(1R,3S,3aR,8bS)-3a-(3,4-dimethoxyphenyl)-6,8-dimethoxy-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-1,8b-diol

Details

• Internal ID: 16211989-0e12-4559-b79b-fc6e2a7bffa5
• Taxonomy: Organoheterocyclic compounds > Benzofurans > Flavaglines
• IUPAC Name: (1R,3S,3aR,8bS)-3a-(3,4-dimethoxyphenyl)-6,8-dimethoxy-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-1,8b-diol
• SMILES (Canonical): COC1=C(C=C(C=C1)C23C(CC(C2(C4=C(O3)C=C(C=C4OC)OC)O)O)C5=CC=CC=C5)OC
• SMILES (Isomeric): COC1=C(C=C(C=C1)[C@]23[C@@H](C[C@H]([C@]2(C4=C(O3)C=C(C=C4OC)OC)O)O)C5=CC=CC=C5)OC
• InChI: InChI=1S/C27H28O7/c1-30-18-13-22(33-4)25-23(14-18)34-27(17-10-11-20(31-2)21(12-17)32-3)19(15-24(28)26(25,27)29)16-8-6-5-7-9-16/h5-14,19,24,28-29H,15H2,1-4H3/t19-,24+,26+,27-/m0/s1
• InChI Key: LVGAHKPUZPMMOH-HCSVXLCASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₈O₇
• Molecular Weight: 464.50 g/mol
• Exact Mass: 464.18350323 g/mol
• Topological Polar Surface Area (TPSA): 86.60 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.74
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9724	97.24%
Caco-2	+	0.5434	54.34%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6618	66.18%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8988	89.88%
OATP1B3 inhibitior	+	0.9499	94.99%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9082	90.82%
P-glycoprotein inhibitior	+	0.8046	80.46%
P-glycoprotein substrate	-	0.5512	55.12%
CYP3A4 substrate	+	0.6218	62.18%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	+	0.4780	47.80%
CYP3A4 inhibition	-	0.7471	74.71%
CYP2C9 inhibition	-	0.8198	81.98%
CYP2C19 inhibition	-	0.6508	65.08%
CYP2D6 inhibition	-	0.8483	84.83%
CYP1A2 inhibition	-	0.7076	70.76%
CYP2C8 inhibition	+	0.7067	70.67%
CYP inhibitory promiscuity	-	0.6230	62.30%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.3572	35.72%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.8352	83.52%
Skin irritation	-	0.7762	77.62%
Skin corrosion	-	0.9283	92.83%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3815	38.15%
Micronuclear	+	0.6559	65.59%
Hepatotoxicity	-	0.6039	60.39%
skin sensitisation	-	0.8775	87.75%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.5685	56.85%
Acute Oral Toxicity (c)	III	0.4677	46.77%
Estrogen receptor binding	+	0.7928	79.28%
Androgen receptor binding	+	0.7930	79.30%
Thyroid receptor binding	+	0.7460	74.60%
Glucocorticoid receptor binding	+	0.7472	74.72%
Aromatase binding	+	0.5686	56.86%
PPAR gamma	+	0.6721	67.21%
Honey bee toxicity	-	0.8440	84.40%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6251	62.51%
Fish aquatic toxicity	+	0.8823	88.23%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.15%	96.09%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	96.07%	89.44%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.22%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.64%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.63%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.07%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.29%	97.14%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.42%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.40%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.31%	95.50%
CHEMBL4208	P20618	Proteasome component C5	85.15%	90.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.62%	94.08%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	84.36%	94.03%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.28%	92.94%
CHEMBL221	P23219	Cyclooxygenase-1	83.40%	90.17%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.30%	93.99%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.91%	96.00%
CHEMBL2581	P07339	Cathepsin D	82.79%	98.95%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.87%	96.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.72%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.10%	92.62%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	80.98%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.95%	91.07%

Plants that contains it

• Aglaia odorata

Cross-Links

• PubChem: 100978907
• LOTUS: LTS0124570
• wikiData: Q105157839