Lentiginosine

Details

• Internal ID: a452bea1-4884-437a-bfed-a278c66051d9
• Taxonomy: Organoheterocyclic compounds > Indolizidines
• IUPAC Name: (1S,2S,8aS)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,2-diol
• SMILES (Canonical): C1CCN2CC(C(C2C1)O)O
• SMILES (Isomeric): C1CCN2C[C@@H]([C@H]([C@@H]2C1)O)O
• InChI: InChI=1S/C8H15NO2/c10-7-5-9-4-2-1-3-6(9)8(7)11/h6-8,10-11H,1-5H2/t6-,7-,8-/m0/s1
• InChI Key: SQECYPINZNWUTE-FXQIFTODSA-N
• Popularity: 45 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₅NO₂
• Molecular Weight: 157.21 g/mol
• Exact Mass: 157.110278721 g/mol
• Topological Polar Surface Area (TPSA): 43.70 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -0.42
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• (1S,2S,8aS)-Octahydroindolizine-1,2-diol
• 161024-43-7
• C10155
• CHEBI:6409
• SCHEMBL1676056
• Q27107196

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9562	95.62%
Caco-2	-	0.5127	51.27%
Blood Brain Barrier	+	0.7629	76.29%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5707	57.07%
OATP2B1 inhibitior	-	0.8502	85.02%
OATP1B1 inhibitior	+	0.9726	97.26%
OATP1B3 inhibitior	+	0.9544	95.44%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.8874	88.74%
P-glycoprotein inhibitior	-	0.9864	98.64%
P-glycoprotein substrate	-	0.9026	90.26%
CYP3A4 substrate	-	0.6512	65.12%
CYP2C9 substrate	+	0.5801	58.01%
CYP2D6 substrate	+	0.6011	60.11%
CYP3A4 inhibition	-	0.9917	99.17%
CYP2C9 inhibition	-	0.9360	93.60%
CYP2C19 inhibition	-	0.9128	91.28%
CYP2D6 inhibition	-	0.8417	84.17%
CYP1A2 inhibition	-	0.7264	72.64%
CYP2C8 inhibition	-	0.9930	99.30%
CYP inhibitory promiscuity	-	0.9869	98.69%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5785	57.85%
Eye corrosion	-	0.9471	94.71%
Eye irritation	+	0.7704	77.04%
Skin irritation	-	0.5996	59.96%
Skin corrosion	-	0.6550	65.50%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6475	64.75%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	+	0.6346	63.46%
skin sensitisation	-	0.8565	85.65%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.4622	46.22%
Acute Oral Toxicity (c)	III	0.5241	52.41%
Estrogen receptor binding	-	0.9360	93.60%
Androgen receptor binding	-	0.8438	84.38%
Thyroid receptor binding	-	0.8767	87.67%
Glucocorticoid receptor binding	-	0.7867	78.67%
Aromatase binding	-	0.8951	89.51%
PPAR gamma	-	0.9081	90.81%
Honey bee toxicity	-	0.9669	96.69%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	-	0.9775	97.75%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.64%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.98%	96.09%
CHEMBL3023	Q9NRA0	Sphingosine kinase 2	87.68%	95.61%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.39%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.99%	95.89%
CHEMBL237	P41145	Kappa opioid receptor	86.95%	98.10%
CHEMBL2581	P07339	Cathepsin D	86.31%	98.95%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	85.96%	94.78%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	85.66%	96.03%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.51%	93.03%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.10%	93.04%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.47%	97.09%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	81.12%	98.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.04%	95.50%

Plants that contains it

• Arachis hypogaea
• Astragalus lentiginosus
• Glycine max

Cross-Links

• PubChem: 442645
• LOTUS: LTS0275747
• wikiData: Q105003606