7-Angeloyl-9-(hydroxypropenoyl) retronecine

Details

• Internal ID: 17ad8787-6c14-4aff-bd17-4d398dc4195a
• Taxonomy: Organoheterocyclic compounds > Pyrrolizidines
• IUPAC Name: [(1R,7S)-7-(2-hydroxyprop-2-enoyloxymethyl)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CCN2C1C(CC2)COC(=O)C(=C)O
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1CCN2C1[C@H](CC2)COC(=O)C(=C)O
• InChI: InChI=1S/C16H23NO5/c1-4-10(2)15(19)22-13-6-8-17-7-5-12(14(13)17)9-21-16(20)11(3)18/h4,12-14,18H,3,5-9H2,1-2H3/b10-4-/t12-,13-,14?/m1/s1
• InChI Key: LFJWMCVWUAPRBO-ILTOCZTMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₃NO₅
• Molecular Weight: 309.36 g/mol
• Exact Mass: 309.15762283 g/mol
• Topological Polar Surface Area (TPSA): 76.10 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 1.57
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• LFJWMCVWUAPRBO-ILTOCZTMSA-N

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8575	85.75%
Caco-2	+	0.6207	62.07%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7518	75.18%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.9300	93.00%
OATP1B3 inhibitior	+	0.9412	94.12%
MATE1 inhibitior	-	0.6809	68.09%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.8274	82.74%
P-glycoprotein inhibitior	-	0.8054	80.54%
P-glycoprotein substrate	-	0.7082	70.82%
CYP3A4 substrate	+	0.5597	55.97%
CYP2C9 substrate	-	0.5916	59.16%
CYP2D6 substrate	-	0.8041	80.41%
CYP3A4 inhibition	-	0.9307	93.07%
CYP2C9 inhibition	-	0.8668	86.68%
CYP2C19 inhibition	-	0.8729	87.29%
CYP2D6 inhibition	-	0.8428	84.28%
CYP1A2 inhibition	-	0.7281	72.81%
CYP2C8 inhibition	-	0.9022	90.22%
CYP inhibitory promiscuity	-	0.9286	92.86%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Danger	0.4657	46.57%
Eye corrosion	-	0.9719	97.19%
Eye irritation	-	0.9596	95.96%
Skin irritation	-	0.7348	73.48%
Skin corrosion	-	0.8930	89.30%
Ames mutagenesis	-	0.6354	63.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5087	50.87%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	+	0.8750	87.50%
skin sensitisation	-	0.8088	80.88%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.5145	51.45%
Acute Oral Toxicity (c)	III	0.5713	57.13%
Estrogen receptor binding	-	0.6278	62.78%
Androgen receptor binding	-	0.7678	76.78%
Thyroid receptor binding	-	0.6591	65.91%
Glucocorticoid receptor binding	+	0.6617	66.17%
Aromatase binding	-	0.5456	54.56%
PPAR gamma	-	0.6817	68.17%
Honey bee toxicity	-	0.7750	77.50%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6755	67.55%
Fish aquatic toxicity	-	0.4256	42.56%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.77%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.97%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.90%	94.45%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	90.81%	93.00%
CHEMBL2581	P07339	Cathepsin D	90.05%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.41%	95.89%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.40%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	84.64%	91.19%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.47%	94.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.93%	97.09%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.17%	93.04%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.61%	93.03%

Plants that contains it

• Alkanna orientalis

Cross-Links

• PubChem: 6429061
• LOTUS: LTS0032399
• wikiData: Q105151048