[(1S,2S,3S,3aR,8bS)-2-(dimethylcarbamoyl)-8b-hydroxy-3a-(3-hydroxy-4-methoxyphenyl)-6,8-dimethoxy-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-1-yl] acetate

Details

• Internal ID: 098eee62-b02d-4f95-b4ab-44533a74bbd4
• Taxonomy: Organoheterocyclic compounds > Benzofurans > Flavaglines
• IUPAC Name: [(1S,2S,3S,3aR,8bS)-2-(dimethylcarbamoyl)-8b-hydroxy-3a-(3-hydroxy-4-methoxyphenyl)-6,8-dimethoxy-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-1-yl] acetate
• SMILES (Canonical): CC(=O)OC1C(C(C2(C1(C3=C(O2)C=C(C=C3OC)OC)O)C4=CC(=C(C=C4)OC)O)C5=CC=CC=C5)C(=O)N(C)C
• SMILES (Isomeric): CC(=O)O[C@H]1[C@H]([C@H]([C@]2([C@@]1(C3=C(O2)C=C(C=C3OC)OC)O)C4=CC(=C(C=C4)OC)O)C5=CC=CC=C5)C(=O)N(C)C
• InChI: InChI=1S/C31H33NO9/c1-17(33)40-28-25(29(35)32(2)3)26(18-10-8-7-9-11-18)31(19-12-13-22(38-5)21(34)14-19)30(28,36)27-23(39-6)15-20(37-4)16-24(27)41-31/h7-16,25-26,28,34,36H,1-6H3/t25-,26+,28-,30-,31-/m0/s1
• InChI Key: MIDNNAQHKCLBSH-YSWIADKCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₃₃NO₉
• Molecular Weight: 563.60 g/mol
• Exact Mass: 563.21553163 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 3.33
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9093	90.93%
Caco-2	-	0.6293	62.93%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6338	63.38%
OATP2B1 inhibitior	-	0.8619	86.19%
OATP1B1 inhibitior	+	0.8783	87.83%
OATP1B3 inhibitior	+	0.9097	90.97%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.9105	91.05%
P-glycoprotein inhibitior	+	0.8723	87.23%
P-glycoprotein substrate	-	0.6033	60.33%
CYP3A4 substrate	+	0.6803	68.03%
CYP2C9 substrate	+	0.6092	60.92%
CYP2D6 substrate	-	0.8034	80.34%
CYP3A4 inhibition	-	0.8120	81.20%
CYP2C9 inhibition	-	0.6941	69.41%
CYP2C19 inhibition	-	0.7335	73.35%
CYP2D6 inhibition	-	0.8907	89.07%
CYP1A2 inhibition	-	0.6969	69.69%
CYP2C8 inhibition	+	0.7276	72.76%
CYP inhibitory promiscuity	-	0.7055	70.55%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.4603	46.03%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.8517	85.17%
Skin irritation	-	0.8300	83.00%
Skin corrosion	-	0.9444	94.44%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5928	59.28%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.9067	90.67%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.6525	65.25%
Acute Oral Toxicity (c)	III	0.6033	60.33%
Estrogen receptor binding	+	0.7213	72.13%
Androgen receptor binding	+	0.7700	77.00%
Thyroid receptor binding	+	0.6144	61.44%
Glucocorticoid receptor binding	+	0.7007	70.07%
Aromatase binding	-	0.5478	54.78%
PPAR gamma	+	0.6507	65.07%
Honey bee toxicity	-	0.7183	71.83%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6404	64.04%
Fish aquatic toxicity	+	0.9632	96.32%

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	98.44%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.05%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.89%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.35%	95.56%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	93.70%	89.44%
CHEMBL340	P08684	Cytochrome P450 3A4	92.12%	91.19%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.34%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.87%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.50%	97.14%
CHEMBL1255126	O15151	Protein Mdm4	87.95%	90.20%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.72%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.27%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.05%	99.23%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.65%	94.08%
CHEMBL2535	P11166	Glucose transporter	84.01%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.64%	89.00%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	83.23%	85.49%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.07%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.75%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.67%	92.62%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.12%	93.99%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.09%	94.62%

Plants that contains it

• Aglaia odorata

Cross-Links

• PubChem: 163188407
• LOTUS: LTS0106668
• wikiData: Q105164516