Melleolide C (CHEM030667)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:04:12 UTC
Update Date2016-11-09 01:19:07 UTC
Accession NumberCHEM030667
Identification
Common NameMelleolide C
ClassSmall Molecule
DescriptionMelleolide C is found in mushrooms. Melleolide C is produced by Armillaria mellea (honey mushroom).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2a,4a,7-Trihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,2ah,4ah,5H,6H,7H,7ah,7BH-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoic acidHMDB
Chemical FormulaC24H32O8
Average Molecular Mass448.506 g/mol
Monoisotopic Mass448.210 g/mol
CAS Registry Number101901-56-8
IUPAC Name2a,4a,7-trihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate
Traditional Name2a,4a,7-trihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,5H,7H,7aH-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate
SMILESCOC1=CC(O)=C(C(=O)OC2CC3(C)C4C(O)C(C)(C)CC4(O)C=C(CO)C23O)C(C)=C1
InChI IdentifierInChI=1S/C24H32O8/c1-12-6-14(31-5)7-15(26)17(12)20(28)32-16-9-22(4)18-19(27)21(2,3)11-23(18,29)8-13(10-25)24(16,22)30/h6-8,16,18-19,25-27,29-30H,9-11H2,1-5H3
InChI KeyXXMVVKDVYBWXPQ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as melleolides and analogues. Melleolides and analogues are compounds with a structure characterized by the presence of a 2-hydroxy-4-methoxy-6-methylbenzoic acid derivative linked to a 3,6,6,7b-tetramethyl-cyclobuta[e]indene moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentMelleolides and analogues
Alternative Parents
Substituents
  • Melleolide-skeleton
  • P-methoxybenzoic acid or derivatives
  • O-hydroxybenzoic acid ester
  • Methoxyphenol
  • Salicylic acid or derivatives
  • Benzoate ester
  • Benzoic acid or derivatives
  • Methoxybenzene
  • Phenoxy compound
  • Benzoyl
  • M-cresol
  • Phenol ether
  • Anisole
  • Toluene
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Tertiary alcohol
  • Cyclic alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Cyclobutanol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Primary alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.34 g/LALOGPS
logP1.11ALOGPS
logP1.67ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)9.76ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area136.68 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity116.38 m³·mol⁻¹ChemAxon
Polarizability47.29 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-9760200000-96003e71c295ae175f21Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-001i-1019000000-a3b6c3d27253769585e7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01qa-0120900000-0a50378a9d067de91824Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03yj-0520900000-1c4e8b518f46ab70d5b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-1950100000-00fe8abda3f717479c96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-0210900000-e9071571988ca905d978Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00mt-0742900000-3d079d6a5459582a3d95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052r-2930000000-91f7c489449577c61c7cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0200900000-d7f52b93756d1b5dcb1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00lj-0941700000-f60d5bcaddce0d92f7a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-7952600000-ff34fbe527edb54d87d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0240900000-c415ba7326f05420a216Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pk-0862900000-0d16a96d8b34f3a2a303Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1901000000-da7af1212fce3c90eca9Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0037041
FooDB IDFDB016023
Phenol Explorer IDNot Available
KNApSAcK IDC00021461
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35014356
ChEBI IDNot Available
PubChem Compound ID14166113
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM