3-Tigloyloxy-6-hydroxytropane

Details

• Internal ID: cde80f8f-7ca7-4b70-9684-5937c83beaa1
• Taxonomy: Alkaloids and derivatives > Tropane alkaloids
• IUPAC Name: [(1R,5R)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (E)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC2CC(C(C1)N2C)O
• SMILES (Isomeric): C/C=C(\C)/C(=O)OC1C[C@H]2CC([C@@H](C1)N2C)O
• InChI: InChI=1S/C13H21NO3/c1-4-8(2)13(16)17-10-5-9-6-12(15)11(7-10)14(9)3/h4,9-12,15H,5-7H2,1-3H3/b8-4+/t9-,10?,11+,12?/m0/s1
• InChI Key: AABSYOQYJYBHOJ-IWMMXTRQSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₂₁NO₃
• Molecular Weight: 239.31 g/mol
• Exact Mass: 239.15214353 g/mol
• Topological Polar Surface Area (TPSA): 49.80 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.09
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9604	96.04%
Caco-2	+	0.7987	79.87%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.4623	46.23%
OATP2B1 inhibitior	-	0.8564	85.64%
OATP1B1 inhibitior	+	0.9306	93.06%
OATP1B3 inhibitior	+	0.9414	94.14%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.8913	89.13%
P-glycoprotein inhibitior	-	0.9673	96.73%
P-glycoprotein substrate	-	0.6916	69.16%
CYP3A4 substrate	+	0.5546	55.46%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7487	74.87%
CYP3A4 inhibition	-	0.9760	97.60%
CYP2C9 inhibition	-	0.8835	88.35%
CYP2C19 inhibition	-	0.8731	87.31%
CYP2D6 inhibition	-	0.8391	83.91%
CYP1A2 inhibition	-	0.8008	80.08%
CYP2C8 inhibition	-	0.9801	98.01%
CYP inhibitory promiscuity	-	0.9505	95.05%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6324	63.24%
Eye corrosion	-	0.9812	98.12%
Eye irritation	-	0.9557	95.57%
Skin irritation	-	0.7702	77.02%
Skin corrosion	-	0.9380	93.80%
Ames mutagenesis	-	0.5591	55.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.5469	54.69%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	+	0.5837	58.37%
skin sensitisation	-	0.8576	85.76%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.4668	46.68%
Acute Oral Toxicity (c)	III	0.5891	58.91%
Estrogen receptor binding	-	0.8840	88.40%
Androgen receptor binding	-	0.8232	82.32%
Thyroid receptor binding	-	0.5927	59.27%
Glucocorticoid receptor binding	-	0.7880	78.80%
Aromatase binding	-	0.7490	74.90%
PPAR gamma	-	0.7604	76.04%
Honey bee toxicity	-	0.7090	70.90%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	-	0.4280	42.80%

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	97.41%	96.09%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	94.89%	97.21%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.54%	96.95%
CHEMBL284	P27487	Dipeptidyl peptidase IV	90.08%	95.69%
CHEMBL340	P08684	Cytochrome P450 3A4	89.45%	91.19%
CHEMBL2581	P07339	Cathepsin D	88.79%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.42%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.27%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.82%	89.00%
CHEMBL1899	P46098	Serotonin 3a (5-HT3a) receptor	81.27%	100.00%
CHEMBL1907598	P05106	Integrin alpha-V/beta-3	81.11%	95.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.38%	95.56%

Plants that contains it

• Brugmansia arborea
• Datura innoxia
• Datura stramonium

Cross-Links

• PubChem: 129662758
• LOTUS: LTS0105677
• wikiData: Q104907803