methyl 3a-(1,3-benzodioxol-5-yl)-1-formyloxy-8b-hydroxy-6,8-dimethoxy-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxylate

Details

• Internal ID: 33d5a4d3-8477-4b76-837e-7f2c243d8b72
• Taxonomy: Organoheterocyclic compounds > Benzofurans > Flavaglines
• IUPAC Name: methyl 3a-(1,3-benzodioxol-5-yl)-1-formyloxy-8b-hydroxy-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)OC=O)O
• SMILES (Isomeric): 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)OC=O)O
• InChI: InChI=1S/C29H26O10/c1-33-18-12-21(34-2)25-22(13-18)39-29(17-9-10-19-20(11-17)38-15-37-19)24(16-7-5-4-6-8-16)23(27(31)35-3)26(36-14-30)28(25,29)32/h4-14,23-24,26,32H,15H2,1-3H3
• InChI Key: XKYRDXZNJADCQR-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₂₆O₁₀
• Molecular Weight: 534.50 g/mol
• Exact Mass: 534.15259702 g/mol
• Topological Polar Surface Area (TPSA): 119.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.04
• H-Bond Acceptor: 10
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9820	98.20%
Caco-2	-	0.5982	59.82%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7923	79.23%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8778	87.78%
OATP1B3 inhibitior	+	0.9053	90.53%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9776	97.76%
P-glycoprotein inhibitior	+	0.8923	89.23%
P-glycoprotein substrate	-	0.6403	64.03%
CYP3A4 substrate	+	0.6549	65.49%
CYP2C9 substrate	-	0.6085	60.85%
CYP2D6 substrate	-	0.8110	81.10%
CYP3A4 inhibition	+	0.8074	80.74%
CYP2C9 inhibition	+	0.7835	78.35%
CYP2C19 inhibition	-	0.6162	61.62%
CYP2D6 inhibition	-	0.8608	86.08%
CYP1A2 inhibition	-	0.9289	92.89%
CYP2C8 inhibition	+	0.7182	71.82%
CYP inhibitory promiscuity	+	0.5490	54.90%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9343	93.43%
Carcinogenicity (trinary)	Non-required	0.3828	38.28%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.8698	86.98%
Skin irritation	-	0.8106	81.06%
Skin corrosion	-	0.9580	95.80%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	+	0.7974	79.74%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.8204	82.04%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	+	0.6774	67.74%
Acute Oral Toxicity (c)	III	0.5253	52.53%
Estrogen receptor binding	+	0.8121	81.21%
Androgen receptor binding	+	0.7978	79.78%
Thyroid receptor binding	+	0.6616	66.16%
Glucocorticoid receptor binding	+	0.8095	80.95%
Aromatase binding	+	0.5223	52.23%
PPAR gamma	+	0.7054	70.54%
Honey bee toxicity	-	0.7553	75.53%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9734	97.34%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL240	Q12809	HERG	99.38%	89.76%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.82%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.80%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.68%	96.09%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	95.97%	89.44%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.23%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.63%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	93.44%	92.62%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.74%	95.50%
CHEMBL2535	P11166	Glucose transporter	91.35%	98.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	91.14%	97.14%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.61%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.01%	96.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.68%	94.80%
CHEMBL3492	P49721	Proteasome Macropain subunit	88.77%	90.24%
CHEMBL4208	P20618	Proteasome component C5	88.29%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.83%	99.23%
CHEMBL2581	P07339	Cathepsin D	87.77%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	85.95%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.63%	95.89%
CHEMBL5028	O14672	ADAM10	83.92%	97.50%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	83.51%	85.49%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.29%	96.77%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.72%	91.07%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.53%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.36%	97.09%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	81.85%	89.67%
CHEMBL221	P23219	Cyclooxygenase-1	80.48%	90.17%

Plants that contains it

• Aglaia elliptica

Cross-Links

• PubChem: 85056561
• LOTUS: LTS0251424
• wikiData: Q105329781