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

Details

• Internal ID: 9e896bb8-7a1f-4cb8-897e-bb732b92c4de
• Taxonomy: Organoheterocyclic compounds > Benzofurans > Flavaglines
• IUPAC Name: methyl (1S,2S,3S,3aR,8bS)-1-acetyloxy-8b-hydroxy-3a-(3-hydroxy-4-methoxyphenyl)-6,8-dimethoxy-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxylate
• 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)OC
• 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)OC
• InChI: InChI=1S/C30H30O10/c1-16(31)39-27-24(28(33)38-5)25(17-9-7-6-8-10-17)30(18-11-12-21(36-3)20(32)13-18)29(27,34)26-22(37-4)14-19(35-2)15-23(26)40-30/h6-15,24-25,27,32,34H,1-5H3/t24-,25+,27-,29-,30-/m0/s1
• InChI Key: DDIJRCYLKHPKMQ-GKUJDVGKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₀O₁₀
• Molecular Weight: 550.60 g/mol
• Exact Mass: 550.18389715 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.41
• H-Bond Acceptor: 10
• 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	+	0.9777	97.77%
Caco-2	-	0.6231	62.31%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7889	78.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8808	88.08%
OATP1B3 inhibitior	-	0.2591	25.91%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9582	95.82%
P-glycoprotein inhibitior	+	0.8564	85.64%
P-glycoprotein substrate	-	0.6249	62.49%
CYP3A4 substrate	+	0.6626	66.26%
CYP2C9 substrate	-	0.5928	59.28%
CYP2D6 substrate	-	0.7926	79.26%
CYP3A4 inhibition	-	0.7104	71.04%
CYP2C9 inhibition	-	0.6344	63.44%
CYP2C19 inhibition	-	0.9277	92.77%
CYP2D6 inhibition	-	0.9337	93.37%
CYP1A2 inhibition	-	0.8991	89.91%
CYP2C8 inhibition	+	0.7973	79.73%
CYP inhibitory promiscuity	-	0.5796	57.96%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9443	94.43%
Carcinogenicity (trinary)	Danger	0.3592	35.92%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.7918	79.18%
Skin irritation	-	0.8028	80.28%
Skin corrosion	-	0.9596	95.96%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5237	52.37%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.9354	93.54%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.8062	80.62%
Acute Oral Toxicity (c)	III	0.4441	44.41%
Estrogen receptor binding	+	0.7502	75.02%
Androgen receptor binding	+	0.7822	78.22%
Thyroid receptor binding	+	0.6182	61.82%
Glucocorticoid receptor binding	+	0.7050	70.50%
Aromatase binding	-	0.5926	59.26%
PPAR gamma	+	0.7072	70.72%
Honey bee toxicity	-	0.7260	72.60%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5749	57.49%
Fish aquatic toxicity	+	0.9841	98.41%

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	98.81%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.92%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.28%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.56%	85.14%
CHEMBL2581	P07339	Cathepsin D	91.88%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.69%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	91.34%	91.19%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.58%	95.50%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	89.73%	89.44%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.03%	97.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.55%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.81%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.63%	94.45%
CHEMBL2535	P11166	Glucose transporter	86.60%	98.75%
CHEMBL1255126	O15151	Protein Mdm4	86.45%	90.20%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	85.88%	94.08%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.14%	94.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.93%	91.07%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.39%	92.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.64%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.15%	99.17%

Plants that contains it

• Aglaia odorata

Cross-Links

• PubChem: 163194971
• LOTUS: LTS0175098
• wikiData: Q104976402