3-Tropoyloxy-6-acetoxytropane

Details

• Internal ID: cc5a4a97-e81d-46a7-b3e7-cb369b157e9a
• Taxonomy: Alkaloids and derivatives > Tropane alkaloids
• IUPAC Name: [(1R,5S)-6-acetyloxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate
• SMILES (Canonical): CC(=O)OC1CC2CC(CC1N2C)OC(=O)C(CO)C3=CC=CC=C3
• SMILES (Isomeric): CC(=O)OC1C[C@H]2CC(C[C@@H]1N2C)OC(=O)C(CO)C3=CC=CC=C3
• InChI: InChI=1S/C19H25NO5/c1-12(22)24-18-9-14-8-15(10-17(18)20(14)2)25-19(23)16(11-21)13-6-4-3-5-7-13/h3-7,14-18,21H,8-11H2,1-2H3/t14-,15?,16?,17+,18?/m1/s1
• InChI Key: HMSYCWNYGYVPME-PYSDOYAXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₅NO₅
• Molecular Weight: 347.40 g/mol
• Exact Mass: 347.17327290 g/mol
• Topological Polar Surface Area (TPSA): 76.10 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.47
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• HMSYCWNYGYVPME-PYSDOYAXSA-N

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8839	88.39%
Caco-2	+	0.7317	73.17%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Lysosomes	0.5053	50.53%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9450	94.50%
OATP1B3 inhibitior	+	0.9375	93.75%
MATE1 inhibitior	-	0.8812	88.12%
OCT2 inhibitior	+	0.6250	62.50%
BSEP inhibitior	-	0.4736	47.36%
P-glycoprotein inhibitior	-	0.7891	78.91%
P-glycoprotein substrate	-	0.6400	64.00%
CYP3A4 substrate	+	0.5986	59.86%
CYP2C9 substrate	-	0.8210	82.10%
CYP2D6 substrate	-	0.6767	67.67%
CYP3A4 inhibition	-	0.8619	86.19%
CYP2C9 inhibition	-	0.9302	93.02%
CYP2C19 inhibition	-	0.9345	93.45%
CYP2D6 inhibition	-	0.9076	90.76%
CYP1A2 inhibition	-	0.9173	91.73%
CYP2C8 inhibition	-	0.9440	94.40%
CYP inhibitory promiscuity	-	0.9248	92.48%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6856	68.56%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9823	98.23%
Skin irritation	-	0.8328	83.28%
Skin corrosion	-	0.9586	95.86%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5484	54.84%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	-	0.9625	96.25%
skin sensitisation	-	0.9057	90.57%
Respiratory toxicity	+	0.9222	92.22%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.8247	82.47%
Acute Oral Toxicity (c)	III	0.7319	73.19%
Estrogen receptor binding	-	0.6899	68.99%
Androgen receptor binding	-	0.6431	64.31%
Thyroid receptor binding	-	0.6441	64.41%
Glucocorticoid receptor binding	-	0.6400	64.00%
Aromatase binding	-	0.7176	71.76%
PPAR gamma	-	0.6322	63.22%
Honey bee toxicity	-	0.8360	83.60%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5755	57.55%
Fish aquatic toxicity	+	0.6530	65.30%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	99.01%	94.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.98%	96.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	98.28%	94.08%
CHEMBL2581	P07339	Cathepsin D	97.10%	98.95%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	95.64%	94.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.53%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.21%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	87.08%	91.19%
CHEMBL5028	O14672	ADAM10	85.91%	97.50%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.42%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.72%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	80.73%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.21%	99.17%

Plants that contains it

• Datura stramonium

Cross-Links

• PubChem: 91750092
• LOTUS: LTS0206735
• wikiData: Q105030670