Barrelin

Details

• Internal ID: 311b1624-1db7-4e96-a661-cb39dec5d2c7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: 9-hydroxy-3,5a,9-trimethyl-3,3a,4,5,9a,9b-hexahydrobenzo[g][1]benzofuran-2,6-dione
• SMILES (Canonical): CC1C2CCC3(C(C2OC1=O)C(C=CC3=O)(C)O)C
• SMILES (Isomeric): CC1C2CCC3(C(C2OC1=O)C(C=CC3=O)(C)O)C
• InChI: InChI=1S/C15H20O4/c1-8-9-4-6-14(2)10(16)5-7-15(3,18)12(14)11(9)19-13(8)17/h5,7-9,11-12,18H,4,6H2,1-3H3
• InChI Key: NGPDZEACIWDCKX-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 1.20

Synonyms

• Tauremizin
• Barrelin
• Judaicin
• Judaicin (sesquiterpene)
• Tauresmin
• Tauremisin A
• 4-Epipallensin
• SCHEMBL3353829
• NGPDZEACIWDCKX-UHFFFAOYSA-N
• (3S,3aS,5aR,9S,9aR,9bS)-9-hydroxy-3,5a,9-Trimethyl-3a,4,5,5a,9,9a-hexahydronaphtho[1,2-b]furan-2,6(3H,9bH)-dione
• Naphtho[1,2-b]furan-2,6(3H,4H)-dione, 3a,5,5a,9,9a,9b-hexahydro-9-hydroxy-3,5a,9-trimethyl-, (3S,3aS,5aR,9S,9aR,9bS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	177.8 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.56%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.31%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.97%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.49%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.46%	95.56%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	87.32%	86.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.01%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.36%	97.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.23%	94.80%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.48%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.95%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.59%	89.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.39%	93.04%

Plants that contains it

• Achillea millefolium
• Artemisia abyssinica
• Artemisia cana
• Artemisia judaica
• Artemisia ludoviciana
• Artemisia pallens
• Echinops ritro
• Xanthium strumarium

Cross-Links

• PubChem: 619337
• LOTUS: LTS0070208
• wikiData: Q105179077