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

Details

• Internal ID: 1e5879d1-3dfc-4576-92fe-17e5ebf3ff9d
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: [(7R,8R)-7-(3-methylbut-2-enoyloxy)-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (Z)-2-(hydroxymethyl)but-2-enoate
• SMILES (Canonical): CC=C(CO)C(=O)OCC1=CCN2C1C(CC2)OC(=O)C=C(C)C
• SMILES (Isomeric): C/C=C(/CO)\C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)OC(=O)C=C(C)C
• InChI: InChI=1S/C18H25NO5/c1-4-13(10-20)18(22)23-11-14-5-7-19-8-6-15(17(14)19)24-16(21)9-12(2)3/h4-5,9,15,17,20H,6-8,10-11H2,1-3H3/b13-4-/t15-,17-/m1/s1
• InChI Key: MMQLVYYYZSPCSB-BTXCVJGZSA-N
• Popularity: 0 references 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: 1.20
• 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	+	0.9539	95.39%
Caco-2	+	0.5844	58.44%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7164	71.64%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9230	92.30%
OATP1B3 inhibitior	+	0.9334	93.34%
MATE1 inhibitior	-	0.8021	80.21%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.6674	66.74%
P-glycoprotein inhibitior	-	0.5870	58.70%
P-glycoprotein substrate	-	0.5000	50.00%
CYP3A4 substrate	+	0.6005	60.05%
CYP2C9 substrate	-	0.8075	80.75%
CYP2D6 substrate	-	0.7935	79.35%
CYP3A4 inhibition	-	0.9559	95.59%
CYP2C9 inhibition	-	0.9303	93.03%
CYP2C19 inhibition	-	0.9144	91.44%
CYP2D6 inhibition	-	0.8500	85.00%
CYP1A2 inhibition	-	0.7558	75.58%
CYP2C8 inhibition	-	0.7695	76.95%
CYP inhibitory promiscuity	-	0.9663	96.63%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Danger	0.5053	50.53%
Eye corrosion	-	0.9731	97.31%
Eye irritation	-	0.9652	96.52%
Skin irritation	-	0.7420	74.20%
Skin corrosion	-	0.9036	90.36%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4275	42.75%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	+	0.9625	96.25%
skin sensitisation	-	0.8296	82.96%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.5177	51.77%
Acute Oral Toxicity (c)	III	0.6371	63.71%
Estrogen receptor binding	-	0.6344	63.44%
Androgen receptor binding	-	0.5105	51.05%
Thyroid receptor binding	-	0.5612	56.12%
Glucocorticoid receptor binding	+	0.6216	62.16%
Aromatase binding	-	0.5588	55.88%
PPAR gamma	-	0.5973	59.73%
Honey bee toxicity	-	0.8114	81.14%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6455	64.55%
Fish aquatic toxicity	-	0.5141	51.41%

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	98.80%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.80%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.26%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.13%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.67%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.90%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.15%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.00%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.51%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.02%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	81.72%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.51%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.18%	95.89%

Plants that contains it

• Senecio cacaliaster
• Senecio variabilis

Cross-Links

• PubChem: 162912234
• LOTUS: LTS0166931
• wikiData: Q105167991