8-Episarracine

Details

• Internal ID: 39e4d2c1-58bd-4d94-81ad-0f675fd423cc
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: [(1R,8S)-7-(3-methylbut-2-enoyloxymethyl)-2,3,5,8-tetrahydro-1H-pyrrolizin-1-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CCN2C1C(=CC2)COC(=O)C=C(C)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1CCN2[C@H]1C(=CC2)COC(=O)C=C(C)C
• InChI: InChI=1S/C18H25NO4/c1-5-13(4)18(21)23-15-7-9-19-8-6-14(17(15)19)11-22-16(20)10-12(2)3/h5-6,10,15,17H,7-9,11H2,1-4H3/b13-5-/t15-,17+/m1/s1
• InChI Key: GICCIYIZUXFQFB-UYTLEXNVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₅NO₄
• Molecular Weight: 319.40 g/mol
• Exact Mass: 319.17835828 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.39
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• GICCIYIZUXFQFB-UYTLEXNVSA-N

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9609	96.09%
Caco-2	+	0.7206	72.06%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7798	77.98%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9223	92.23%
OATP1B3 inhibitior	+	0.9355	93.55%
MATE1 inhibitior	-	0.7409	74.09%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.7623	76.23%
P-glycoprotein inhibitior	-	0.5840	58.40%
P-glycoprotein substrate	-	0.5752	57.52%
CYP3A4 substrate	+	0.5963	59.63%
CYP2C9 substrate	+	0.5858	58.58%
CYP2D6 substrate	-	0.7791	77.91%
CYP3A4 inhibition	-	0.9123	91.23%
CYP2C9 inhibition	-	0.8957	89.57%
CYP2C19 inhibition	-	0.8541	85.41%
CYP2D6 inhibition	-	0.8176	81.76%
CYP1A2 inhibition	-	0.6516	65.16%
CYP2C8 inhibition	-	0.8488	84.88%
CYP inhibitory promiscuity	-	0.8664	86.64%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Danger	0.4426	44.26%
Eye corrosion	-	0.9682	96.82%
Eye irritation	-	0.9479	94.79%
Skin irritation	-	0.7650	76.50%
Skin corrosion	-	0.8973	89.73%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7758	77.58%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	+	0.9750	97.50%
skin sensitisation	-	0.8103	81.03%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.6038	60.38%
Acute Oral Toxicity (c)	III	0.6028	60.28%
Estrogen receptor binding	-	0.7947	79.47%
Androgen receptor binding	-	0.5143	51.43%
Thyroid receptor binding	-	0.5696	56.96%
Glucocorticoid receptor binding	+	0.6379	63.79%
Aromatase binding	-	0.7361	73.61%
PPAR gamma	-	0.7092	70.92%
Honey bee toxicity	-	0.8273	82.73%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6155	61.55%
Fish aquatic toxicity	-	0.4083	40.83%

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	98.64%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.41%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.43%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.36%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.18%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.07%	95.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.90%	93.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.63%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.58%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.54%	97.09%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	81.74%	97.21%
CHEMBL340	P08684	Cytochrome P450 3A4	80.54%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.32%	95.89%

Plants that contains it

• Senecio macedonicus

Cross-Links

• PubChem: 91753674
• LOTUS: LTS0186009
• wikiData: Q105008866