dimethyl (4R,4aR,7R,7aS)-4a,7-dimethyl-5,6,7,8-tetrahydro-4H-cyclopenta[f][1]benzofuran-4,7a-dicarboxylate

Details

• Internal ID: 44a0632f-4f3e-46b1-9e8e-51af63ad6647
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: dimethyl (4R,4aR,7R,7aS)-4a,7-dimethyl-5,6,7,8-tetrahydro-4H-cyclopenta[f][1]benzofuran-4,7a-dicarboxylate
• SMILES (Canonical): CC1CCC2(C1(CC3=C(C2C(=O)OC)C=CO3)C(=O)OC)C
• SMILES (Isomeric): C[C@@H]1CC[C@]2([C@@]1(CC3=C([C@@H]2C(=O)OC)C=CO3)C(=O)OC)C
• InChI: InChI=1S/C17H22O5/c1-10-5-7-16(2)13(14(18)20-3)11-6-8-22-12(11)9-17(10,16)15(19)21-4/h6,8,10,13H,5,7,9H2,1-4H3/t10-,13-,16-,17-/m1/s1
• InChI Key: NWEBPPVRKQYLGF-FPOOMLEOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.40 g/mol
• Exact Mass: 306.14672380 g/mol
• Topological Polar Surface Area (TPSA): 65.70 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.69
• H-Bond Acceptor: 5
• 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	+	0.9883	98.83%
Caco-2	+	0.7495	74.95%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7177	71.77%
OATP2B1 inhibitior	-	0.8573	85.73%
OATP1B1 inhibitior	+	0.8912	89.12%
OATP1B3 inhibitior	+	0.9652	96.52%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.9050	90.50%
P-glycoprotein inhibitior	-	0.7322	73.22%
P-glycoprotein substrate	-	0.7614	76.14%
CYP3A4 substrate	+	0.6508	65.08%
CYP2C9 substrate	-	0.7874	78.74%
CYP2D6 substrate	-	0.8169	81.69%
CYP3A4 inhibition	-	0.7561	75.61%
CYP2C9 inhibition	-	0.7786	77.86%
CYP2C19 inhibition	-	0.8104	81.04%
CYP2D6 inhibition	-	0.9558	95.58%
CYP1A2 inhibition	-	0.7011	70.11%
CYP2C8 inhibition	-	0.5939	59.39%
CYP inhibitory promiscuity	-	0.8738	87.38%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7700	77.00%
Carcinogenicity (trinary)	Non-required	0.6395	63.95%
Eye corrosion	-	0.9809	98.09%
Eye irritation	-	0.8424	84.24%
Skin irritation	-	0.7687	76.87%
Skin corrosion	-	0.9508	95.08%
Ames mutagenesis	-	0.6970	69.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4251	42.51%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.5834	58.34%
skin sensitisation	-	0.8511	85.11%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6181	61.81%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.6707	67.07%
Acute Oral Toxicity (c)	III	0.5210	52.10%
Estrogen receptor binding	-	0.5421	54.21%
Androgen receptor binding	+	0.6845	68.45%
Thyroid receptor binding	-	0.6390	63.90%
Glucocorticoid receptor binding	-	0.6892	68.92%
Aromatase binding	-	0.6560	65.60%
PPAR gamma	-	0.5550	55.50%
Honey bee toxicity	-	0.8539	85.39%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9895	98.95%

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	97.83%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.74%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.71%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	83.77%	91.19%
CHEMBL2581	P07339	Cathepsin D	83.03%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.30%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.26%	91.07%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.99%	95.56%

Plants that contains it

• Porella grandiloba

Cross-Links

• PubChem: 162955358
• LOTUS: LTS0238863
• wikiData: Q105186554