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

Details

• Internal ID: 03d8566b-779a-465d-ab6d-cb028ddff4e3
• Taxonomy: Organoheterocyclic compounds > Benzofurans > Flavaglines
• IUPAC Name: 1,8b-dihydroxy-N-(4-hydroxybutyl)-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide
• SMILES (Canonical): COC1=CC=C(C=C1)C23C(C(C(C2(C4=C(O3)C=C(C=C4OC)OC)O)O)C(=O)NCCCCO)C5=CC=CC=C5
• SMILES (Isomeric): COC1=CC=C(C=C1)C23C(C(C(C2(C4=C(O3)C=C(C=C4OC)OC)O)O)C(=O)NCCCCO)C5=CC=CC=C5
• InChI: InChI=1S/C31H35NO8/c1-37-21-13-11-20(12-14-21)31-26(19-9-5-4-6-10-19)25(29(35)32-15-7-8-16-33)28(34)30(31,36)27-23(39-3)17-22(38-2)18-24(27)40-31/h4-6,9-14,17-18,25-26,28,33-34,36H,7-8,15-16H2,1-3H3,(H,32,35)
• InChI Key: OEIVNWDEYRBFIV-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₃₅NO₈
• Molecular Weight: 549.60 g/mol
• Exact Mass: 549.23626707 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.85
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9286	92.86%
Caco-2	-	0.7102	71.02%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6489	64.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8627	86.27%
OATP1B3 inhibitior	+	0.9487	94.87%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9777	97.77%
P-glycoprotein inhibitior	+	0.8385	83.85%
P-glycoprotein substrate	+	0.6452	64.52%
CYP3A4 substrate	+	0.6838	68.38%
CYP2C9 substrate	-	0.6290	62.90%
CYP2D6 substrate	-	0.7453	74.53%
CYP3A4 inhibition	-	0.5854	58.54%
CYP2C9 inhibition	-	0.7951	79.51%
CYP2C19 inhibition	-	0.7309	73.09%
CYP2D6 inhibition	-	0.7743	77.43%
CYP1A2 inhibition	-	0.7112	71.12%
CYP2C8 inhibition	+	0.7846	78.46%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6394	63.94%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9446	94.46%
Skin irritation	-	0.7782	77.82%
Skin corrosion	-	0.9373	93.73%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6616	66.16%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	-	0.6289	62.89%
skin sensitisation	-	0.8753	87.53%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.5998	59.98%
Acute Oral Toxicity (c)	III	0.6477	64.77%
Estrogen receptor binding	+	0.7452	74.52%
Androgen receptor binding	+	0.8133	81.33%
Thyroid receptor binding	+	0.5269	52.69%
Glucocorticoid receptor binding	+	0.7040	70.40%
Aromatase binding	+	0.5655	56.55%
PPAR gamma	+	0.5954	59.54%
Honey bee toxicity	-	0.8611	86.11%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6049	60.49%
Fish aquatic toxicity	-	0.4856	48.56%

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	99.26%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.04%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.59%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.25%	95.56%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	93.48%	89.44%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.03%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.30%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.20%	96.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.87%	95.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.08%	97.14%
CHEMBL340	P08684	Cytochrome P450 3A4	87.55%	91.19%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	87.51%	85.49%
CHEMBL4208	P20618	Proteasome component C5	87.21%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.75%	94.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	84.58%	89.67%
CHEMBL5028	O14672	ADAM10	83.87%	97.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.81%	91.07%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.67%	92.62%
CHEMBL240	Q12809	HERG	82.55%	89.76%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.07%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.40%	94.45%

Plants that contains it

• Aglaia elliptica

Cross-Links

• PubChem: 85056681
• LOTUS: LTS0110097
• wikiData: Q105190309