8-[4-(4-Oxo-5,7-dihydroxy-4H-1-benzopyran-2-yl)phenoxy]-5,7,4'-trihydroxyflavone

Details

• Internal ID: 9c6f2d0b-33f8-4bf8-9242-7a9963239b29
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones
• IUPAC Name: 8-[4-(5,7-dihydroxy-4-oxochromen-2-yl)phenoxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)OC4=CC=C(C=C4)C5=CC(=O)C6=C(C=C(C=C6O5)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)OC4=CC=C(C=C4)C5=CC(=O)C6=C(C=C(C=C6O5)O)O)O
• InChI: InChI=1S/C30H18O10/c31-16-5-1-14(2-6-16)25-13-22(36)28-20(34)11-23(37)29(30(28)40-25)38-18-7-3-15(4-8-18)24-12-21(35)27-19(33)9-17(32)10-26(27)39-24/h1-13,31-34,37H
• InChI Key: DLWAHHFLQNUOIA-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₁₈O₁₀
• Molecular Weight: 538.50 g/mol
• Exact Mass: 538.08999677 g/mol
• Topological Polar Surface Area (TPSA): 163.00 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 5.55
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• CHEMBL2172395
• 8-[4-(4-Oxo-5,7-dihydroxy-4H-1-benzopyran-2-yl)phenoxy]-5,7,4'-trihydroxyflavone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8926	89.26%
Caco-2	-	0.8754	87.54%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6583	65.83%
OATP2B1 inhibitior	+	0.5763	57.63%
OATP1B1 inhibitior	+	0.8403	84.03%
OATP1B3 inhibitior	+	0.8553	85.53%
MATE1 inhibitior	+	0.6800	68.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7644	76.44%
P-glycoprotein inhibitior	+	0.7249	72.49%
P-glycoprotein substrate	-	0.8459	84.59%
CYP3A4 substrate	+	0.5939	59.39%
CYP2C9 substrate	-	0.6218	62.18%
CYP2D6 substrate	-	0.8508	85.08%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	+	0.8318	83.18%
CYP2C19 inhibition	+	0.6307	63.07%
CYP2D6 inhibition	-	0.9004	90.04%
CYP1A2 inhibition	+	0.6264	62.64%
CYP2C8 inhibition	+	0.8718	87.18%
CYP inhibitory promiscuity	+	0.5994	59.94%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6849	68.49%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.7597	75.97%
Skin irritation	-	0.5751	57.51%
Skin corrosion	-	0.9492	94.92%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6197	61.97%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.8792	87.92%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	II	0.4709	47.09%
Estrogen receptor binding	+	0.8193	81.93%
Androgen receptor binding	+	0.9442	94.42%
Thyroid receptor binding	+	0.6444	64.44%
Glucocorticoid receptor binding	+	0.8391	83.91%
Aromatase binding	+	0.5817	58.17%
PPAR gamma	+	0.8104	81.04%
Honey bee toxicity	-	0.6951	69.51%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5650	56.50%
Fish aquatic toxicity	+	0.9181	91.81%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1860	P10827	Thyroid hormone receptor alpha	98.38%	99.15%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.35%	91.11%
CHEMBL242	Q92731	Estrogen receptor beta	98.18%	98.35%
CHEMBL3194	P02766	Transthyretin	97.54%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.77%	94.00%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	92.59%	83.57%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.93%	89.00%
CHEMBL1929	P47989	Xanthine dehydrogenase	89.29%	96.12%
CHEMBL2581	P07339	Cathepsin D	89.06%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.96%	95.56%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	88.50%	95.78%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	86.06%	89.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.64%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.79%	86.33%
CHEMBL4208	P20618	Proteasome component C5	84.56%	90.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.13%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.78%	99.17%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.70%	91.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.23%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	83.01%	94.73%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	82.39%	93.65%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.82%	99.23%

Plants that contains it

• Breonia chinensis
• Campylotropis hirtella
• Ceropegia dichotoma
• Crinum moorei
• Crotalaria candicans
• Dendrobium loddigesii
• Distephanus angulifolius
• Eucalyptus apodophylla
• Garcinia vilersiana
• Glycosmis macrophylla
• Gypsophila perfoliata
• Hypericum polyanthemum
• Juniperus drupacea
• Lanaria lanata
• Lophostemon confertus
• Mentha × gentilis
• Ononis spinosa
• Orbivestus karaguensis
• Ouratea semiserrata
• Pentaclethra macrophylla
• Periploca sepium
• Pinalia japonica
• Plectranthus hereroensis
• Prunus dulcis
• Pterocaulon virgatum
• Rhodiola semenovii
• Salvia sessei
• Sonneratia caseolaris
• Stephania zippeliana
• Veronica polita

Cross-Links

• PubChem: 11272651
• NPASS: NPC34089
• ChEMBL: CHEMBL2172395
• LOTUS: LTS0209318
• wikiData: Q104938899