3-(Hydroxyacetoxy)-tropane

Details

• Internal ID: 73e37910-29fe-4638-9566-a35da3f0730f
• Taxonomy: Alkaloids and derivatives > Tropane alkaloids
• IUPAC Name: [(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 2-hydroxyacetate
• SMILES (Canonical): CN1C2CCC1CC(C2)OC(=O)CO
• SMILES (Isomeric): CN1[C@@H]2CC[C@H]1CC(C2)OC(=O)CO
• InChI: InChI=1S/C10H17NO3/c1-11-7-2-3-8(11)5-9(4-7)14-10(13)6-12/h7-9,12H,2-6H2,1H3/t7-,8+,9?
• InChI Key: IAWYYJRDAMGQCB-JVHMLUBASA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₇NO₃
• Molecular Weight: 199.25 g/mol
• Exact Mass: 199.12084340 g/mol
• Topological Polar Surface Area (TPSA): 49.80 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 0.15
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 3-(Hydroxyacetoxy)-tropane
• 3a-(2'-hydroxyacetoxy)tropane
• IAWYYJRDAMGQCB-JVHMLUBASA-N

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9504	95.04%
Caco-2	+	0.8146	81.46%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Lysosomes	0.5164	51.64%
OATP2B1 inhibitior	-	0.8544	85.44%
OATP1B1 inhibitior	+	0.9589	95.89%
OATP1B3 inhibitior	+	0.9478	94.78%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	+	0.7500	75.00%
BSEP inhibitior	-	0.9386	93.86%
P-glycoprotein inhibitior	-	0.9800	98.00%
P-glycoprotein substrate	-	0.7997	79.97%
CYP3A4 substrate	+	0.5345	53.45%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6601	66.01%
CYP3A4 inhibition	-	0.9914	99.14%
CYP2C9 inhibition	-	0.9293	92.93%
CYP2C19 inhibition	-	0.9443	94.43%
CYP2D6 inhibition	-	0.9693	96.93%
CYP1A2 inhibition	-	0.9000	90.00%
CYP2C8 inhibition	-	0.9888	98.88%
CYP inhibitory promiscuity	-	0.9719	97.19%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7057	70.57%
Eye corrosion	-	0.9773	97.73%
Eye irritation	+	0.7745	77.45%
Skin irritation	-	0.7997	79.97%
Skin corrosion	-	0.9350	93.50%
Ames mutagenesis	-	0.7254	72.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6881	68.81%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.8893	88.93%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.5061	50.61%
Acute Oral Toxicity (c)	III	0.7476	74.76%
Estrogen receptor binding	-	0.8209	82.09%
Androgen receptor binding	-	0.8643	86.43%
Thyroid receptor binding	-	0.6463	64.63%
Glucocorticoid receptor binding	-	0.5108	51.08%
Aromatase binding	-	0.6829	68.29%
PPAR gamma	-	0.7637	76.37%
Honey bee toxicity	-	0.9401	94.01%
Biodegradation	+	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7455	74.55%
Fish aquatic toxicity	-	0.8839	88.39%

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	98.09%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.98%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.01%	97.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.63%	96.95%
CHEMBL340	P08684	Cytochrome P450 3A4	87.34%	91.19%
CHEMBL1899	P46098	Serotonin 3a (5-HT3a) receptor	85.81%	100.00%
CHEMBL2581	P07339	Cathepsin D	84.39%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.88%	95.89%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.48%	96.47%
CHEMBL238	Q01959	Dopamine transporter	82.14%	95.88%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.05%	99.17%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	81.10%	98.46%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.40%	94.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.25%	95.89%

Plants that contains it

• Datura stramonium

Cross-Links

• PubChem: 91750085
• LOTUS: LTS0136956
• wikiData: Q105036327