Aureusidin

Details

• Internal ID: e37cd482-38b2-431c-9be1-50f696b59fab
• Taxonomy: Phenylpropanoids and polyketides > Aurone flavonoids
• IUPAC Name: (2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-4,6-dihydroxy-1-benzofuran-3-one
• SMILES (Canonical): C1=CC(=C(C=C1C=C2C(=O)C3=C(C=C(C=C3O2)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1/C=C\2/C(=O)C3=C(C=C(C=C3O2)O)O)O)O
• InChI: InChI=1S/C15H10O6/c16-8-5-11(19)14-12(6-8)21-13(15(14)20)4-7-1-2-9(17)10(18)3-7/h1-6,16-19H/b13-4-
• InChI Key: WBEFUVAYFSOUEA-PQMHYQBVSA-N
• Popularity: 13 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₀O₆
• Molecular Weight: 286.24 g/mol
• Exact Mass: 286.04773803 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.13
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

• 38216-54-5
• Cernuin
• AUREUSIDIN(RG)
• (2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-4,6-dihydroxy-1-benzofuran-3-one
• U8B4XHN2DX
• CHEBI:18149
• 480-70-6
• (2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-4,6-dihydroxy-1-benzofuran-3(2H)-one
• Auresudidin
• Auresidin
• UNII-U8B4XHN2DX
• CHEMBL593229
• SCHEMBL4408442
• 4,6,3',4'-Tetrahydroxyaurone
• WBEFUVAYFSOUEA-PQMHYQBVSA-N
• DTXSID201028835
• EX-A6751
• BDBM50439491
• (2Z)-2-[(3,4-dihydroxyphenyl)methylene]-4,6-dihydroxy-3(2H)-benzofuranone
• AKOS040762813
• AKOS040763842
• MS-24074
• (Z)-4,6,3',4'-TETRAHYDROXYAURONE
• C08576
• Q4822317
• (2Z)-2-[(3,4-dihydroxyphenyl)methylene]-4,6-dihydroxy-benzofuran-3-one
• (2Z)-2-((3,4-DIHYDROXYPHENYL)METHYLENE)-4,6-DIHYDROXY-3(2H)-BENZOFURANONE (ACI)
• (2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-4,6-dihydroxy-2,3-dihydro-1-benzofuran-3-one
• 3(2H)-BENZOFURANONE, 2-((3,4-DIHYDROXYPHENYL)METHYLENE)-4,6-DIHYDROXY-, (Z)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9831	98.31%
Caco-2	-	0.5245	52.45%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5189	51.89%
OATP2B1 inhibitior	+	0.5586	55.86%
OATP1B1 inhibitior	+	0.9443	94.43%
OATP1B3 inhibitior	+	0.9626	96.26%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8103	81.03%
P-glycoprotein inhibitior	-	0.9139	91.39%
P-glycoprotein substrate	-	0.9801	98.01%
CYP3A4 substrate	-	0.5921	59.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8409	84.09%
CYP3A4 inhibition	+	0.5482	54.82%
CYP2C9 inhibition	-	0.6091	60.91%
CYP2C19 inhibition	-	0.7345	73.45%
CYP2D6 inhibition	-	0.8858	88.58%
CYP1A2 inhibition	+	0.9402	94.02%
CYP2C8 inhibition	-	0.6368	63.68%
CYP inhibitory promiscuity	+	0.8920	89.20%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4353	43.53%
Eye corrosion	-	0.9859	98.59%
Eye irritation	+	0.9824	98.24%
Skin irritation	+	0.5420	54.20%
Skin corrosion	-	0.9301	93.01%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8899	88.99%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.5290	52.90%
skin sensitisation	+	0.5529	55.29%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.5670	56.70%
Acute Oral Toxicity (c)	IV	0.3730	37.30%
Estrogen receptor binding	+	0.8187	81.87%
Androgen receptor binding	+	0.8734	87.34%
Thyroid receptor binding	+	0.6641	66.41%
Glucocorticoid receptor binding	+	0.7864	78.64%
Aromatase binding	+	0.8012	80.12%
PPAR gamma	+	0.7575	75.75%
Honey bee toxicity	-	0.7607	76.07%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9874	98.74%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL325	Q13547	Histone deacetylase 1	38000 nM	IC50	PMID: 25455492
CHEMBL1937	Q92769	Histone deacetylase 2	38900 nM	IC50	PMID: 25455492
CHEMBL1865	Q9UBN7	Histone deacetylase 6	48500 nM	IC50	PMID: 25455492

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.45%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.09%	91.11%
CHEMBL1929	P47989	Xanthine dehydrogenase	97.41%	96.12%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.83%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.51%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.95%	94.45%
CHEMBL3194	P02766	Transthyretin	92.91%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.50%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	89.69%	94.73%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	89.64%	93.40%
CHEMBL2581	P07339	Cathepsin D	86.87%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.99%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.83%	99.15%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.13%	90.71%
CHEMBL4208	P20618	Proteasome component C5	81.16%	90.00%

Plants that contains it

• Antirrhinum majus
• Citrus limon
• Cyperus capitatus
• Cyperus iria
• Ipomoea nil
• Zinnia elegans

Cross-Links

• PubChem: 5281220
• NPASS: NPC19545
• ChEMBL: CHEMBL593229
• LOTUS: LTS0260686
• wikiData: Q4822317