[(1R,3R,5S,6R)-3-hydroxy-8-azabicyclo[3.2.1]octan-6-yl] 2-phenylacetate

Details

• Internal ID: bfa35a30-94e6-4d7a-ad46-7e2fdc982726
• Taxonomy: Alkaloids and derivatives > Tropane alkaloids
• IUPAC Name: [(1R,3R,5S,6R)-3-hydroxy-8-azabicyclo[3.2.1]octan-6-yl] 2-phenylacetate
• SMILES (Canonical): C1C2CC(C(N2)CC1O)OC(=O)CC3=CC=CC=C3
• SMILES (Isomeric): C1[C@@H]2C[C@H]([C@@H](N2)C[C@@H]1O)OC(=O)CC3=CC=CC=C3
• InChI: InChI=1S/C15H19NO3/c17-12-7-11-8-14(13(9-12)16-11)19-15(18)6-10-4-2-1-3-5-10/h1-5,11-14,16-17H,6-9H2/t11-,12-,13+,14-/m1/s1
• InChI Key: LZGZKTSKMTXSGV-YIYPIFLZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₉NO₃
• Molecular Weight: 261.32 g/mol
• Exact Mass: 261.13649347 g/mol
• Topological Polar Surface Area (TPSA): 58.60 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.03
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9691	96.91%
Caco-2	+	0.6501	65.01%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6188	61.88%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9300	93.00%
OATP1B3 inhibitior	+	0.9405	94.05%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8692	86.92%
P-glycoprotein inhibitior	-	0.9675	96.75%
P-glycoprotein substrate	-	0.7856	78.56%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.8199	81.99%
CYP2D6 substrate	+	0.3596	35.96%
CYP3A4 inhibition	-	0.9253	92.53%
CYP2C9 inhibition	-	0.8785	87.85%
CYP2C19 inhibition	-	0.8517	85.17%
CYP2D6 inhibition	-	0.8209	82.09%
CYP1A2 inhibition	-	0.9236	92.36%
CYP2C8 inhibition	-	0.6450	64.50%
CYP inhibitory promiscuity	-	0.8080	80.80%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6909	69.09%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9361	93.61%
Skin irritation	-	0.7917	79.17%
Skin corrosion	-	0.9427	94.27%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5901	59.01%
Micronuclear	+	0.7374	73.74%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.8653	86.53%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.7068	70.68%
Acute Oral Toxicity (c)	III	0.6537	65.37%
Estrogen receptor binding	-	0.6175	61.75%
Androgen receptor binding	-	0.7315	73.15%
Thyroid receptor binding	-	0.7172	71.72%
Glucocorticoid receptor binding	-	0.6171	61.71%
Aromatase binding	-	0.6775	67.75%
PPAR gamma	+	0.5708	57.08%
Honey bee toxicity	-	0.8377	83.77%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5055	50.55%
Fish aquatic toxicity	-	0.6086	60.86%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	97.28%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.10%	96.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	94.65%	94.62%
CHEMBL2581	P07339	Cathepsin D	92.73%	98.95%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	92.51%	94.23%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	91.52%	94.08%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.33%	96.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.45%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.86%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.04%	91.11%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.12%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.89%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.22%	99.17%

Plants that contains it

• Erythroxylum hypericifolium

Cross-Links

• PubChem: 11129086
• LOTUS: LTS0156225
• wikiData: Q105159865