[7-(2-methylbut-2-enoyloxy)-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl 2-(hydroxymethyl)but-2-enoate

Details

• Internal ID: f6f2011e-15cc-484b-afe9-1364797b643a
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: [7-(2-methylbut-2-enoyloxy)-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl 2-(hydroxymethyl)but-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CCN2C1C(=CC2)COC(=O)C(=CC)CO
• SMILES (Isomeric): CC=C(C)C(=O)OC1CCN2C1C(=CC2)COC(=O)C(=CC)CO
• InChI: InChI=1S/C18H25NO5/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/h4-6,15-16,20H,7-11H2,1-3H3
• InChI Key: GOENJWUGVSLZDQ-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₅NO₅
• Molecular Weight: 335.40 g/mol
• Exact Mass: 335.17327290 g/mol
• Topological Polar Surface Area (TPSA): 76.10 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.36
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9570	95.70%
Caco-2	+	0.5316	53.16%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6541	65.41%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9186	91.86%
OATP1B3 inhibitior	+	0.9387	93.87%
MATE1 inhibitior	-	0.8021	80.21%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.6301	63.01%
P-glycoprotein inhibitior	-	0.6051	60.51%
P-glycoprotein substrate	-	0.6156	61.56%
CYP3A4 substrate	+	0.5750	57.50%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.7533	75.33%
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	-	0.8174	81.74%
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	-	0.9772	97.72%
Skin irritation	-	0.7443	74.43%
Skin corrosion	-	0.9134	91.34%
Ames mutagenesis	-	0.7654	76.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7398	73.98%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	+	0.9750	97.50%
skin sensitisation	-	0.8441	84.41%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.6239	62.39%
Acute Oral Toxicity (c)	III	0.6279	62.79%
Estrogen receptor binding	-	0.7809	78.09%
Androgen receptor binding	-	0.5829	58.29%
Thyroid receptor binding	-	0.5403	54.03%
Glucocorticoid receptor binding	+	0.5559	55.59%
Aromatase binding	-	0.7001	70.01%
PPAR gamma	-	0.7290	72.90%
Honey bee toxicity	-	0.8436	84.36%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6855	68.55%
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	98.43%	96.09%
CHEMBL2581	P07339	Cathepsin D	88.70%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.19%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.21%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.10%	94.45%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.96%	93.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.77%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	82.69%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.80%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.80%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.34%	89.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.04%	95.89%

Plants that contains it

• Alkanna tinctoria
• Senecio ovatus subsp. stabianus
• Senecio triangularis

Cross-Links

• PubChem: 522876
• LOTUS: LTS0222151
• wikiData: Q105013800