[(1R,2S,8S)-1-(hydroxymethyl)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-2-yl] 3-methylbut-2-enoate

Details

• Internal ID: c0363fe0-bff6-4d0a-ba0f-eac9444a63b4
• Taxonomy: Organoheterocyclic compounds > Pyrrolizidines
• IUPAC Name: [(1R,2S,8S)-1-(hydroxymethyl)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-2-yl] 3-methylbut-2-enoate
• SMILES (Canonical): CC(=CC(=O)OC1CN2CCCC2C1CO)C
• SMILES (Isomeric): CC(=CC(=O)O[C@@H]1CN2CCC[C@H]2[C@@H]1CO)C
• InChI: InChI=1S/C13H21NO3/c1-9(2)6-13(16)17-12-7-14-5-3-4-11(14)10(12)8-15/h6,10-12,15H,3-5,7-8H2,1-2H3/t10-,11-,12+/m0/s1
• InChI Key: UHKCBOUTGLEVSZ-SDDRHHMPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₂₁NO₃
• Molecular Weight: 239.31 g/mol
• Exact Mass: 239.15214353 g/mol
• Topological Polar Surface Area (TPSA): 49.80 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 0.95
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9627	96.27%
Caco-2	+	0.7778	77.78%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7542	75.42%
OATP2B1 inhibitior	-	0.8569	85.69%
OATP1B1 inhibitior	+	0.9371	93.71%
OATP1B3 inhibitior	+	0.9426	94.26%
MATE1 inhibitior	-	0.8221	82.21%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	-	0.6530	65.30%
P-glycoprotein inhibitior	-	0.9628	96.28%
P-glycoprotein substrate	-	0.7273	72.73%
CYP3A4 substrate	+	0.5315	53.15%
CYP2C9 substrate	-	0.6085	60.85%
CYP2D6 substrate	-	0.8088	80.88%
CYP3A4 inhibition	-	0.9790	97.90%
CYP2C9 inhibition	-	0.9036	90.36%
CYP2C19 inhibition	-	0.8920	89.20%
CYP2D6 inhibition	-	0.8273	82.73%
CYP1A2 inhibition	-	0.6936	69.36%
CYP2C8 inhibition	-	0.9683	96.83%
CYP inhibitory promiscuity	-	0.8486	84.86%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4548	45.48%
Eye corrosion	-	0.9700	97.00%
Eye irritation	-	0.9420	94.20%
Skin irritation	-	0.7427	74.27%
Skin corrosion	-	0.8742	87.42%
Ames mutagenesis	-	0.7382	73.82%
Human Ether-a-go-go-Related Gene inhibition	-	0.5111	51.11%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	+	0.7088	70.88%
skin sensitisation	-	0.8332	83.32%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.6585	65.85%
Acute Oral Toxicity (c)	III	0.5813	58.13%
Estrogen receptor binding	-	0.8633	86.33%
Androgen receptor binding	-	0.6402	64.02%
Thyroid receptor binding	-	0.7050	70.50%
Glucocorticoid receptor binding	-	0.4911	49.11%
Aromatase binding	-	0.9161	91.61%
PPAR gamma	-	0.7915	79.15%
Honey bee toxicity	-	0.8924	89.24%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6155	61.55%
Fish aquatic toxicity	-	0.6541	65.41%

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	96.28%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.94%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.60%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.75%	97.25%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.62%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.00%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.13%	97.09%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.12%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	82.08%	91.19%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.53%	94.33%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	80.87%	96.03%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.02%	95.89%

Plants that contains it

• Senecio caudatus

Cross-Links

• PubChem: 162963762
• LOTUS: LTS0000874
• wikiData: Q105272928