8bH-Cyclopenta[b]benzofuran-1,8b-diol, 3a-(1,3-benzodioxol-5-yl)-1,2,3,3a-tetrahydro-6,8-dimethoxy-3-phenyl-, (1R,3S,3aR,8bS)-

Details

• Internal ID: 7ba5f3c3-ff00-4730-b347-e8569d48eddb
• Taxonomy: Organoheterocyclic compounds > Benzofurans > Flavaglines
• IUPAC Name: (1R,3S,3aR,8bS)-3a-(1,3-benzodioxol-5-yl)-6,8-dimethoxy-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-1,8b-diol
• SMILES (Canonical): COC1=CC2=C(C(=C1)OC)C3(C(CC(C3(O2)C4=CC5=C(C=C4)OCO5)C6=CC=CC=C6)O)O
• SMILES (Isomeric): COC1=CC2=C(C(=C1)OC)[C@@]3([C@@H](C[C@H]([C@@]3(O2)C4=CC5=C(C=C4)OCO5)C6=CC=CC=C6)O)O
• InChI: InChI=1S/C26H24O7/c1-29-17-11-21(30-2)24-22(12-17)33-26(16-8-9-19-20(10-16)32-14-31-19)18(13-23(27)25(24,26)28)15-6-4-3-5-7-15/h3-12,18,23,27-28H,13-14H2,1-2H3/t18-,23+,25+,26-/m0/s1
• InChI Key: ZPHNJERYFDKEMS-LHVBDCGNSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₄O₇
• Molecular Weight: 448.50 g/mol
• Exact Mass: 448.15220310 g/mol
• Topological Polar Surface Area (TPSA): 86.60 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.46
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• 201212-33-1
• CHEMBL2332223
• (1R)-2,3-Dihydro-3beta-phenyl-3abeta-(1,3-benzodioxole-5-yl)-6,8-dimethoxy-1H-cyclopenta[b]benzofuran-1,8bbeta-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9369	93.69%
Caco-2	-	0.5742	57.42%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6982	69.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8837	88.37%
OATP1B3 inhibitior	+	0.9389	93.89%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9077	90.77%
P-glycoprotein inhibitior	+	0.8394	83.94%
P-glycoprotein substrate	-	0.6516	65.16%
CYP3A4 substrate	+	0.6215	62.15%
CYP2C9 substrate	-	0.8027	80.27%
CYP2D6 substrate	+	0.3622	36.22%
CYP3A4 inhibition	+	0.5413	54.13%
CYP2C9 inhibition	-	0.6566	65.66%
CYP2C19 inhibition	-	0.6150	61.50%
CYP2D6 inhibition	-	0.7505	75.05%
CYP1A2 inhibition	-	0.8279	82.79%
CYP2C8 inhibition	+	0.5910	59.10%
CYP inhibitory promiscuity	-	0.6245	62.45%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.3963	39.63%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.8902	89.02%
Skin irritation	-	0.7896	78.96%
Skin corrosion	-	0.9363	93.63%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3922	39.22%
Micronuclear	+	0.7759	77.59%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8459	84.59%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.4557	45.57%
Acute Oral Toxicity (c)	III	0.6487	64.87%
Estrogen receptor binding	+	0.8120	81.20%
Androgen receptor binding	+	0.8085	80.85%
Thyroid receptor binding	+	0.7463	74.63%
Glucocorticoid receptor binding	+	0.7448	74.48%
Aromatase binding	+	0.5943	59.43%
PPAR gamma	+	0.6832	68.32%
Honey bee toxicity	-	0.8069	80.69%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6051	60.51%
Fish aquatic toxicity	+	0.8875	88.75%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5533	Q04206	Nuclear factor NF-kappa-B p65 subunit	0.33 nM	ED50	PMID: 23301897

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.24%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.62%	96.09%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	96.06%	89.44%
CHEMBL240	Q12809	HERG	95.14%	89.76%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.46%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.82%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.61%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.81%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.38%	92.62%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.25%	96.77%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.69%	97.14%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	87.33%	94.08%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.04%	95.50%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	86.44%	94.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.09%	95.89%
CHEMBL4208	P20618	Proteasome component C5	85.79%	90.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.14%	96.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	84.38%	94.80%
CHEMBL2581	P07339	Cathepsin D	84.28%	98.95%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	83.66%	94.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.80%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.31%	89.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.25%	96.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.17%	94.00%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	80.07%	100.00%

Plants that contains it

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

Cross-Links

• PubChem: 10623340
• NPASS: NPC189730
• ChEMBL: CHEMBL2332223
• LOTUS: LTS0040377
• wikiData: Q105380902