9-Angeloylretronecine

Details

• Internal ID: 01987d47-dea0-4209-b0c6-46bdfabab897
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: [(7R,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OCC1=CCN2C1C(CC2)O
• SMILES (Isomeric): C/C=C(/C)\C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)O
• InChI: InChI=1S/C13H19NO3/c1-3-9(2)13(16)17-8-10-4-6-14-7-5-11(15)12(10)14/h3-4,11-12,15H,5-8H2,1-2H3/b9-3-/t11-,12-/m1/s1
• InChI Key: VYUQPLFRNDQDHW-BTRLNGJCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₉NO₃
• Molecular Weight: 237.29 g/mol
• Exact Mass: 237.13649347 g/mol
• Topological Polar Surface Area (TPSA): 49.80 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.87
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• Retronecine, 7-angelate
• 9-Angeloylretronecine
• 6922-62-9
• 2-Butenoic acid, 2-methyl-, (2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl) methyl ester, (1R-(1alpha,7(Z),8beta))-
• DTXSID401314735
• (1R,7aR)-7-[[(Z)-2-Methyl-2-butenoyl]oxymethyl]-2,3,5,7a-tetrahydro-1H-pyrrolizine-1-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9786	97.86%
Caco-2	+	0.7218	72.18%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6418	64.18%
OATP2B1 inhibitior	-	0.8546	85.46%
OATP1B1 inhibitior	+	0.9127	91.27%
OATP1B3 inhibitior	+	0.9485	94.85%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.5767	57.67%
P-glycoprotein inhibitior	-	0.9672	96.72%
P-glycoprotein substrate	-	0.7331	73.31%
CYP3A4 substrate	+	0.5427	54.27%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.7146	71.46%
CYP3A4 inhibition	-	0.9271	92.71%
CYP2C9 inhibition	-	0.9141	91.41%
CYP2C19 inhibition	-	0.8979	89.79%
CYP2D6 inhibition	-	0.7925	79.25%
CYP1A2 inhibition	-	0.7192	71.92%
CYP2C8 inhibition	-	0.9192	91.92%
CYP inhibitory promiscuity	-	0.8989	89.89%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4739	47.39%
Eye corrosion	-	0.9739	97.39%
Eye irritation	-	0.9657	96.57%
Skin irritation	-	0.7579	75.79%
Skin corrosion	-	0.8713	87.13%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3887	38.87%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.9750	97.50%
skin sensitisation	-	0.8323	83.23%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.6166	61.66%
Acute Oral Toxicity (c)	III	0.6573	65.73%
Estrogen receptor binding	-	0.9296	92.96%
Androgen receptor binding	-	0.6825	68.25%
Thyroid receptor binding	-	0.7751	77.51%
Glucocorticoid receptor binding	-	0.7667	76.67%
Aromatase binding	-	0.5840	58.40%
PPAR gamma	-	0.7254	72.54%
Honey bee toxicity	-	0.8737	87.37%
Biodegradation	+	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6555	65.55%
Fish aquatic toxicity	-	0.7227	72.27%

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	98.87%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.09%	91.11%
CHEMBL2581	P07339	Cathepsin D	90.39%	98.95%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	85.10%	97.21%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.87%	93.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.12%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.47%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.04%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.60%	95.56%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.34%	85.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.25%	95.89%

Plants that contains it

• Alkanna orientalis
• Arnebia euchroma
• Cryptantha leiocarpa
• Echium glomeratum
• Eucalyptus coccifera
• Hackelia velutina
• Rhizomnium magnifolium
• Senecio hydrophilus

Cross-Links

• PubChem: 638872
• NPASS: NPC105626
• LOTUS: LTS0243284
• wikiData: Q104376002