3-Tigloyloxy-6-(2-methyl-butyryloxy)-tropane

Details

• Internal ID: a6c29f57-6202-4c98-9c56-7c96b02038a1
• Taxonomy: Alkaloids and derivatives > Tropane alkaloids
• IUPAC Name: [(1S,5R)-8-methyl-3-[(E)-2-methylbut-2-enoyl]oxy-8-azabicyclo[3.2.1]octan-6-yl] 2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1CC2CC(CC1N2C)OC(=O)C(=CC)C
• SMILES (Isomeric): CCC(C)C(=O)OC1C[C@@H]2CC(C[C@H]1N2C)OC(=O)/C(=C/C)/C
• InChI: InChI=1S/C18H29NO4/c1-6-11(3)17(20)22-14-8-13-9-16(15(10-14)19(13)5)23-18(21)12(4)7-2/h6,12-16H,7-10H2,1-5H3/b11-6+/t12?,13-,14?,15+,16?/m0/s1
• InChI Key: LWJJYAYQOTXATC-FVOVJAJASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₉NO₄
• Molecular Weight: 323.40 g/mol
• Exact Mass: 323.20965841 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 2.69
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9587	95.87%
Caco-2	+	0.7600	76.00%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.4737	47.37%
OATP2B1 inhibitior	-	0.8579	85.79%
OATP1B1 inhibitior	+	0.9047	90.47%
OATP1B3 inhibitior	+	0.9414	94.14%
MATE1 inhibitior	-	0.6600	66.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.6412	64.12%
P-glycoprotein inhibitior	-	0.6688	66.88%
P-glycoprotein substrate	-	0.5756	57.56%
CYP3A4 substrate	+	0.5806	58.06%
CYP2C9 substrate	-	0.6262	62.62%
CYP2D6 substrate	-	0.8141	81.41%
CYP3A4 inhibition	-	0.9564	95.64%
CYP2C9 inhibition	-	0.8549	85.49%
CYP2C19 inhibition	-	0.8035	80.35%
CYP2D6 inhibition	-	0.8134	81.34%
CYP1A2 inhibition	-	0.7646	76.46%
CYP2C8 inhibition	-	0.9188	91.88%
CYP inhibitory promiscuity	-	0.8696	86.96%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8807	88.07%
Carcinogenicity (trinary)	Non-required	0.5894	58.94%
Eye corrosion	-	0.9836	98.36%
Eye irritation	-	0.9393	93.93%
Skin irritation	-	0.7721	77.21%
Skin corrosion	-	0.9351	93.51%
Ames mutagenesis	-	0.6054	60.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6400	64.00%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.6692	66.92%
skin sensitisation	-	0.8624	86.24%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.6723	67.23%
Acute Oral Toxicity (c)	III	0.6450	64.50%
Estrogen receptor binding	-	0.5196	51.96%
Androgen receptor binding	-	0.6959	69.59%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.5336	53.36%
Aromatase binding	-	0.6694	66.94%
PPAR gamma	-	0.7433	74.33%
Honey bee toxicity	-	0.7824	78.24%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7755	77.55%
Fish aquatic toxicity	+	0.9159	91.59%

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	98.85%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.28%	97.25%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	95.05%	97.21%
CHEMBL2581	P07339	Cathepsin D	93.97%	98.95%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.15%	96.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.06%	94.45%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.31%	96.47%
CHEMBL340	P08684	Cytochrome P450 3A4	85.49%	91.19%
CHEMBL284	P27487	Dipeptidyl peptidase IV	84.77%	95.69%
CHEMBL202	P00374	Dihydrofolate reductase	83.77%	89.92%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	83.42%	97.50%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.32%	95.17%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.38%	89.50%

Plants that contains it

• Datura innoxia

Cross-Links

• PubChem: 129662818
• LOTUS: LTS0260618
• wikiData: Q105158346