(2Z)-6-hydroxy-2-((4-hydroxy-3-methoxyphenyl)methylidene)-1-benzofuran-3-one

Details

• Internal ID: a7c1e09a-f353-4534-89cf-157b787a7104
• Taxonomy: Phenylpropanoids and polyketides > Aurone flavonoids
• IUPAC Name: (2Z)-6-hydroxy-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-1-benzofuran-3-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C=C2C(=O)C3=C(O2)C=C(C=C3)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C\2/C(=O)C3=C(O2)C=C(C=C3)O)O
• InChI: InChI=1S/C16H12O5/c1-20-14-6-9(2-5-12(14)18)7-15-16(19)11-4-3-10(17)8-13(11)21-15/h2-8,17-18H,1H3/b15-7-
• InChI Key: HPSPCMSCDNHZJM-CHHVJCJISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₂O₅
• Molecular Weight: 284.26 g/mol
• Exact Mass: 284.06847348 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 2.90

Synonyms

• (2Z)-6-hydroxy-2-((4-hydroxy-3-methoxyphenyl)methylidene)-1-benzofuran-3-one
• RefChem:69040
• Sid26657808
• 32396-80-8
• MLS000863596
• 4',6-Dihydroxy-3'-methoxyaurone
• SMR000440745
• 942986-93-8
• CHEMBL446827
• MEGxp0_001777
• orb1991682
• SCHEMBL31238393
• ACon0_000986
• ACon1_000021
• BDBM69395
• cid_16376440
• DTXSID201345728
• HMS2269L17
• AKOS002557776
• NCGC00168869-01
• (2Z)-6-hydroxy-2-vanillylidene-coumaran-3-one
• BRD-K01291894-001-01-6
• (2Z)-6-hydroxy-2-[(4-hydroxy-3-methoxyphenyl)methylidene]-3-benzofuranone
• (Z)-6-Hydroxy-2-(4-hydroxy-3-methoxybenzylidene)benzofuran-3(2H)-one
• (2Z)-2-[(3-methoxy-4-oxidanyl-phenyl)methylidene]-6-oxidanyl-1-benzofuran-3-one
• (2Z)-6-Hydroxy-2-[(4-hydroxy-3-methoxyphenyl)methylene]-3(2H)-benzofuranone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	28183.8 nM	Potency	PMID: 18077425
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	25118.9 nM	Potency	PMID: 22136907
CHEMBL1293224	P10636	Microtubule-associated protein tau	2511.9 nM	Potency	PMID: 12088423
CHEMBL1293277	O15118	Niemann-Pick C1 protein	3162.3 nM	Potency	DOI: 10.6019/CHEMBL1201861
CHEMBL1293294	P51151	Ras-related protein Rab-9A	3981.1 nM	Potency	PMID: 17253864
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	11220.2 nM	Potency	PMID: 16989518

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.48%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.69%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.13%	95.56%
CHEMBL3194	P02766	Transthyretin	93.58%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.55%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.89%	86.33%
CHEMBL2581	P07339	Cathepsin D	92.16%	98.95%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	86.16%	80.78%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.11%	99.23%
CHEMBL2535	P11166	Glucose transporter	85.71%	98.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.95%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.94%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.17%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	83.89%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.74%	96.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.49%	94.00%
CHEMBL4208	P20618	Proteasome component C5	81.91%	90.00%

Plants that contains it

• Dipteryx odorata
• Schumanniophyton magnificum

Cross-Links

• PubChem: 16376440
• NPASS: NPC304954
• ChEMBL: CHEMBL446827
• LOTUS: LTS0208474
• wikiData: Q105033232