Eupatolide , CAS No.6750-25-0

CAS: 6750-25-0 Cat. No.: E951728 EC Number: 683-136-9 PubChem CID: 5281460

Storage

Room temperature

Specifications

Storage

Room temperature

Names and Identifiers

• Canonical Smiles: CC1=CC2C(C(CC(=CCC1)C)O)C(=C)C(=O)O2
• IUPAC Name: (3aR,4R,6E,10E,11aR)-4-hydroxy-6,10-dimethyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
• InChIKey: PDEJECFRCJOMEN-OURLZOILSA-N
• INCHI: 1S/C15H20O3/c1-9-5-4-6-10(2)8-13-14(12(16)7-9)11(3)15(17)18-13/h5,8,12-14,16H,3-4,6-7H2,1-2H3/b9-5+,10-8+/t12-,13-,14-/m1/s1
• Isomeric SMILES: C/C/1=C\[C@@H]2[C@@H]([C@@H](C/C(=C/CC1)/C)O)C(=C)C(=O)O2
• Alternate CAS: 6750-25-0
• PubChem CID: 5281460
• MeSH Entry Terms: 8beta-hydroxy-costunolide;eupatolide

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Terpene lactones
        • Level5 Sesquiterpene lactones
          • Level6 Germacranolides and derivatives

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Terpene lactones
• Intermediate Tree Nodes: Sesquiterpene lactones
• Direct Parent: Germacranolides and derivatives
• Alternative Parents: Germacrane sesquiterpenoids Gamma butyrolactones Tetrahydrofurans Enoate esters Secondary alcohols Oxacyclic compounds Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Germacranolide - Germacrane sesquiterpenoid - Sesquiterpenoid - Gamma butyrolactone - Tetrahydrofuran - Enoate ester - Alpha,beta-unsaturated carboxylic ester - Secondary alcohol - Lactone - Carboxylic acid ester - Oxacycle - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organoheterocyclic compound - Alcohol - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Carbonyl group - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.
• External Descriptors: Germacrenes

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Molecular Weight: 248.320 g/mol
• XLogP3: 1.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 248.141 Da
• Monoisotopic Mass: 248.141 Da
• Topological Polar Surface Area: 46.500 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 431.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 2
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 2
• Covalently-Bonded Unit Count: 1