Melleolide H (CHEM032133)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:09:57 UTC
Update Date2016-11-09 01:19:24 UTC
Accession NumberCHEM032133
Identification
Common NameMelleolide H
ClassSmall Molecule
DescriptionMelleolide H is found in mushrooms. Melleolide H is a metabolite of Armillariella mellea (honey mushroom).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
ArmillariginHMDB
3-Formyl-2a,7-dihydroxy-6,6,7b-trimethyl-1H,2H,2ah,4ah,5H,6H,7H,7ah,7BH-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoic acidGenerator
Chemical FormulaC24H30O7
Average Molecular Mass430.491 g/mol
Monoisotopic Mass430.199 g/mol
CAS Registry Number117240-47-8
IUPAC Name3-formyl-2a,7-dihydroxy-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 Name3-formyl-2a,7-dihydroxy-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 2-hydroxy-4-methoxy-6-methylbenzoate
SMILESCOC1=CC(O)=C(C(=O)OC2CC3(C)C4C(CC(C)(C)C4O)C=C(C=O)C23O)C(C)=C1
InChI IdentifierInChI=1S/C24H30O7/c1-12-6-15(30-5)8-16(26)18(12)21(28)31-17-10-23(4)19-13(9-22(2,3)20(19)27)7-14(11-25)24(17,23)29/h6-8,11,13,17,19-20,26-27,29H,9-10H2,1-5H3
InChI KeyNQAHWJIWYRYXFP-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
  • Salicylic acid or derivatives
  • Benzoate ester
  • Methoxyphenol
  • Benzoic acid or derivatives
  • Benzoyl
  • Methoxybenzene
  • M-cresol
  • Phenol ether
  • Phenoxy compound
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • Toluene
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Cyclic alcohol
  • Tertiary alcohol
  • Cyclobutanol
  • Carboxylic acid ester
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aldehyde
  • Carbonyl group
  • Organic oxygen compound
  • 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 Solubility0.072 g/LALOGPS
logP2.32ALOGPS
logP3.1ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)9.76ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity113.97 m³·mol⁻¹ChemAxon
Polarizability45.69 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, Positivesplash10-00y0-2970100000-d3c9542f6fee0bdc3965Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0gb9-2009001000-dfb31a531681026ddfe1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0231900000-8045dcf8ae682dc18e19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0943400000-bf80a17f287c9562c005Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-1920000000-9d66ac09c845f7634415Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0310900000-b9eecca36b48619f3da7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ri-0951600000-c6a1c08debdc27e672fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-2920000000-6633bb34106bb228e05aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0210900000-bf64bbf480d5a2c0a6b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0967300000-65f5055e4daca693b8ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-6759200000-32ecef1d64d1f8f1e48aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0371900000-1dfbffad2e4dce44496cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02ar-2963400000-80c58885bd5f51df56f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-2910000000-e2c88da4bbc9bcbccbaaSpectrum
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 IDHMDB0038788
FooDB IDFDB018210
Phenol Explorer IDNot Available
KNApSAcK IDC00054140
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35014662
ChEBI ID175488
PubChem Compound ID14166122
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