1,8b-dihydroxy-3a-(3-hydroxy-4-methoxyphenyl)-6,8-dimethoxy-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide

Details

• Internal ID: 40c9fa7a-25e4-4463-a526-f71f288ac48a
• Taxonomy: Organoheterocyclic compounds > Benzofurans > Flavaglines
• IUPAC Name: 1,8b-dihydroxy-3a-(3-hydroxy-4-methoxyphenyl)-6,8-dimethoxy-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide
• SMILES (Canonical): COC1=C(C=C(C=C1)C23C(C(C(C2(C4=C(O3)C=C(C=C4OC)OC)O)O)C(=O)N)C5=CC=CC=C5)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)C23C(C(C(C2(C4=C(O3)C=C(C=C4OC)OC)O)O)C(=O)N)C5=CC=CC=C5)O
• InChI: InChI=1S/C27H27NO8/c1-33-16-12-19(35-3)23-20(13-16)36-27(15-9-10-18(34-2)17(29)11-15)22(14-7-5-4-6-8-14)21(25(28)31)24(30)26(23,27)32/h4-13,21-22,24,29-30,32H,1-3H3,(H2,28,31)
• InChI Key: YRDYBAJOZQAAHP-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₇NO₈
• Molecular Weight: 493.50 g/mol
• Exact Mass: 493.17366682 g/mol
• Topological Polar Surface Area (TPSA): 141.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.15
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9495	94.95%
Caco-2	-	0.6601	66.01%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5096	50.96%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9007	90.07%
OATP1B3 inhibitior	+	0.9419	94.19%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.9021	90.21%
P-glycoprotein inhibitior	+	0.7435	74.35%
P-glycoprotein substrate	-	0.6629	66.29%
CYP3A4 substrate	+	0.6432	64.32%
CYP2C9 substrate	-	0.6077	60.77%
CYP2D6 substrate	-	0.7629	76.29%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.8062	80.62%
CYP2C19 inhibition	-	0.7764	77.64%
CYP2D6 inhibition	-	0.8630	86.30%
CYP1A2 inhibition	-	0.7800	78.00%
CYP2C8 inhibition	+	0.7920	79.20%
CYP inhibitory promiscuity	-	0.5636	56.36%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.4347	43.47%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.8261	82.61%
Skin irritation	-	0.8310	83.10%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5684	56.84%
Micronuclear	+	0.7500	75.00%
Hepatotoxicity	-	0.5414	54.14%
skin sensitisation	-	0.8916	89.16%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.5759	57.59%
Acute Oral Toxicity (c)	III	0.5870	58.70%
Estrogen receptor binding	+	0.7810	78.10%
Androgen receptor binding	+	0.7851	78.51%
Thyroid receptor binding	+	0.6464	64.64%
Glucocorticoid receptor binding	+	0.6763	67.63%
Aromatase binding	-	0.5601	56.01%
PPAR gamma	+	0.7088	70.88%
Honey bee toxicity	-	0.8016	80.16%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5349	53.49%
Fish aquatic toxicity	+	0.7716	77.16%

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	98.44%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.42%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.64%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.94%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.09%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.47%	94.45%
CHEMBL2581	P07339	Cathepsin D	87.87%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.42%	95.50%
CHEMBL1255126	O15151	Protein Mdm4	86.31%	90.20%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.08%	99.17%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.05%	97.14%
CHEMBL340	P08684	Cytochrome P450 3A4	85.28%	91.19%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.25%	96.00%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	85.11%	89.44%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.46%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.33%	95.89%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.90%	94.08%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.24%	91.07%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.99%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.80%	97.09%
CHEMBL2535	P11166	Glucose transporter	82.09%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.12%	89.00%

Plants that contains it

• Aglaia odorata

Cross-Links

• PubChem: 85041756
• LOTUS: LTS0094181
• wikiData: Q105352734