Ligulolide A

Details

• Internal ID: 8cb42c92-8c77-4a94-b573-3be8574ee3dd
• Taxonomy: Organoheterocyclic compounds > Epoxides > Enol ester epoxides
• IUPAC Name: (1S,3'S,4R,4'S,5R)-3'-hydroxy-3',4',5-trimethylspiro[2,6-dioxabicyclo[3.1.0]hexane-4,2'-4,5,6,7-tetrahydroindene]-1',3-dione
• SMILES (Canonical): CC1CCCC2=C1C(C3(C2=O)C(=O)OC4C3(O4)C)(C)O
• SMILES (Isomeric): C[C@H]1CCCC2=C1[C@]([C@@]3(C2=O)C(=O)O[C@H]4[C@@]3(O4)C)(C)O
• InChI: InChI=1S/C15H18O5/c1-7-5-4-6-8-9(7)13(2,18)15(10(8)16)11(17)19-12-14(15,3)20-12/h7,12,18H,4-6H2,1-3H3/t7-,12+,13-,14-,15+/m0/s1
• InChI Key: JESVVVOFFDFWBB-PUKKRBINSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.30 g/mol
• Exact Mass: 278.11542367 g/mol
• Topological Polar Surface Area (TPSA): 76.10 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.09
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• (1S,3'S,4R,4'S,5R)-3'-Hydroxy-3',4',5-trimethylspiro[2,6-dioxabicyclo[3.1.0]hexane-4,2'-4,5,6,7-tetrahydroindene]-1',3-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9737	97.37%
Caco-2	+	0.6114	61.14%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7565	75.65%
OATP2B1 inhibitior	-	0.8533	85.33%
OATP1B1 inhibitior	+	0.9069	90.69%
OATP1B3 inhibitior	+	0.9440	94.40%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6271	62.71%
BSEP inhibitior	-	0.8170	81.70%
P-glycoprotein inhibitior	-	0.8493	84.93%
P-glycoprotein substrate	-	0.8098	80.98%
CYP3A4 substrate	+	0.5813	58.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8761	87.61%
CYP3A4 inhibition	-	0.8565	85.65%
CYP2C9 inhibition	-	0.8432	84.32%
CYP2C19 inhibition	-	0.8997	89.97%
CYP2D6 inhibition	-	0.9093	90.93%
CYP1A2 inhibition	-	0.5411	54.11%
CYP2C8 inhibition	-	0.8443	84.43%
CYP inhibitory promiscuity	-	0.9134	91.34%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4302	43.02%
Eye corrosion	-	0.9847	98.47%
Eye irritation	-	0.8780	87.80%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.8732	87.32%
Ames mutagenesis	-	0.5054	50.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.7032	70.32%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	+	0.6053	60.53%
skin sensitisation	-	0.7677	76.77%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.4149	41.49%
Estrogen receptor binding	+	0.6779	67.79%
Androgen receptor binding	+	0.6462	64.62%
Thyroid receptor binding	+	0.6104	61.04%
Glucocorticoid receptor binding	-	0.4926	49.26%
Aromatase binding	-	0.6467	64.67%
PPAR gamma	-	0.5084	50.84%
Honey bee toxicity	-	0.8457	84.57%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9706	97.06%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.34%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.83%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.58%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.96%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.06%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.99%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.76%	99.23%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.39%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.56%	89.00%
CHEMBL5255	O00206	Toll-like receptor 4	80.25%	92.50%

Plants that contains it

• Ligularia virgaurea

Cross-Links

• PubChem: 11173491
• LOTUS: LTS0021002
• wikiData: Q105126382