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Record Information
Version2.0
Created at2022-04-28 04:07:30 UTC
Updated at2022-04-28 04:07:30 UTC
NP-MRD IDNP0058779
Secondary Accession NumbersNone
Natural Product Identification
Common NameIxerin G
Description(2R,3R,4S,5S,6S)-2-{[(3aS,11aS)-6-formyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-yl]methoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 2-(4-hydroxyphenyl)acetate 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. Ixerin G is found in Ixeris tamagawaensis. Based on a literature review very few articles have been published on (2R,3R,4S,5S,6S)-2-{[(3aS,11aS)-6-formyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-yl]methoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 2-(4-hydroxyphenyl)acetate.
Structure
Thumb
Synonyms
ValueSource
(2R,3R,4S,5S,6S)-2-{[(3as,11as)-6-formyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-10-yl]methoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 2-(4-hydroxyphenyl)acetic acidGenerator
Chemical FormulaC29H34O11
Average Mass558.5800 Da
Monoisotopic Mass558.21011 Da
IUPAC Name(2R,3R,4S,5S,6S)-2-{[(3aS,11aS)-6-formyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-yl]methoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl 2-(4-hydroxyphenyl)acetate
Traditional Name(2R,3R,4S,5S,6S)-2-{[(3aS,11aS)-6-formyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-10-yl]methoxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (4-hydroxyphenyl)acetate
CAS Registry NumberNot Available
SMILES
OC[C@@H]1O[C@@H](OC\C2=C\[C@@H]3OC(=O)C(=C)[C@@H]3CC\C(C=O)=C/CC2)[C@H](OC(=O)CC2=CC=C(O)C=C2)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C29H34O11/c1-16-21-10-7-18(13-30)3-2-4-19(11-22(21)38-28(16)36)15-37-29-27(26(35)25(34)23(14-31)39-29)40-24(33)12-17-5-8-20(32)9-6-17/h3,5-6,8-9,11,13,21-23,25-27,29,31-32,34-35H,1-2,4,7,10,12,14-15H2/b18-3+,19-11+/t21-,22-,23-,25+,26-,27+,29+/m0/s1
InChI KeyHSJGWYWRALHJJB-IPTZCKKGSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ixeris tamagawaensisPlant
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentGermacranolides and derivatives
Alternative Parents
Substituents
  • Terpene glycoside
  • Germacranolide
  • Sesquiterpenoid
  • Germacrane sesquiterpenoid
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Gamma butyrolactone
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Acetal
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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
logP1.57ALOGPS
logP1.77ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)9.5ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area169.05 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity140.78 m³·mol⁻¹ChemAxon
Polarizability56.24 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
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 Compound162971626
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available