Melleolide D (CHEM030668)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:04:14 UTC
Update Date2016-11-09 01:19:07 UTC
Accession NumberCHEM030668
Identification
Common NameMelleolide D
ClassSmall Molecule
DescriptionMelleolide D is found in mushrooms. Melleolide D is from 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 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoic acidHMDB
Chemical FormulaC24H31ClO8
Average Molecular Mass482.951 g/mol
Monoisotopic Mass482.171 g/mol
CAS Registry Number101922-80-9
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 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate
Traditional Name2a,4a,7-trihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,5H,7H,7aH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate
SMILESCOC1=C(Cl)C(C)=C(C(=O)OC2CC3(C)C4C(O)C(C)(C)CC4(O)C=C(CO)C23O)C(O)=C1
InChI IdentifierInChI=1S/C24H31ClO8/c1-11-16(13(27)6-14(32-5)17(11)25)20(29)33-15-8-22(4)18-19(28)21(2,3)10-23(18,30)7-12(9-26)24(15,22)31/h6-7,15,18-19,26-28,30-31H,8-10H2,1-5H3
InChI KeyPSCSRVBGZZBKIW-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
  • O-hydroxybenzoic acid ester
  • P-methoxybenzoic acid or derivatives
  • Methoxyphenol
  • Benzoate ester
  • Salicylic acid or derivatives
  • 3-halobenzoic acid or derivatives
  • Halobenzoic acid or derivatives
  • Benzoic acid or derivatives
  • 4-halophenol
  • Phenoxy compound
  • M-cresol
  • Benzoyl
  • 4-chlorophenol
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Phenol
  • Chlorobenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Halobenzene
  • Toluene
  • Aryl chloride
  • Monocyclic benzene moiety
  • Aryl halide
  • Benzenoid
  • Cyclic alcohol
  • Tertiary alcohol
  • Vinylogous acid
  • Secondary alcohol
  • Carboxylic acid ester
  • Cyclobutanol
  • Carboxylic acid derivative
  • Polyol
  • Monocarboxylic acid or derivatives
  • Ether
  • Organohalogen compound
  • Organic oxygen compound
  • Organochloride
  • Organooxygen compound
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • 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 Solubility0.16 g/LALOGPS
logP1.75ALOGPS
logP2.27ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)9.33ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area136.68 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity121.18 m³·mol⁻¹ChemAxon
Polarizability49.42 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zfr-9770200000-cd835bee892f8eda2fb9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-001i-0009001000-c8f9d1ab528d6db8a5eeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-0120900000-67b73425bc983744ffa9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02h9-0340900000-2cca99ac94de2bbb9fbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-1940000000-767285673ee02b563a8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0110900000-afb66b80873564ba3c33Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0089-0741900000-c52115722c8731e36c35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-9710200000-5c3ed2e46d4e7ffaf436Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0120900000-439a2ebdef09a1b62216Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0440900000-86f39c5b1eab7a3451bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-1950100000-aa58e810811312b20323Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00l2-0240900000-10004e665fb7580c6c5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0950500000-8b1e5523b6b562fe163dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00or-0970200000-6b4f1a4c26c67a1eee62Spectrum
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 IDHMDB0037042
FooDB IDFDB016024
Phenol Explorer IDNot Available
KNApSAcK IDC00021462
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35014357
ChEBI IDNot Available
PubChem Compound ID14166115
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