3-Phenylacetoxy-6-hydroxytropane

Details

• Internal ID: 8fa629b9-4e71-4029-8c85-bc5c81fc3118
• Taxonomy: Alkaloids and derivatives > Tropane alkaloids
• IUPAC Name: [(1S,5S)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 2-phenylacetate
• SMILES (Canonical): CN1C2CC(CC1C(C2)O)OC(=O)CC3=CC=CC=C3
• SMILES (Isomeric): CN1[C@@H]2CC(C[C@H]1C(C2)O)OC(=O)CC3=CC=CC=C3
• InChI: InChI=1S/C16H21NO3/c1-17-12-8-13(10-14(17)15(18)9-12)20-16(19)7-11-5-3-2-4-6-11/h2-6,12-15,18H,7-10H2,1H3/t12-,13?,14+,15?/m1/s1
• InChI Key: NHJIGOBHFARUPD-JLVJUDLZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₁NO₃
• Molecular Weight: 275.34 g/mol
• Exact Mass: 275.15214353 g/mol
• Topological Polar Surface Area (TPSA): 49.80 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.37
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• NHJIGOBHFARUPD-JLVJUDLZSA-N

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9754	97.54%
Caco-2	+	0.7866	78.66%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Lysosomes	0.5519	55.19%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9231	92.31%
OATP1B3 inhibitior	+	0.9421	94.21%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	-	0.7553	75.53%
P-glycoprotein inhibitior	-	0.9368	93.68%
P-glycoprotein substrate	-	0.6094	60.94%
CYP3A4 substrate	+	0.5550	55.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4378	43.78%
CYP3A4 inhibition	-	0.9262	92.62%
CYP2C9 inhibition	-	0.9050	90.50%
CYP2C19 inhibition	-	0.9092	90.92%
CYP2D6 inhibition	-	0.8327	83.27%
CYP1A2 inhibition	-	0.8796	87.96%
CYP2C8 inhibition	-	0.9169	91.69%
CYP inhibitory promiscuity	-	0.9351	93.51%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6495	64.95%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.9337	93.37%
Skin irritation	-	0.7969	79.69%
Skin corrosion	-	0.9440	94.40%
Ames mutagenesis	-	0.7237	72.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6391	63.91%
Micronuclear	+	0.5474	54.74%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.8888	88.88%
Respiratory toxicity	+	0.9333	93.33%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.8133	81.33%
Acute Oral Toxicity (c)	III	0.6607	66.07%
Estrogen receptor binding	-	0.7557	75.57%
Androgen receptor binding	-	0.7757	77.57%
Thyroid receptor binding	-	0.7029	70.29%
Glucocorticoid receptor binding	-	0.6483	64.83%
Aromatase binding	-	0.6121	61.21%
PPAR gamma	-	0.4930	49.30%
Honey bee toxicity	-	0.9324	93.24%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	-	0.3859	38.59%

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	98.93%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.90%	98.95%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	94.43%	94.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.61%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.71%	86.33%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	86.93%	94.23%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.57%	96.95%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.41%	94.08%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.46%	97.21%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.88%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.42%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.10%	95.89%
CHEMBL5028	O14672	ADAM10	81.04%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.25%	97.09%

Plants that contains it

• Datura stramonium

Cross-Links

• PubChem: 91750089
• LOTUS: LTS0052201
• wikiData: Q105179408