3-Hydroxy-6-(2-methylbutyryloxy) tropane

Details

• Internal ID: 9dcb30e1-c11a-4181-b3df-9d00e6348f0e
• Taxonomy: Alkaloids and derivatives > Tropane alkaloids
• IUPAC Name: [(1S,5R)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl] 2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1CC2CC(CC1N2C)O
• SMILES (Isomeric): CCC(C)C(=O)OC1C[C@@H]2CC(C[C@H]1N2C)O
• InChI: InChI=1S/C13H23NO3/c1-4-8(2)13(16)17-12-6-9-5-10(15)7-11(12)14(9)3/h8-12,15H,4-7H2,1-3H3/t8?,9-,10?,11+,12?/m0/s1
• InChI Key: ISEGEIWRXCOCGD-IWARVNPYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₂₃NO₃
• Molecular Weight: 241.33 g/mol
• Exact Mass: 241.16779360 g/mol
• Topological Polar Surface Area (TPSA): 49.80 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.17
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9249	92.49%
Caco-2	+	0.7850	78.50%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Lysosomes	0.5544	55.44%
OATP2B1 inhibitior	-	0.8507	85.07%
OATP1B1 inhibitior	+	0.9397	93.97%
OATP1B3 inhibitior	+	0.9384	93.84%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.9184	91.84%
P-glycoprotein inhibitior	-	0.9569	95.69%
P-glycoprotein substrate	-	0.7339	73.39%
CYP3A4 substrate	+	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6994	69.94%
CYP3A4 inhibition	-	0.9704	97.04%
CYP2C9 inhibition	-	0.8759	87.59%
CYP2C19 inhibition	-	0.8897	88.97%
CYP2D6 inhibition	-	0.8300	83.00%
CYP1A2 inhibition	-	0.8314	83.14%
CYP2C8 inhibition	-	0.9740	97.40%
CYP inhibitory promiscuity	-	0.9555	95.55%
UGT catelyzed	-	0.6638	66.38%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6683	66.83%
Eye corrosion	-	0.9855	98.55%
Eye irritation	-	0.9423	94.23%
Skin irritation	-	0.7968	79.68%
Skin corrosion	-	0.9288	92.88%
Ames mutagenesis	-	0.7054	70.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.7324	73.24%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.5464	54.64%
skin sensitisation	-	0.8638	86.38%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.8099	80.99%
Acute Oral Toxicity (c)	III	0.6301	63.01%
Estrogen receptor binding	-	0.7165	71.65%
Androgen receptor binding	-	0.7175	71.75%
Thyroid receptor binding	-	0.5292	52.92%
Glucocorticoid receptor binding	-	0.5922	59.22%
Aromatase binding	-	0.8851	88.51%
PPAR gamma	-	0.8911	89.11%
Honey bee toxicity	-	0.8594	85.94%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6955	69.55%
Fish aquatic toxicity	-	0.5150	51.50%

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	98.47%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.48%	97.25%
CHEMBL2581	P07339	Cathepsin D	94.15%	98.95%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	92.73%	97.21%
CHEMBL221	P23219	Cyclooxygenase-1	90.55%	90.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.49%	96.95%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.56%	96.47%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.49%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.74%	95.89%
CHEMBL202	P00374	Dihydrofolate reductase	83.06%	89.92%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.84%	96.77%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	81.91%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.88%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	81.64%	91.19%
CHEMBL238	Q01959	Dopamine transporter	80.57%	95.88%

Plants that contains it

• Datura innoxia

Cross-Links

• PubChem: 129662820
• LOTUS: LTS0092241
• wikiData: Q105119461