2-Butenoic acid, 2-methyl-, 2,3,5,7a-tetrahydro-7-(hydroxymethyl)-1H-pyrrolizin-1-yl ester, [1S-[1alpha(Z),7aalpha]]-

Details

• Internal ID: dbddd6d3-16f2-4dfb-b8a9-36a335ef2a55
• Taxonomy: Alkaloids and derivatives
• IUPAC Name: [(1S)-7-(hydroxymethyl)-2,3,5,8-tetrahydro-1H-pyrrolizin-1-yl] (E)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CCN2C1C(=CC2)CO
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@H]1CCN2C1C(=CC2)CO
• InChI: InChI=1S/C13H19NO3/c1-3-9(2)13(16)17-11-5-7-14-6-4-10(8-15)12(11)14/h3-4,11-12,15H,5-8H2,1-2H3/b9-3+/t11-,12?/m0/s1
• InChI Key: TYGYPIIOOQNWBU-SPVDEYDNSA-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

• Heliotridine, 7-angelyl-
• Heliotridine, 7-angelate (ester)
• 2-Butenoic acid, 2-methyl-, 2,3,5,7a-tetrahydro-7-(hydroxymethyl)-1H-pyrrolizin-1-yl ester, [1S-[1.alpha.(Z),7a.alpha.]]-
• Heliotridine, 7-(2-methylcrotonate), (Z)-
• TYGYPIIOOQNWBU-SPVDEYDNSA-N
• DTXSID001019874
• 7-(Hydroxymethyl)-(1S,7aR)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl (2Z)-2-methyl-2-butenoate
• LS-47194

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9686	96.86%
Caco-2	+	0.8310	83.10%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6671	66.71%
OATP2B1 inhibitior	-	0.8578	85.78%
OATP1B1 inhibitior	+	0.9235	92.35%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8021	80.21%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	-	0.8113	81.13%
P-glycoprotein inhibitior	-	0.9669	96.69%
P-glycoprotein substrate	-	0.7257	72.57%
CYP3A4 substrate	+	0.5120	51.20%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.7533	75.33%
CYP3A4 inhibition	-	0.9646	96.46%
CYP2C9 inhibition	-	0.8902	89.02%
CYP2C19 inhibition	-	0.8878	88.78%
CYP2D6 inhibition	-	0.8283	82.83%
CYP1A2 inhibition	-	0.6621	66.21%
CYP2C8 inhibition	-	0.9461	94.61%
CYP inhibitory promiscuity	-	0.8278	82.78%
UGT catelyzed	-	0.7638	76.38%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5050	50.50%
Eye corrosion	-	0.9654	96.54%
Eye irritation	-	0.9793	97.93%
Skin irritation	-	0.7509	75.09%
Skin corrosion	-	0.8580	85.80%
Ames mutagenesis	-	0.8154	81.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5272	52.72%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	+	0.9875	98.75%
skin sensitisation	-	0.8294	82.94%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.6228	62.28%
Acute Oral Toxicity (c)	III	0.6107	61.07%
Estrogen receptor binding	-	0.9415	94.15%
Androgen receptor binding	-	0.6600	66.00%
Thyroid receptor binding	-	0.5606	56.06%
Glucocorticoid receptor binding	-	0.6066	60.66%
Aromatase binding	-	0.8409	84.09%
PPAR gamma	-	0.7875	78.75%
Honey bee toxicity	-	0.8934	89.34%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6655	66.55%
Fish aquatic toxicity	-	0.8091	80.91%

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	97.79%	96.09%
CHEMBL2581	P07339	Cathepsin D	90.93%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.07%	91.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.44%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.61%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.21%	94.45%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.19%	93.00%

Plants that contains it

• Lappula spinocarpos
• Nicotiana tabacum
• Senecio peripotamus
• Solanum tuberosum

Cross-Links

• PubChem: 6432671
• NPASS: NPC44015
• LOTUS: LTS0089996
• wikiData: Q105267313