[(1R,3R,5S,6R)-8-methyl-6-(3-methylbut-2-enoyloxy)-8-azabicyclo[3.2.1]octan-3-yl] (E)-4-hydroxy-3-methylbut-2-enoate

Details

• Internal ID: c543b8a2-7796-42dc-81f9-f5501dcf0978
• Taxonomy: Alkaloids and derivatives > Tropane alkaloids
• IUPAC Name: [(1R,3R,5S,6R)-8-methyl-6-(3-methylbut-2-enoyloxy)-8-azabicyclo[3.2.1]octan-3-yl] (E)-4-hydroxy-3-methylbut-2-enoate
• SMILES (Canonical): CC(=CC(=O)OC1CC2CC(CC1N2C)OC(=O)C=C(C)CO)C
• SMILES (Isomeric): CC(=CC(=O)O[C@@H]1C[C@H]2C[C@H](C[C@@H]1N2C)OC(=O)/C=C(\C)/CO)C
• InChI: InChI=1S/C18H27NO5/c1-11(2)5-17(21)24-16-8-13-7-14(9-15(16)19(13)4)23-18(22)6-12(3)10-20/h5-6,13-16,20H,7-10H2,1-4H3/b12-6+/t13-,14-,15+,16-/m1/s1
• InChI Key: IIIIUNUEKKQHPF-UMDHEIRRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₇NO₅
• Molecular Weight: 337.40 g/mol
• Exact Mass: 337.18892296 g/mol
• Topological Polar Surface Area (TPSA): 76.10 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 1.58
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8813	88.13%
Caco-2	+	0.6640	66.40%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6042	60.42%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9453	94.53%
OATP1B3 inhibitior	+	0.9338	93.38%
MATE1 inhibitior	-	0.7812	78.12%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	-	0.6801	68.01%
P-glycoprotein inhibitior	-	0.6317	63.17%
P-glycoprotein substrate	+	0.5527	55.27%
CYP3A4 substrate	+	0.6226	62.26%
CYP2C9 substrate	-	0.6083	60.83%
CYP2D6 substrate	-	0.8116	81.16%
CYP3A4 inhibition	-	0.9448	94.48%
CYP2C9 inhibition	-	0.9001	90.01%
CYP2C19 inhibition	-	0.8901	89.01%
CYP2D6 inhibition	-	0.8960	89.60%
CYP1A2 inhibition	-	0.8340	83.40%
CYP2C8 inhibition	-	0.9438	94.38%
CYP inhibitory promiscuity	-	0.9626	96.26%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9007	90.07%
Carcinogenicity (trinary)	Non-required	0.6305	63.05%
Eye corrosion	-	0.9820	98.20%
Eye irritation	-	0.9605	96.05%
Skin irritation	-	0.7667	76.67%
Skin corrosion	-	0.9285	92.85%
Ames mutagenesis	-	0.5728	57.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.5408	54.08%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.5593	55.93%
skin sensitisation	-	0.8548	85.48%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.6498	64.98%
Acute Oral Toxicity (c)	III	0.6866	68.66%
Estrogen receptor binding	+	0.6715	67.15%
Androgen receptor binding	-	0.6653	66.53%
Thyroid receptor binding	-	0.4931	49.31%
Glucocorticoid receptor binding	+	0.5859	58.59%
Aromatase binding	-	0.5839	58.39%
PPAR gamma	-	0.5618	56.18%
Honey bee toxicity	-	0.7132	71.32%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6755	67.55%
Fish aquatic toxicity	+	0.8046	80.46%

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	98.42%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	96.83%	83.82%
CHEMBL2581	P07339	Cathepsin D	95.16%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.28%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	91.21%	91.19%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.83%	97.25%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.29%	96.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.75%	99.17%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.54%	97.21%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.90%	95.89%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	82.58%	97.29%
CHEMBL3975	P09467	Fructose-1,6-bisphosphatase	80.71%	92.95%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.27%	100.00%

Plants that contains it

• Schizanthus tricolor

Cross-Links

• PubChem: 50994148
• LOTUS: LTS0242147
• wikiData: Q105113515