[(1S,7R)-7-[(E)-2-methylbut-2-enoyl]oxy-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-yl]methyl (Z)-2-(hydroxymethyl)but-2-enoate

Details

• Internal ID: 8dc7fe16-7e41-49f1-9ea9-032c277e458b
• Taxonomy: Organoheterocyclic compounds > Pyrrolizidines
• IUPAC Name: [(1S,7R)-7-[(E)-2-methylbut-2-enoyl]oxy-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-yl]methyl (Z)-2-(hydroxymethyl)but-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CCN2C1C(CC2)COC(=O)C(=CC)CO
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@@H]1CCN2C1[C@H](CC2)COC(=O)/C(=C\C)/CO
• InChI: InChI=1S/C18H27NO5/c1-4-12(3)17(21)24-15-7-9-19-8-6-14(16(15)19)11-23-18(22)13(5-2)10-20/h4-5,14-16,20H,6-11H2,1-3H3/b12-4+,13-5-/t14-,15-,16?/m1/s1
• InChI Key: YMUQRQKYYOWGPN-VVWDSEOUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₇NO₅
• Molecular Weight: 337.40 g/mol
• Exact Mass: 337.18892296 g/mol
• Topological Polar Surface Area (TPSA): 76.10 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.44
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• YMUQRQKYYOWGPN-VVWDSEOUSA-N

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9570	95.70%
Caco-2	+	0.6472	64.72%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6541	65.41%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9346	93.46%
OATP1B3 inhibitior	+	0.9387	93.87%
MATE1 inhibitior	-	0.8221	82.21%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.4914	49.14%
P-glycoprotein inhibitior	-	0.5162	51.62%
P-glycoprotein substrate	-	0.5936	59.36%
CYP3A4 substrate	+	0.5611	56.11%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.7702	77.02%
CYP3A4 inhibition	-	0.9390	93.90%
CYP2C9 inhibition	-	0.9387	93.87%
CYP2C19 inhibition	-	0.9253	92.53%
CYP2D6 inhibition	-	0.8408	84.08%
CYP1A2 inhibition	-	0.7426	74.26%
CYP2C8 inhibition	-	0.8881	88.81%
CYP inhibitory promiscuity	-	0.9625	96.25%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Danger	0.5154	51.54%
Eye corrosion	-	0.9745	97.45%
Eye irritation	-	0.9723	97.23%
Skin irritation	-	0.7443	74.43%
Skin corrosion	-	0.9134	91.34%
Ames mutagenesis	-	0.6954	69.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4146	41.46%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	+	1.0000	100.00%
skin sensitisation	-	0.8441	84.41%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.6010	60.10%
Acute Oral Toxicity (c)	III	0.6279	62.79%
Estrogen receptor binding	-	0.6815	68.15%
Androgen receptor binding	-	0.6930	69.30%
Thyroid receptor binding	-	0.5969	59.69%
Glucocorticoid receptor binding	-	0.5952	59.52%
Aromatase binding	-	0.7647	76.47%
PPAR gamma	-	0.7490	74.90%
Honey bee toxicity	-	0.7853	78.53%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7255	72.55%
Fish aquatic toxicity	-	0.6027	60.27%

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	97.97%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.97%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	92.20%	83.82%
CHEMBL2581	P07339	Cathepsin D	89.05%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.95%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.54%	97.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.94%	93.00%
CHEMBL228	P31645	Serotonin transporter	85.75%	95.51%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.63%	93.04%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.30%	91.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.28%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.73%	94.33%
CHEMBL340	P08684	Cytochrome P450 3A4	83.59%	91.19%

Plants that contains it

• Senecio hydrophilus

Cross-Links

• PubChem: 6428030
• LOTUS: LTS0158751
• wikiData: Q105350755