10-Hydroxymelleolide (CHEM032131)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:09:51 UTC
Update Date2016-11-09 01:19:24 UTC
Accession NumberCHEM032131
Identification
Common Name10-Hydroxymelleolide
ClassSmall Molecule
Description10-Hydroxymelleolide is found in mushrooms. 10-Hydroxymelleolide is a metabolite of Armillariella mellea (honey mushroom).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Formyl-2a,7-dihydroxy-6,6,7b-trimethyl-1H,2H,2ah,4ah,5H,6H,7H,7ah,7BH-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoic acidHMDB
Chemical FormulaC23H28O7
Average Molecular Mass416.464 g/mol
Monoisotopic Mass416.184 g/mol
CAS Registry Number130396-93-9
IUPAC Name3-formyl-2a,7-dihydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate
Traditional Name3-formyl-2a,7-dihydroxy-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate
SMILESCC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3C(CC(C)(C)C3O)C=C(C=O)C12O
InChI IdentifierInChI=1S/C23H28O7/c1-11-5-14(25)7-15(26)17(11)20(28)30-16-9-22(4)18-12(8-21(2,3)19(18)27)6-13(10-24)23(16,22)29/h5-7,10,12,16,18-19,25-27,29H,8-9H2,1-4H3
InChI KeyVNRLQDGXGABKPC-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-hydroxybenzoic acid alkyl ester
  • P-hydroxybenzoic acid ester
  • O-hydroxybenzoic acid ester
  • Dihydroxybenzoic acid
  • Salicylic acid or derivatives
  • Benzoate ester
  • Benzoic acid or derivatives
  • Benzoyl
  • Resorcinol
  • M-cresol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Toluene
  • Benzenoid
  • Monocyclic benzene moiety
  • Cyclic alcohol
  • Vinylogous acid
  • Tertiary alcohol
  • Cyclobutanol
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Aldehyde
  • 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 Solubility0.19 g/LALOGPS
logP2.14ALOGPS
logP2.95ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)8.7ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.29 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.49 m³·mol⁻¹ChemAxon
Polarizability43.47 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, Positivesplash10-0fk9-2960000000-a55e0b673b9fc656d7f0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0173-4092024000-33b8e24df1dad5de19b0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0459500000-c57d27f054bceaa1c8a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uea-0946100000-aa98a13cb21fdf5dfabfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-2920000000-e420810c00bd82ab6984Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0513900000-f7c9250df700f4651efcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ba-0953300000-239dc5d7c9de79cfff65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-2920000000-f1889b64cc0c34bf30caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0694800000-00bc539da78835eb40deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uea-3942100000-dc2c6a2ecc0e00c774e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-5911000000-5190b6bc616877ab0dbdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0200900000-7eb14eef3a94a47c0031Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-1943100000-ffee4917d62f73acfcb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-8912000000-40434837d3a405efa41bSpectrum
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 IDHMDB0038786
FooDB IDFDB018208
Phenol Explorer IDNot Available
KNApSAcK IDC00021456
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35014660
ChEBI ID175331
PubChem Compound ID14707328
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