(1R,2S,3S,5R)-8-azabicyclo[3.2.1]octane-1,2,3-triol

Details

• Internal ID: 59c15b28-b37f-4d12-bc82-2fff3af4e937
• Taxonomy: Alkaloids and derivatives > Tropane alkaloids
• IUPAC Name: (1R,2S,3S,5R)-8-azabicyclo[3.2.1]octane-1,2,3-triol
• SMILES (Canonical): C1CC2(C(C(CC1N2)O)O)O
• SMILES (Isomeric): C1C[C@]2([C@H]([C@H](C[C@@H]1N2)O)O)O
• InChI: InChI=1S/C7H13NO3/c9-5-3-4-1-2-7(11,8-4)6(5)10/h4-6,8-11H,1-3H2/t4-,5+,6+,7-/m1/s1
• InChI Key: XOCBOVUINUHZJA-JRTVQGFMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₇H₁₃NO₃
• Molecular Weight: 159.18 g/mol
• Exact Mass: 159.08954328 g/mol
• Topological Polar Surface Area (TPSA): 72.70 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -1.45
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7106	71.06%
Caco-2	-	0.9148	91.48%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6486	64.86%
OATP2B1 inhibitior	-	0.8508	85.08%
OATP1B1 inhibitior	+	0.9627	96.27%
OATP1B3 inhibitior	+	0.9511	95.11%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9463	94.63%
P-glycoprotein inhibitior	-	0.9838	98.38%
P-glycoprotein substrate	-	0.8219	82.19%
CYP3A4 substrate	-	0.5543	55.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7594	75.94%
CYP3A4 inhibition	-	0.9960	99.60%
CYP2C9 inhibition	-	0.9430	94.30%
CYP2C19 inhibition	-	0.8903	89.03%
CYP2D6 inhibition	-	0.9310	93.10%
CYP1A2 inhibition	-	0.9214	92.14%
CYP2C8 inhibition	-	0.9653	96.53%
CYP inhibitory promiscuity	-	0.9779	97.79%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6798	67.98%
Eye corrosion	-	0.9755	97.55%
Eye irritation	-	0.7262	72.62%
Skin irritation	-	0.7477	74.77%
Skin corrosion	-	0.8997	89.97%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6766	67.66%
Micronuclear	+	0.5400	54.00%
Hepatotoxicity	+	0.5792	57.92%
skin sensitisation	-	0.8487	84.87%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.5976	59.76%
Acute Oral Toxicity (c)	III	0.5940	59.40%
Estrogen receptor binding	-	0.7874	78.74%
Androgen receptor binding	-	0.7057	70.57%
Thyroid receptor binding	-	0.7235	72.35%
Glucocorticoid receptor binding	-	0.7319	73.19%
Aromatase binding	-	0.8200	82.00%
PPAR gamma	-	0.7475	74.75%
Honey bee toxicity	-	0.8967	89.67%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	-	0.9654	96.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL226	P30542	Adenosine A1 receptor	94.04%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.00%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.15%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.11%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.53%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	89.74%	94.75%
CHEMBL238	Q01959	Dopamine transporter	88.73%	95.88%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.53%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.42%	82.69%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	81.22%	95.58%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.87%	92.94%
CHEMBL299	P17252	Protein kinase C alpha	80.65%	98.03%
CHEMBL213	P08588	Beta-1 adrenergic receptor	80.29%	95.56%

Plants that contains it

• Ipomoea batatas
• Mandragora officinarum

Cross-Links

• PubChem: 14608506
• LOTUS: LTS0033551
• wikiData: Q105337679