5-Hydroxyauranetin

Details

• Internal ID: d738895d-b313-4096-a441-a09d8b77d272
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 8-O-methylated flavonoids
• IUPAC Name: 5-hydroxy-3,6,7,8-tetramethoxy-2-(4-methoxyphenyl)chromen-4-one
• SMILES (Canonical): COC1=CC=C(C=C1)C2=C(C(=O)C3=C(C(=C(C(=C3O2)OC)OC)OC)O)OC
• SMILES (Isomeric): COC1=CC=C(C=C1)C2=C(C(=O)C3=C(C(=C(C(=C3O2)OC)OC)OC)O)OC
• InChI: InChI=1S/C20H20O8/c1-23-11-8-6-10(7-9-11)15-17(24-2)13(21)12-14(22)18(25-3)20(27-5)19(26-4)16(12)28-15/h6-9,22H,1-5H3
• InChI Key: KBYYZSYVUWCARH-UHFFFAOYSA-N
• Popularity: 15 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₈
• Molecular Weight: 388.40 g/mol
• Exact Mass: 388.11581759 g/mol
• Topological Polar Surface Area (TPSA): 92.70 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.21
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• 5-Hydroxy-3,6,7,8,4'-pentamethoxyflavone
• 5-hydroxy-3,6,7,8-tetramethoxy-2-(4-methoxyphenyl)chromen-4-one
• 50439-46-8
• 5-Hydroxy-3,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-4H-1-Benzopyran-4-one
• 4'-O-Methylcalycopterin
• CHEMBL504047
• MEGxp0_001194
• SCHEMBL4066374
• CHEBI:175931
• DTXSID501150275
• LMPK12113314
• 5-Hydroxy-3,4',6,7,8-pentamethoxyflavone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9823	98.23%
Caco-2	+	0.7802	78.02%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7745	77.45%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9239	92.39%
OATP1B3 inhibitior	+	0.9817	98.17%
MATE1 inhibitior	+	0.5400	54.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.5853	58.53%
P-glycoprotein inhibitior	+	0.9041	90.41%
P-glycoprotein substrate	-	0.9128	91.28%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.6401	64.01%
CYP2D6 substrate	-	0.8296	82.96%
CYP3A4 inhibition	-	0.5748	57.48%
CYP2C9 inhibition	-	0.8861	88.61%
CYP2C19 inhibition	+	0.5778	57.78%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.8530	85.30%
CYP2C8 inhibition	+	0.5491	54.91%
CYP inhibitory promiscuity	+	0.6103	61.03%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5716	57.16%
Eye corrosion	-	0.9793	97.93%
Eye irritation	-	0.5798	57.98%
Skin irritation	-	0.7150	71.50%
Skin corrosion	-	0.9836	98.36%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3790	37.90%
Micronuclear	+	0.8359	83.59%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.9504	95.04%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.5702	57.02%
Acute Oral Toxicity (c)	II	0.4982	49.82%
Estrogen receptor binding	+	0.8510	85.10%
Androgen receptor binding	+	0.7980	79.80%
Thyroid receptor binding	+	0.7328	73.28%
Glucocorticoid receptor binding	+	0.8033	80.33%
Aromatase binding	+	0.6730	67.30%
PPAR gamma	+	0.7881	78.81%
Honey bee toxicity	-	0.9314	93.14%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.8902	89.02%

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	98.46%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.05%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.27%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.56%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.77%	99.15%
CHEMBL2581	P07339	Cathepsin D	89.13%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.45%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.03%	89.00%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	85.48%	81.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.30%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	84.18%	94.73%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	84.06%	87.67%
CHEMBL4208	P20618	Proteasome component C5	82.00%	90.00%
CHEMBL1907	P15144	Aminopeptidase N	81.01%	93.31%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	80.30%	85.30%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	80.17%	94.42%

Plants that contains it

• Bellardia trixago
• Craibiodendron henryi
• Crataegus tanacetifolia
• Croton cascarilloides
• Dicranopteris linearis
• Drummondita calida
• Gamochaeta malvinensis
• Herissantia tiubae
• Monechma ciliatum
• Nothofagus alpina
• Pseudognaphalium affine
• Salacia elliptica
• Stachys aegyptiaca

Cross-Links

• PubChem: 11079623
• NPASS: NPC143828
• ChEMBL: CHEMBL504047
• LOTUS: LTS0215144
• wikiData: Q104400009