(1R)-2,3-Dihydro-1-(formyloxy)-8bbeta-hydroxy-3beta-phenyl-3abeta-(3-hydroxy-4-methoxyphenyl)-6,8-dimethoxy-1H-cyclopenta[b]benzofuran-2alpha-carboxylic acid methyl ester

Details

• Internal ID: a33d2428-3508-4401-92f2-18c8e92b7ba7
• Taxonomy: Organoheterocyclic compounds > Benzofurans > Flavaglines
• IUPAC Name: methyl (1R,2R,3S,3aR,8bS)-1-formyloxy-8b-hydroxy-3a-(3-hydroxy-4-methoxyphenyl)-6,8-dimethoxy-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxylate
• SMILES (Canonical): COC1=C(C=C(C=C1)C23C(C(C(C2(C4=C(O3)C=C(C=C4OC)OC)O)OC=O)C(=O)OC)C5=CC=CC=C5)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)[C@]23[C@@H]([C@H]([C@H]([C@]2(C4=C(O3)C=C(C=C4OC)OC)O)OC=O)C(=O)OC)C5=CC=CC=C5)O
• InChI: InChI=1S/C29H28O10/c1-34-18-13-21(36-3)25-22(14-18)39-29(17-10-11-20(35-2)19(31)12-17)24(16-8-6-5-7-9-16)23(27(32)37-4)26(38-15-30)28(25,29)33/h5-15,23-24,26,31,33H,1-4H3/t23-,24-,26-,28+,29+/m1/s1
• InChI Key: XPXOKOTZMIKMIQ-IDAMAFBJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₂₈O₁₀
• Molecular Weight: 536.50 g/mol
• Exact Mass: 536.16824709 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.02
• H-Bond Acceptor: 10
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9777	97.77%
Caco-2	-	0.6007	60.07%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7889	78.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8761	87.61%
OATP1B3 inhibitior	-	0.2591	25.91%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9539	95.39%
P-glycoprotein inhibitior	+	0.8416	84.16%
P-glycoprotein substrate	-	0.6118	61.18%
CYP3A4 substrate	+	0.6562	65.62%
CYP2C9 substrate	-	0.6095	60.95%
CYP2D6 substrate	-	0.7603	76.03%
CYP3A4 inhibition	-	0.7104	71.04%
CYP2C9 inhibition	-	0.6344	63.44%
CYP2C19 inhibition	-	0.9277	92.77%
CYP2D6 inhibition	-	0.9337	93.37%
CYP1A2 inhibition	-	0.8991	89.91%
CYP2C8 inhibition	+	0.8343	83.43%
CYP inhibitory promiscuity	-	0.5796	57.96%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9443	94.43%
Carcinogenicity (trinary)	Danger	0.3592	35.92%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.8002	80.02%
Skin irritation	-	0.8028	80.28%
Skin corrosion	-	0.9596	95.96%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6033	60.33%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.9354	93.54%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.6457	64.57%
Acute Oral Toxicity (c)	III	0.4441	44.41%
Estrogen receptor binding	+	0.7583	75.83%
Androgen receptor binding	+	0.7877	78.77%
Thyroid receptor binding	+	0.6551	65.51%
Glucocorticoid receptor binding	+	0.7376	73.76%
Aromatase binding	-	0.5773	57.73%
PPAR gamma	+	0.6970	69.70%
Honey bee toxicity	-	0.7370	73.70%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9841	98.41%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.30%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.65%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.45%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.32%	86.33%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	93.24%	89.44%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.44%	95.50%
CHEMBL2535	P11166	Glucose transporter	90.43%	98.75%
CHEMBL240	Q12809	HERG	89.95%	89.76%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.50%	97.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.32%	99.15%
CHEMBL2581	P07339	Cathepsin D	89.05%	98.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	88.79%	91.07%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.23%	99.23%
CHEMBL1255126	O15151	Protein Mdm4	87.55%	90.20%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.92%	96.00%
CHEMBL340	P08684	Cytochrome P450 3A4	85.14%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.96%	92.62%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	84.31%	89.67%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.87%	99.17%
CHEMBL3492	P49721	Proteasome Macropain subunit	82.34%	90.24%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.31%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.05%	95.89%
CHEMBL4208	P20618	Proteasome component C5	80.68%	90.00%

Plants that contains it

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

Cross-Links

• PubChem: 10650033
• NPASS: NPC281034
• LOTUS: LTS0145306
• wikiData: Q105339053