(1R)-1alpha,8bbeta-Dihydroxy-3beta-phenyl-3abeta-(1,3-benzodioxol-5-yl)-6,8-dimethoxy-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2alpha-carboxylic acid methyl ester

Details

• Internal ID: 595662df-4b4c-43f4-bde3-7a9a90338d74
• Taxonomy: Organoheterocyclic compounds > Benzofurans > Flavaglines
• IUPAC Name: methyl (1R,2R,3S,3aR,8bS)-3a-(1,3-benzodioxol-5-yl)-1,8b-dihydroxy-6,8-dimethoxy-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxylate
• SMILES (Canonical): COC1=CC2=C(C(=C1)OC)C3(C(C(C(C3(O2)C4=CC5=C(C=C4)OCO5)C6=CC=CC=C6)C(=O)OC)O)O
• SMILES (Isomeric): COC1=CC2=C(C(=C1)OC)[C@@]3([C@@H]([C@@H]([C@H]([C@@]3(O2)C4=CC5=C(C=C4)OCO5)C6=CC=CC=C6)C(=O)OC)O)O
• InChI: InChI=1S/C28H26O9/c1-32-17-12-20(33-2)24-21(13-17)37-28(16-9-10-18-19(11-16)36-14-35-18)23(15-7-5-4-6-8-15)22(26(30)34-3)25(29)27(24,28)31/h4-13,22-23,25,29,31H,14H2,1-3H3/t22-,23-,25-,27+,28+/m1/s1
• InChI Key: SAGBWAVFZFVBBQ-GWNOIRNCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₆O₉
• Molecular Weight: 506.50 g/mol
• Exact Mass: 506.15768240 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 3.10

Synonyms

• CHEMBL1986494
• CCG-205925
• NSC-687939
• NCI60_031735
• (1R)-1alpha,8bbeta-Dihydroxy-3beta-phenyl-3abeta-(1,3-benzodioxol-5-yl)-6,8-dimethoxy-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2alpha-carboxylic acid methyl ester

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
CHEMBL5533	Q04206	Nuclear factor NF-kappa-B p65 subunit	3.54 nM	ED50	PMID: 23301897

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL240	Q12809	HERG	98.69%	89.76%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.60%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.52%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.20%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.85%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.40%	85.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.63%	92.62%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	91.85%	89.44%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.83%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	90.47%	97.14%
CHEMBL2581	P07339	Cathepsin D	89.10%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	88.65%	91.19%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.91%	96.00%
CHEMBL4208	P20618	Proteasome component C5	87.80%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.76%	99.23%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.49%	95.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.96%	96.77%
CHEMBL2535	P11166	Glucose transporter	85.80%	98.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.29%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.90%	95.89%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.76%	94.80%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.50%	89.00%
CHEMBL5028	O14672	ADAM10	82.00%	97.50%

Plants that contains it

• Aglaia elliptica
• Aglaia perviridis
• Aglaia spectabilis
• Ammodendron karelinii
• Citrus japonica
• Duguetia chrysocarpa
• Phaseolus coccineus
• Pinus yunnanensis
• Pyrola media
• Senecio rosmarinifolius
• Sicyos edulis

Cross-Links

• PubChem: 390507
• NPASS: NPC23593
• ChEMBL: CHEMBL1986494
• LOTUS: LTS0018334
• wikiData: Q105248828