[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: b7f8255b-892b-473f-8be7-14cf9b4eefc5
• Taxonomy: Alkaloids and derivatives > Tropane alkaloids
• IUPAC Name: [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC2CCC(C1)N2C
• SMILES (Isomeric): C/C=C(/C)\C(=O)OC1C[C@H]2CC[C@@H](C1)N2C
• InChI: InChI=1S/C13H21NO2/c1-4-9(2)13(15)16-12-7-10-5-6-11(8-12)14(10)3/h4,10-12H,5-8H2,1-3H3/b9-4-/t10-,11+,12?
• InChI Key: UVHGSMZRSVGWDJ-FMRNMKQDSA-N
• Popularity: 40 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₂₁NO₂
• Molecular Weight: 223.31 g/mol
• Exact Mass: 223.157228913 g/mol
• Topological Polar Surface Area (TPSA): 29.50 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.12
• H-Bond Acceptor: 3
• 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	+	0.9743	97.43%
Caco-2	+	0.8783	87.83%
Blood Brain Barrier	+	0.8608	86.08%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.4886	48.86%
OATP2B1 inhibitior	-	0.8566	85.66%
OATP1B1 inhibitior	+	0.9466	94.66%
OATP1B3 inhibitior	+	0.9465	94.65%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	+	0.7250	72.50%
BSEP inhibitior	-	0.9267	92.67%
P-glycoprotein inhibitior	-	0.9733	97.33%
P-glycoprotein substrate	-	0.8298	82.98%
CYP3A4 substrate	+	0.5516	55.16%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7588	75.88%
CYP3A4 inhibition	-	0.9603	96.03%
CYP2C9 inhibition	-	0.9032	90.32%
CYP2C19 inhibition	-	0.8563	85.63%
CYP2D6 inhibition	-	0.5164	51.64%
CYP1A2 inhibition	-	0.8031	80.31%
CYP2C8 inhibition	-	0.9864	98.64%
CYP inhibitory promiscuity	-	0.9097	90.97%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6221	62.21%
Eye corrosion	-	0.9718	97.18%
Eye irritation	-	0.8576	85.76%
Skin irritation	-	0.7499	74.99%
Skin corrosion	-	0.9378	93.78%
Ames mutagenesis	-	0.6354	63.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5887	58.87%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.6263	62.63%
skin sensitisation	-	0.8455	84.55%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.6214	62.14%
Acute Oral Toxicity (c)	III	0.6304	63.04%
Estrogen receptor binding	-	0.9162	91.62%
Androgen receptor binding	-	0.8910	89.10%
Thyroid receptor binding	-	0.5792	57.92%
Glucocorticoid receptor binding	-	0.8186	81.86%
Aromatase binding	-	0.7960	79.60%
PPAR gamma	-	0.7221	72.21%
Honey bee toxicity	-	0.7983	79.83%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.7455	74.55%
Fish aquatic toxicity	-	0.4568	45.68%

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	96.62%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	90.73%	91.19%
CHEMBL284	P27487	Dipeptidyl peptidase IV	90.21%	95.69%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.97%	97.25%
CHEMBL1899	P46098	Serotonin 3a (5-HT3a) receptor	89.01%	100.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	86.88%	97.21%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	85.68%	97.53%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	84.94%	97.47%
CHEMBL2581	P07339	Cathepsin D	83.43%	98.95%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.15%	96.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.92%	95.89%
CHEMBL238	Q01959	Dopamine transporter	80.48%	95.88%

Plants that contains it

• Alkekengi officinarum
• Angelica archangelica
• Angelica pubescens
• Croton tiglium
• Datura metel
• Daucus carota

Cross-Links

• PubChem: 6540490
• NPASS: NPC250042