[(3S,6S)-3-(3-hydroxy-2-phenylpropanoyl)oxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl] 3-methylbutanoate

Details

• Internal ID: c134d213-dc9e-411f-abdb-bf1bb859c27e
• Taxonomy: Alkaloids and derivatives > Tropane alkaloids
• IUPAC Name: [(3S,6S)-3-(3-hydroxy-2-phenylpropanoyl)oxy-8-methyl-8-azabicyclo[3.2.1]octan-6-yl] 3-methylbutanoate
• SMILES (Canonical): CC(C)CC(=O)OC1CC2CC(CC1N2C)OC(=O)C(CO)C3=CC=CC=C3
• SMILES (Isomeric): CC(C)CC(=O)O[C@H]1CC2C[C@@H](CC1N2C)OC(=O)C(CO)C3=CC=CC=C3
• InChI: InChI=1S/C22H31NO5/c1-14(2)9-21(25)28-20-11-16-10-17(12-19(20)23(16)3)27-22(26)18(13-24)15-7-5-4-6-8-15/h4-8,14,16-20,24H,9-13H2,1-3H3/t16?,17-,18?,19?,20-/m0/s1
• InChI Key: UOEYCNAEZZOSJM-BHZIUBDXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₁NO₅
• Molecular Weight: 389.50 g/mol
• Exact Mass: 389.22022309 g/mol
• Topological Polar Surface Area (TPSA): 76.10 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.50
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8225	82.25%
Caco-2	+	0.6106	61.06%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.4999	49.99%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9215	92.15%
OATP1B3 inhibitior	+	0.9258	92.58%
MATE1 inhibitior	-	0.8812	88.12%
OCT2 inhibitior	+	0.5750	57.50%
BSEP inhibitior	+	0.7161	71.61%
P-glycoprotein inhibitior	-	0.5754	57.54%
P-glycoprotein substrate	-	0.5241	52.41%
CYP3A4 substrate	+	0.6137	61.37%
CYP2C9 substrate	-	0.8210	82.10%
CYP2D6 substrate	-	0.6767	67.67%
CYP3A4 inhibition	-	0.8359	83.59%
CYP2C9 inhibition	-	0.9127	91.27%
CYP2C19 inhibition	-	0.9061	90.61%
CYP2D6 inhibition	-	0.8853	88.53%
CYP1A2 inhibition	-	0.9068	90.68%
CYP2C8 inhibition	-	0.9382	93.82%
CYP inhibitory promiscuity	-	0.9567	95.67%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6492	64.92%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9730	97.30%
Skin irritation	-	0.8231	82.31%
Skin corrosion	-	0.9487	94.87%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6298	62.98%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	-	0.9000	90.00%
skin sensitisation	-	0.8919	89.19%
Respiratory toxicity	+	0.9333	93.33%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.8082	80.82%
Acute Oral Toxicity (c)	III	0.7386	73.86%
Estrogen receptor binding	-	0.5908	59.08%
Androgen receptor binding	-	0.5767	57.67%
Thyroid receptor binding	-	0.5545	55.45%
Glucocorticoid receptor binding	-	0.5483	54.83%
Aromatase binding	-	0.5625	56.25%
PPAR gamma	-	0.6136	61.36%
Honey bee toxicity	-	0.8578	85.78%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5455	54.55%
Fish aquatic toxicity	+	0.8381	83.81%

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	99.01%	96.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	98.54%	94.62%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	97.42%	94.08%
CHEMBL2581	P07339	Cathepsin D	97.05%	98.95%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	96.56%	94.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.07%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	92.04%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.56%	86.33%
CHEMBL5028	O14672	ADAM10	86.83%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	82.53%	91.19%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.42%	96.47%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	81.32%	94.97%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.26%	91.11%

Plants that contains it

• Datura stramonium

Cross-Links

• PubChem: 162817078
• LOTUS: LTS0202938
• wikiData: Q105276308