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

Details

• Internal ID: e664289b-524d-42e1-a157-e016ad254f6e
• Taxonomy: Alkaloids and derivatives > Tropane alkaloids
• IUPAC Name: 1-O-methyl 4-O-[(1R,3R,5S,6R)-8-methyl-6-(3-methylbut-2-enoyloxy)-8-azabicyclo[3.2.1]octan-3-yl] (Z)-2-methylbut-2-enedioate
• SMILES (Canonical): CC(=CC(=O)OC1CC2CC(CC1N2C)OC(=O)C=C(C)C(=O)OC)C
• SMILES (Isomeric): CC(=CC(=O)O[C@@H]1C[C@H]2C[C@H](C[C@@H]1N2C)OC(=O)/C=C(/C)\C(=O)OC)C
• InChI: InChI=1S/C19H27NO6/c1-11(2)6-17(21)26-16-9-13-8-14(10-15(16)20(13)4)25-18(22)7-12(3)19(23)24-5/h6-7,13-16H,8-10H2,1-5H3/b12-7-/t13-,14-,15+,16-/m1/s1
• InChI Key: HVFPWEGSYCUCEV-YABSVOTLSA-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: 2.80
• 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	+	0.9279	92.79%
Caco-2	+	0.6674	66.74%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5735	57.35%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9435	94.35%
OATP1B3 inhibitior	+	0.9360	93.60%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.6064	60.64%
P-glycoprotein inhibitior	-	0.4467	44.67%
P-glycoprotein substrate	+	0.5601	56.01%
CYP3A4 substrate	+	0.6393	63.93%
CYP2C9 substrate	-	0.6104	61.04%
CYP2D6 substrate	-	0.7992	79.92%
CYP3A4 inhibition	-	0.9611	96.11%
CYP2C9 inhibition	-	0.8900	89.00%
CYP2C19 inhibition	-	0.8656	86.56%
CYP2D6 inhibition	-	0.8266	82.66%
CYP1A2 inhibition	-	0.8100	81.00%
CYP2C8 inhibition	-	0.9099	90.99%
CYP inhibitory promiscuity	-	0.9463	94.63%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8507	85.07%
Carcinogenicity (trinary)	Non-required	0.6165	61.65%
Eye corrosion	-	0.9785	97.85%
Eye irritation	-	0.9484	94.84%
Skin irritation	-	0.7774	77.74%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8592	85.92%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	-	0.5538	55.38%
skin sensitisation	-	0.8647	86.47%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.6248	62.48%
Acute Oral Toxicity (c)	III	0.6318	63.18%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	-	0.7487	74.87%
Thyroid receptor binding	-	0.5103	51.03%
Glucocorticoid receptor binding	-	0.4671	46.71%
Aromatase binding	-	0.5527	55.27%
PPAR gamma	-	0.6201	62.01%
Honey bee toxicity	-	0.5159	51.59%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8507	85.07%

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	98.05%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	97.79%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.79%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	91.34%	91.19%
CHEMBL2581	P07339	Cathepsin D	90.38%	98.95%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	90.12%	97.21%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.73%	96.95%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.10%	94.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.70%	99.17%
CHEMBL1899	P46098	Serotonin 3a (5-HT3a) receptor	80.68%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.28%	97.25%

Plants that contains it

• Schizanthus tricolor

Cross-Links

• PubChem: 163193002
• LOTUS: LTS0231861
• wikiData: Q105034230