[(1R,8R)-7-[[(Z)-2-methylbut-2-enoyl]oxymethyl]-2,3,5,8-tetrahydro-1H-pyrrolizin-1-yl] (Z)-4-hydroxy-3-methylbut-2-enoate

Details

• Internal ID: 081a668f-c5ef-4e76-bd7a-6e4fcaafd50b
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: [(1R,8R)-7-[[(Z)-2-methylbut-2-enoyl]oxymethyl]-2,3,5,8-tetrahydro-1H-pyrrolizin-1-yl] (Z)-4-hydroxy-3-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OCC1=CCN2C1C(CC2)OC(=O)C=C(C)CO
• SMILES (Isomeric): C/C=C(/C)\C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)OC(=O)/C=C(/C)\CO
• InChI: InChI=1S/C18H25NO5/c1-4-13(3)18(22)23-11-14-5-7-19-8-6-15(17(14)19)24-16(21)9-12(2)10-20/h4-5,9,15,17,20H,6-8,10-11H2,1-3H3/b12-9-,13-4-/t15-,17-/m1/s1
• InChI Key: GAQBTEYEZLKELC-KPKMGULASA-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	+	0.9123	91.23%
Caco-2	+	0.6267	62.67%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6453	64.53%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9139	91.39%
OATP1B3 inhibitior	+	0.9378	93.78%
MATE1 inhibitior	-	0.8021	80.21%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.6475	64.75%
P-glycoprotein inhibitior	-	0.6185	61.85%
P-glycoprotein substrate	-	0.5537	55.37%
CYP3A4 substrate	+	0.6257	62.57%
CYP2C9 substrate	-	0.8075	80.75%
CYP2D6 substrate	-	0.7935	79.35%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.9324	93.24%
CYP2C19 inhibition	-	0.9023	90.23%
CYP2D6 inhibition	-	0.8332	83.32%
CYP1A2 inhibition	-	0.7554	75.54%
CYP2C8 inhibition	-	0.8046	80.46%
CYP inhibitory promiscuity	-	0.9409	94.09%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Danger	0.4726	47.26%
Eye corrosion	-	0.9745	97.45%
Eye irritation	-	0.9729	97.29%
Skin irritation	-	0.7535	75.35%
Skin corrosion	-	0.9081	90.81%
Ames mutagenesis	-	0.7154	71.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4099	40.99%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	+	0.9625	96.25%
skin sensitisation	-	0.8347	83.47%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.6469	64.69%
Acute Oral Toxicity (c)	III	0.6783	67.83%
Estrogen receptor binding	-	0.6291	62.91%
Androgen receptor binding	-	0.4850	48.50%
Thyroid receptor binding	-	0.5865	58.65%
Glucocorticoid receptor binding	+	0.6639	66.39%
Aromatase binding	-	0.6273	62.73%
PPAR gamma	-	0.5163	51.63%
Honey bee toxicity	-	0.8030	80.30%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6055	60.55%
Fish aquatic toxicity	-	0.5644	56.44%

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	98.57%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.70%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.40%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.42%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.02%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.53%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	84.67%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.67%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.17%	97.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.17%	93.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.12%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.73%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.66%	100.00%

Plants that contains it

• Senecio cacaliaster

Cross-Links

• PubChem: 162939372
• LOTUS: LTS0209445
• wikiData: Q105005566