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Record Information
Version2.0
Created at2022-04-28 21:59:20 UTC
Updated at2022-04-28 21:59:20 UTC
NP-MRD IDNP0076797
Secondary Accession NumbersNone
Natural Product Identification
Common NameLoxothyrin A
Description[(1S,1'R,2S,5R,6R,6'R,7'R,9'R)-2-(acetyloxy)-6-formyl-7'-hydroxy-5-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]Dodecane]-5-yl]methyl acetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Loxothyrin A is found in Isodon japonicus, Isodon loxothyrsa and Isodon loxothyrsus. Based on a literature review very few articles have been published on [(1S,1'R,2S,5R,6R,6'R,7'R,9'R)-2-(acetyloxy)-6-formyl-7'-hydroxy-5-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]Dodecane]-5-yl]methyl acetate.
Structure
Thumb
Synonyms
ValueSource
[(1S,1'r,2S,5R,6R,6'r,7'r,9'r)-2-(Acetyloxy)-6-formyl-7'-hydroxy-5-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0,]dodecane]-5-yl]methyl acetic acidGenerator
Chemical FormulaC24H30O9
Average Mass462.4950 Da
Monoisotopic Mass462.18898 Da
IUPAC Name[(1S,1'R,2S,5R,6R,6'R,7'R,9'R)-2-(acetyloxy)-6-formyl-7'-hydroxy-5-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0^{1,6}]dodecane]-5-yl]methyl acetate
Traditional Name(1S,1'R,2S,5R,6R,6'R,7'R,9'R)-2-(acetyloxy)-6-formyl-7'-hydroxy-5-methyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0^{1,6}]dodecane]-5-ylmethyl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)OC[C@]1(C)CC[C@H](OC(C)=O)[C@]2(COC(=O)[C@]34C[C@H](C[C@@H](O)[C@H]23)C(=C)C4=O)[C@@H]1C=O
InChI Identifier
InChI=1S/C24H30O9/c1-12-15-7-16(28)19-23(8-15,20(12)29)21(30)32-11-24(19)17(9-25)22(4,10-31-13(2)26)6-5-18(24)33-14(3)27/h9,15-19,28H,1,5-8,10-11H2,2-4H3/t15-,16+,17+,18-,19-,22-,23+,24-/m0/s1
InChI KeyDESXTEYYECQGPC-QVCHTXSKSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Isodon japonicusPlant
Isodon loxothyrsaPlant
Isodon loxothyrsusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentDiterpene lactones
Alternative Parents
Substituents
  • Kaurane diterpenoid
  • Diterpenoid
  • Diterpene lactone
  • Tricarboxylic acid or derivatives
  • Delta_valerolactone
  • Delta valerolactone
  • Oxane
  • Cyclic alcohol
  • Secondary alcohol
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1ALOGPS
logP0.34ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)14.08ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area133.27 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity112.14 m³·mol⁻¹ChemAxon
Polarizability46.24 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound163012346
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References