[(1S,3aR,4R,7aR)-3a-acetyloxy-4,7a-dimethyl-3,7-dioxo-1,4,5,6-tetrahydro-2-benzofuran-1-yl] acetate

Details

• Internal ID: a0f85ca5-7c45-4dda-9dfd-add32f14de43
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: [(1S,3aR,4R,7aR)-3a-acetyloxy-4,7a-dimethyl-3,7-dioxo-1,4,5,6-tetrahydro-2-benzofuran-1-yl] acetate
• SMILES (Canonical): CC1CCC(=O)C2(C1(C(=O)OC2OC(=O)C)OC(=O)C)C
• SMILES (Isomeric): C[C@@H]1CCC(=O)[C@@]2([C@]1(C(=O)O[C@@H]2OC(=O)C)OC(=O)C)C
• InChI: InChI=1S/C14H18O7/c1-7-5-6-10(17)13(4)12(19-8(2)15)20-11(18)14(7,13)21-9(3)16/h7,12H,5-6H2,1-4H3/t7-,12+,13+,14+/m1/s1
• InChI Key: IFRDBWYKZYXUJF-DQRILILZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₈O₇
• Molecular Weight: 298.29 g/mol
• Exact Mass: 298.10525291 g/mol
• Topological Polar Surface Area (TPSA): 96.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 0.74
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9787	97.87%
Caco-2	+	0.6486	64.86%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5932	59.32%
OATP2B1 inhibitior	-	0.8570	85.70%
OATP1B1 inhibitior	+	0.9219	92.19%
OATP1B3 inhibitior	+	0.9613	96.13%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9766	97.66%
P-glycoprotein inhibitior	-	0.7194	71.94%
P-glycoprotein substrate	-	0.8991	89.91%
CYP3A4 substrate	+	0.5857	58.57%
CYP2C9 substrate	-	0.8042	80.42%
CYP2D6 substrate	-	0.8708	87.08%
CYP3A4 inhibition	-	0.8019	80.19%
CYP2C9 inhibition	-	0.9390	93.90%
CYP2C19 inhibition	-	0.9033	90.33%
CYP2D6 inhibition	-	0.9695	96.95%
CYP1A2 inhibition	-	0.6988	69.88%
CYP2C8 inhibition	-	0.8812	88.12%
CYP inhibitory promiscuity	-	0.9624	96.24%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5641	56.41%
Eye corrosion	-	0.9619	96.19%
Eye irritation	-	0.8006	80.06%
Skin irritation	-	0.5507	55.07%
Skin corrosion	+	0.6038	60.38%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7784	77.84%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.6804	68.04%
skin sensitisation	-	0.8041	80.41%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.7206	72.06%
Acute Oral Toxicity (c)	III	0.4893	48.93%
Estrogen receptor binding	+	0.8450	84.50%
Androgen receptor binding	+	0.6017	60.17%
Thyroid receptor binding	-	0.6176	61.76%
Glucocorticoid receptor binding	-	0.6547	65.47%
Aromatase binding	-	0.6425	64.25%
PPAR gamma	-	0.6479	64.79%
Honey bee toxicity	-	0.8839	88.39%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.8580	85.80%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.07%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.63%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.97%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.61%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.58%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	87.35%	91.19%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.66%	93.04%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.35%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.29%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.63%	100.00%

Plants that contains it

• Nepeta tuberosa

Cross-Links

• PubChem: 14037485
• LOTUS: LTS0249946
• wikiData: Q105112328