1-O-methyl 4-O-[(1R,3R,5S,6R)-8-methyl-6-[(E)-2-methylbut-2-enoyl]oxy-8-azabicyclo[3.2.1]octan-3-yl] (E)-2-methylbut-2-enedioate

Details

• Internal ID: ea985710-aa3c-4b27-9dfb-0771636a2a1e
• Taxonomy: Alkaloids and derivatives > Tropane alkaloids
• IUPAC Name: 1-O-methyl 4-O-[(1R,3R,5S,6R)-8-methyl-6-[(E)-2-methylbut-2-enoyl]oxy-8-azabicyclo[3.2.1]octan-3-yl] (E)-2-methylbut-2-enedioate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC2CC(CC1N2C)OC(=O)C=C(C)C(=O)OC
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@@H]1C[C@H]2C[C@H](C[C@@H]1N2C)OC(=O)/C=C(\C)/C(=O)OC
• InChI: InChI=1S/C19H27NO6/c1-6-11(2)19(23)26-16-9-13-8-14(10-15(16)20(13)4)25-17(21)7-12(3)18(22)24-5/h6-7,13-16H,8-10H2,1-5H3/b11-6+,12-7+/t13-,14-,15+,16-/m1/s1
• InChI Key: HTJMXYOKUGEWDB-UWXIBPRXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₇NO₆
• Molecular Weight: 365.40 g/mol
• Exact Mass: 365.18383758 g/mol
• Topological Polar Surface Area (TPSA): 82.10 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 1.76
• H-Bond Acceptor: 7
• 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	+	0.9385	93.85%
Caco-2	+	0.6801	68.01%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.4980	49.80%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9251	92.51%
OATP1B3 inhibitior	+	0.9403	94.03%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.5116	51.16%
P-glycoprotein inhibitior	+	0.6012	60.12%
P-glycoprotein substrate	+	0.5454	54.54%
CYP3A4 substrate	+	0.6330	63.30%
CYP2C9 substrate	-	0.6104	61.04%
CYP2D6 substrate	-	0.7992	79.92%
CYP3A4 inhibition	-	0.9682	96.82%
CYP2C9 inhibition	-	0.9064	90.64%
CYP2C19 inhibition	-	0.8792	87.92%
CYP2D6 inhibition	-	0.8135	81.35%
CYP1A2 inhibition	-	0.8062	80.62%
CYP2C8 inhibition	-	0.9114	91.14%
CYP inhibitory promiscuity	-	0.9430	94.30%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8907	89.07%
Carcinogenicity (trinary)	Non-required	0.6112	61.12%
Eye corrosion	-	0.9795	97.95%
Eye irritation	-	0.9335	93.35%
Skin irritation	-	0.7738	77.38%
Skin corrosion	-	0.9402	94.02%
Ames mutagenesis	-	0.5254	52.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8076	80.76%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	-	0.5038	50.38%
skin sensitisation	-	0.8761	87.61%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.7000	70.00%
Acute Oral Toxicity (c)	III	0.6176	61.76%
Estrogen receptor binding	-	0.5535	55.35%
Androgen receptor binding	-	0.7333	73.33%
Thyroid receptor binding	+	0.5235	52.35%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.5984	59.84%
PPAR gamma	-	0.6927	69.27%
Honey bee toxicity	+	0.5510	55.10%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.7934	79.34%

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%
CHEMBL4040	P28482	MAP kinase ERK2	96.43%	83.82%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	93.89%	97.21%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.87%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	91.40%	91.19%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.26%	96.95%
CHEMBL2581	P07339	Cathepsin D	87.49%	98.95%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.65%	94.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.77%	99.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.07%	91.07%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.92%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.11%	95.89%

Plants that contains it

• Schizanthus tricolor

Cross-Links

• PubChem: 21599002
• LOTUS: LTS0232620
• wikiData: Q105033462