Micheliolide

Details

• Internal ID: 14495ef5-d83b-49c6-8a7a-6a076bf27fba
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3aS,9R,9aS,9bS)-9-hydroxy-6,9-dimethyl-3-methylidene-4,5,7,8,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1=C2CCC(C2C3C(CC1)C(=C)C(=O)O3)(C)O
• SMILES (Isomeric): CC1=C2CC[C@@]([C@@H]2[C@@H]3[C@@H](CC1)C(=C)C(=O)O3)(C)O
• InChI: InChI=1S/C15H20O3/c1-8-4-5-11-9(2)14(16)18-13(11)12-10(8)6-7-15(12,3)17/h11-13,17H,2,4-7H2,1,3H3/t11-,12-,13-,15+/m0/s1
• InChI Key: RDJAFOWISVMOJY-PWNZVWSESA-N
• Popularity: 32 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.30

Synonyms

• 68370-47-8
• CHEBI:6922
• (3aS,9R,9aS,9bS)-9-hydroxy-6,9-dimethyl-3-methylidene-4,5,7,8,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one
• Mecheliolide
• (3aS,9R,9aS,9bS)-9-hydroxy-6,9-dimethyl-3-methylene-3a,4,5,7,8,9,9a,9b-octahydroazuleno[4,5-b]furan-2(3H)-one
• (3aS,9R,9aS,9bS,Z)-9-hydroxy-6,9-dimethyl-3-methylene-3,3a,4,5,7,8,9,9a-octahydroazuleno[4,5-b]furan-2(9bH)-one
• C09507
• CHEMBL449579
• (3aS,9R,9aS,9bS)-9-hydroxy-6,9-dimethyl-3-methylene-4,5,7,8,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one
• SCHEMBL18334099
• DTXSID20331787
• HMS3886D22
• BCP28251
• HY-N0847
• BDBM50455476
• MFCD27953044
• s9309
• AKOS030526879
• CCG-266942
• AC-33982
• AS-78222
• A867060
• Q27107361
• (3aS)-3abeta,4,5,7,8,9,9abeta,9balpha-Octahydro-9beta-hydroxy-6,9-dimethyl-3-methyleneazuleno[4,5-b]furan-2(3H)-one
• (3aS)-3ass,4,5,7,8,9,9ass,9ba-Octahydro-9ss-hydroxy-6,9-dimethyl-3-methyleneazuleno[4,5-b]furan-2(3H)-one
• (3aS,9R,9aS,9bS)-9-hydroxy-6,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,7H,8H,9H,9aH,9bH-azuleno[4,5-b]furan-2-one
• [3aS-(3aalpha,9alpha,9aalpha,9bbeta)]-3a,4,5,7,8,9,9a,9b-Octahydro-9-hydroxy-6,9-dimethyl-3-methylene-azuleno[4,5-b]furan-2(3H)-one

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
CHEMBL1075189	P14618	Pyruvate kinase isozymes M1/M2	6 nM	EC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.21%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.05%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.58%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.07%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.55%	97.25%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	86.49%	93.03%
CHEMBL4530	P00488	Coagulation factor XIII	83.80%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.57%	97.09%
CHEMBL1871	P10275	Androgen Receptor	80.41%	96.43%

Plants that contains it

• Magnolia champaca

Cross-Links

• PubChem: 442279
• LOTUS: LTS0087209
• wikiData: Q27107361