.21%	94.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.20%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.02%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.44%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.67%	95.89%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.25%	95.78%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.23%	97.28%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.15%	95.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.10%	92.62%

Plants that contains it

• Agnorhiza bolanderi
• Anaxagorea crassipetala
• Araujia sericifera
• Arnica nevadensis
• Artemisia gmelinii
• Beyeria sulcata var. brevipes
• Bursaria spinosa
• Chloranthus tianmushanensis
• Chromolaena odorata
• Chromolaena pulchella
• Citrus × aurantium
• Craibia grandiflora
• Dendrosenecio kilimanjari
• Dipterocarpus alatus
• Drosera peltata
• Echinops amplexicaulis
• Ficus formosana
• Gardenia fosbergii
• Ilex affinis
• Isodon umbrosus
• Kaempferia pulchra
• Litogyne gariepina
• Odixia angusta
• Prosopis glandulosa
• Prunus laurocerasus
• Pteris plumieri
• Quercus cerris
• Salvia officinalis
• Senecio squalidus
• Seriphidium cinum
• Sesbania punicea
• Simira eliezeriana
• Sorbus pallescens
• Stenostomum lucidum
• Taxodium huegelii
• Vitex madiensis

Cross-Links

• PubChem: 44258693
• NPASS: NPC220615
• LOTUS: LTS0075526
• wikiData: Q105149574