methyl (4aR,5R)-4a,5-dimethyl-6-oxo-4,5-dihydrobenzo[f][1]benzofuran-3-carboxylate

Details

• Internal ID: fc76084b-d8e6-4ae2-9f05-5374f348e123
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
• IUPAC Name: methyl (4aR,5R)-4a,5-dimethyl-6-oxo-4,5-dihydrobenzo[f][1]benzofuran-3-carboxylate
• SMILES (Canonical): CC1C(=O)C=CC2=CC3=C(CC12C)C(=CO3)C(=O)OC
• SMILES (Isomeric): C[C@H]1C(=O)C=CC2=CC3=C(C[C@]12C)C(=CO3)C(=O)OC
• InChI: InChI=1S/C16H16O4/c1-9-13(17)5-4-10-6-14-11(7-16(9,10)2)12(8-20-14)15(18)19-3/h4-6,8-9H,7H2,1-3H3/t9-,16+/m0/s1
• InChI Key: WMGPMCXBYLQVBP-XXFAHNHDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₆O₄
• Molecular Weight: 272.29 g/mol
• Exact Mass: 272.10485899 g/mol
• Topological Polar Surface Area (TPSA): 56.50 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.79
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8154	81.54%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6307	63.07%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8684	86.84%
OATP1B3 inhibitior	+	0.9441	94.41%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7584	75.84%
P-glycoprotein inhibitior	-	0.8616	86.16%
P-glycoprotein substrate	-	0.7948	79.48%
CYP3A4 substrate	+	0.6216	62.16%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8954	89.54%
CYP3A4 inhibition	-	0.6338	63.38%
CYP2C9 inhibition	-	0.6671	66.71%
CYP2C19 inhibition	-	0.7479	74.79%
CYP2D6 inhibition	-	0.9229	92.29%
CYP1A2 inhibition	+	0.7157	71.57%
CYP2C8 inhibition	-	0.6986	69.86%
CYP inhibitory promiscuity	+	0.7215	72.15%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Danger	0.4141	41.41%
Eye corrosion	-	0.9820	98.20%
Eye irritation	-	0.8985	89.85%
Skin irritation	-	0.7244	72.44%
Skin corrosion	-	0.9543	95.43%
Ames mutagenesis	-	0.6354	63.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6429	64.29%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	+	0.5915	59.15%
skin sensitisation	-	0.7306	73.06%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.5884	58.84%
Acute Oral Toxicity (c)	III	0.4569	45.69%
Estrogen receptor binding	+	0.5443	54.43%
Androgen receptor binding	+	0.6962	69.62%
Thyroid receptor binding	-	0.6164	61.64%
Glucocorticoid receptor binding	-	0.6011	60.11%
Aromatase binding	-	0.4849	48.49%
PPAR gamma	+	0.6187	61.87%
Honey bee toxicity	-	0.8519	85.19%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9974	99.74%

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	98.01%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.72%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.35%	85.14%
CHEMBL2581	P07339	Cathepsin D	88.07%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.54%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.28%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	84.10%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.48%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.48%	95.56%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.56%	94.33%
CHEMBL4208	P20618	Proteasome component C5	80.50%	90.00%

Plants that contains it

• Warburgia ugandensis

Cross-Links

• PubChem: 101289770
• LOTUS: LTS0180650
• wikiData: Q105308534