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

Details

• Internal ID: 7289e91f-9538-4154-9059-1463e6c26656
• Taxonomy: Organoheterocyclic compounds > Benzofurans > Flavaglines
• IUPAC Name: 8b-ethoxy-1-hydroxy-3a-(3-hydroxy-4-methoxyphenyl)-6,8-dimethoxy-N-methyl-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide
• SMILES (Canonical): CCOC12C(C(C(C1(OC3=C2C(=CC(=C3)OC)OC)C4=CC(=C(C=C4)OC)O)C5=CC=CC=C5)C(=O)NC)O
• SMILES (Isomeric): CCOC12C(C(C(C1(OC3=C2C(=CC(=C3)OC)OC)C4=CC(=C(C=C4)OC)O)C5=CC=CC=C5)C(=O)NC)O
• InChI: InChI=1S/C30H33NO8/c1-6-38-30-26-22(37-5)15-19(35-3)16-23(26)39-29(30,18-12-13-21(36-4)20(32)14-18)25(17-10-8-7-9-11-17)24(27(30)33)28(34)31-2/h7-16,24-25,27,32-33H,6H2,1-5H3,(H,31,34)
• InChI Key: UPPQGHKMSYMGRJ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₃NO₈
• Molecular Weight: 535.60 g/mol
• Exact Mass: 535.22061701 g/mol
• Topological Polar Surface Area (TPSA): 116.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.46
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9507	95.07%
Caco-2	-	0.6051	60.51%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6790	67.90%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8645	86.45%
OATP1B3 inhibitior	+	0.9252	92.52%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9856	98.56%
P-glycoprotein inhibitior	+	0.8735	87.35%
P-glycoprotein substrate	+	0.5723	57.23%
CYP3A4 substrate	+	0.6795	67.95%
CYP2C9 substrate	-	0.6157	61.57%
CYP2D6 substrate	-	0.7423	74.23%
CYP3A4 inhibition	+	0.5805	58.05%
CYP2C9 inhibition	+	0.5692	56.92%
CYP2C19 inhibition	-	0.5835	58.35%
CYP2D6 inhibition	-	0.8537	85.37%
CYP1A2 inhibition	+	0.5053	50.53%
CYP2C8 inhibition	+	0.8371	83.71%
CYP inhibitory promiscuity	+	0.8806	88.06%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5884	58.84%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.8933	89.33%
Skin irritation	-	0.8221	82.21%
Skin corrosion	-	0.9452	94.52%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4068	40.68%
Micronuclear	+	0.7859	78.59%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.8834	88.34%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.4573	45.73%
Acute Oral Toxicity (c)	III	0.5842	58.42%
Estrogen receptor binding	+	0.7619	76.19%
Androgen receptor binding	+	0.7881	78.81%
Thyroid receptor binding	+	0.6028	60.28%
Glucocorticoid receptor binding	+	0.7759	77.59%
Aromatase binding	-	0.5057	50.57%
PPAR gamma	+	0.7641	76.41%
Honey bee toxicity	-	0.6700	67.00%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.8628	86.28%

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	99.04%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.97%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.70%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.95%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.91%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.84%	95.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.34%	97.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.61%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.99%	92.62%
CHEMBL240	Q12809	HERG	87.26%	89.76%
CHEMBL1255126	O15151	Protein Mdm4	86.70%	90.20%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.90%	94.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.08%	96.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.93%	91.07%
CHEMBL5028	O14672	ADAM10	84.30%	97.50%
CHEMBL2535	P11166	Glucose transporter	84.29%	98.75%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	84.22%	89.44%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.93%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.28%	99.15%
CHEMBL4208	P20618	Proteasome component C5	81.99%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	81.55%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.97%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.92%	89.00%

Plants that contains it

• Aglaia odorata

Cross-Links

• PubChem: 85192469
• LOTUS: LTS0016611
• wikiData: Q105276931