8-Methyl-6-(propionyloxy)-8-azabicyclo[3.2.1]oct-3-yl (2E)-2-methyl-2-butenoate

Details

• Internal ID: f9f49d83-46ba-45e2-bc8c-754c5c35a3e8
• Taxonomy: Alkaloids and derivatives > Tropane alkaloids
• IUPAC Name: (8-methyl-6-propanoyloxy-8-azabicyclo[3.2.1]octan-3-yl) (E)-2-methylbut-2-enoate
• InChI: InChI=1S/C16H25NO4/c1-5-10(3)16(19)20-12-7-11-8-14(21-15(18)6-2)13(9-12)17(11)4/h5,11-14H,6-9H2,1-4H3/b10-5+
• InChI Key: AUZMUMNBZCSKGT-BJMVGYQFSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₅NO₄
• Molecular Weight: 295.37 g/mol
• Exact Mass: 295.17835828 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.05
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• 8-Methyl-6-(propionyloxy)-8-azabicyclo[3.2.1]oct-3-yl (2E)-2-methyl-2-butenoate #
• 2-Butenoic acid, 2-methyl-,8-methyl-6-(1-oxopropoxy)-8-azabicyclo[3.2.1]oct-3-yl ester, [1R-[1.alpha.,3.beta.(E),5.alpha.,6.alpha.]]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9579	95.79%
Caco-2	+	0.8071	80.71%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.4973	49.73%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9141	91.41%
OATP1B3 inhibitior	+	0.9420	94.20%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.7238	72.38%
P-glycoprotein inhibitior	-	0.7819	78.19%
P-glycoprotein substrate	-	0.5253	52.53%
CYP3A4 substrate	+	0.5927	59.27%
CYP2C9 substrate	-	0.6296	62.96%
CYP2D6 substrate	-	0.8017	80.17%
CYP3A4 inhibition	-	0.9550	95.50%
CYP2C9 inhibition	-	0.8584	85.84%
CYP2C19 inhibition	-	0.8184	81.84%
CYP2D6 inhibition	-	0.8040	80.40%
CYP1A2 inhibition	-	0.7683	76.83%
CYP2C8 inhibition	-	0.9166	91.66%
CYP inhibitory promiscuity	-	0.8683	86.83%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8707	87.07%
Carcinogenicity (trinary)	Non-required	0.5987	59.87%
Eye corrosion	-	0.9828	98.28%
Eye irritation	-	0.9043	90.43%
Skin irritation	-	0.7830	78.30%
Skin corrosion	-	0.9400	94.00%
Ames mutagenesis	-	0.5954	59.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.3661	36.61%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	+	0.5216	52.16%
skin sensitisation	-	0.8668	86.68%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.5662	56.62%
Acute Oral Toxicity (c)	III	0.6293	62.93%
Estrogen receptor binding	-	0.6848	68.48%
Androgen receptor binding	-	0.8220	82.20%
Thyroid receptor binding	-	0.5278	52.78%
Glucocorticoid receptor binding	-	0.5849	58.49%
Aromatase binding	-	0.7469	74.69%
PPAR gamma	-	0.7408	74.08%
Honey bee toxicity	-	0.7696	76.96%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6855	68.55%
Fish aquatic toxicity	+	0.8474	84.74%

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	98.76%	96.09%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	96.41%	97.21%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.07%	97.25%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	94.07%	96.95%
CHEMBL2581	P07339	Cathepsin D	89.53%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	86.69%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.57%	94.45%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	84.67%	95.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.68%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.67%	89.00%
CHEMBL255	P29275	Adenosine A2b receptor	82.30%	98.59%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.65%	97.50%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.05%	96.47%

Plants that contains it

• Datura stramonium

Cross-Links

• PubChem: 5368889
• LOTUS: LTS0187954
• wikiData: Q104919246