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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:16:55 UTC
Update Date2022-03-07 02:55:10 UTC
HMDB IDHMDB0037039
Secondary Accession Numbers
  • HMDB37039
Metabolite Identification
Common Name4-O-Methylmelleolide
Description4-O-Methylmelleolide 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. Based on a literature review a small amount of articles have been published on 4-O-Methylmelleolide.
Structure
Data?1563862967
Synonyms
ValueSource
3-Formyl-2a-methoxy-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 FormulaC24H30O6
Average Molecular Weight414.4914
Monoisotopic Molecular Weight414.204238692
IUPAC Name3-formyl-2a-methoxy-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-methoxy-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate
CAS Registry Number96627-13-3
SMILES
COC12C(CC1(C)C1CC(C)(C)CC1C=C2C=O)OC(=O)C1=C(O)C=C(O)C=C1C
InChI Identifier
InChI=1S/C24H30O6/c1-13-6-16(26)8-18(27)20(13)21(28)30-19-11-23(4)17-10-22(2,3)9-14(17)7-15(12-25)24(19,23)29-5/h6-8,12,14,17,19,26-27H,9-11H2,1-5H3
InChI KeyGYCBSZGIYPNYAB-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
  • Resorcinol
  • Benzoyl
  • M-cresol
  • Toluene
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Aldehyde
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point189 - 191 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0098 g/LALOGPS
logP4.17ALOGPS
logP4.75ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)8.7ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity112.8 m³·mol⁻¹ChemAxon
Polarizability45.03 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+193.93231661259
DarkChem[M-H]-192.93431661259
DeepCCS[M-2H]-227.34830932474
DeepCCS[M+Na]+202.85930932474
AllCCS[M+H]+200.432859911
AllCCS[M+H-H2O]+198.132859911
AllCCS[M+NH4]+202.432859911
AllCCS[M+Na]+203.032859911
AllCCS[M-H]-202.532859911
AllCCS[M+Na-2H]-203.032859911
AllCCS[M+HCOO]-203.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-O-MethylmelleolideCOC12C(CC1(C)C1CC(C)(C)CC1C=C2C=O)OC(=O)C1=C(O)C=C(O)C=C1C4322.5Standard polar33892256
4-O-MethylmelleolideCOC12C(CC1(C)C1CC(C)(C)CC1C=C2C=O)OC(=O)C1=C(O)C=C(O)C=C1C2917.0Standard non polar33892256
4-O-MethylmelleolideCOC12C(CC1(C)C1CC(C)(C)CC1C=C2C=O)OC(=O)C1=C(O)C=C(O)C=C1C3156.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-O-Methylmelleolide,1TMS,isomer #1COC12C(C=O)=CC3CC(C)(C)CC3C1(C)CC2OC(=O)C1=C(C)C=C(O)C=C1O[Si](C)(C)C3168.7Semi standard non polar33892256
4-O-Methylmelleolide,1TMS,isomer #2COC12C(C=O)=CC3CC(C)(C)CC3C1(C)CC2OC(=O)C1=C(C)C=C(O[Si](C)(C)C)C=C1O3214.8Semi standard non polar33892256
4-O-Methylmelleolide,2TMS,isomer #1COC12C(C=O)=CC3CC(C)(C)CC3C1(C)CC2OC(=O)C1=C(C)C=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C3212.5Semi standard non polar33892256
4-O-Methylmelleolide,1TBDMS,isomer #1COC12C(C=O)=CC3CC(C)(C)CC3C1(C)CC2OC(=O)C1=C(C)C=C(O)C=C1O[Si](C)(C)C(C)(C)C3374.7Semi standard non polar33892256
4-O-Methylmelleolide,1TBDMS,isomer #2COC12C(C=O)=CC3CC(C)(C)CC3C1(C)CC2OC(=O)C1=C(C)C=C(O[Si](C)(C)C(C)(C)C)C=C1O3427.6Semi standard non polar33892256
4-O-Methylmelleolide,2TBDMS,isomer #1COC12C(C=O)=CC3CC(C)(C)CC3C1(C)CC2OC(=O)C1=C(C)C=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C3598.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-O-Methylmelleolide GC-MS (Non-derivatized) - 70eV, Positivesplash10-01b9-0190000000-fc54f2c8ddb2928de8532017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-O-Methylmelleolide GC-MS (2 TMS) - 70eV, Positivesplash10-01b9-0090010000-b89625ca1e13c6701ead2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-O-Methylmelleolide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-O-Methylmelleolide 10V, Positive-QTOFsplash10-014j-0463900000-ee3787e481ec9177be522015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-O-Methylmelleolide 20V, Positive-QTOFsplash10-0udj-1952100000-08648c12b1ced5038e9b2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-O-Methylmelleolide 40V, Positive-QTOFsplash10-0udi-3910000000-7c4521ac667884a1f0bd2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-O-Methylmelleolide 10V, Negative-QTOFsplash10-03di-0411900000-b7c624f47005d925aece2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-O-Methylmelleolide 20V, Negative-QTOFsplash10-02mj-0963300000-588b1fcb43205abb36d92015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-O-Methylmelleolide 40V, Negative-QTOFsplash10-00xr-2930000000-93ad0db6d2f0a536842f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-O-Methylmelleolide 10V, Positive-QTOFsplash10-014j-0691600000-68afe66fa0857913abc62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-O-Methylmelleolide 20V, Positive-QTOFsplash10-0gb9-4983200000-730bad080449a61e45da2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-O-Methylmelleolide 40V, Positive-QTOFsplash10-0udi-2920000000-1b524fc8a52985ec29b42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-O-Methylmelleolide 10V, Negative-QTOFsplash10-03di-0100900000-a3cfe40000a32d1ece412021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-O-Methylmelleolide 20V, Negative-QTOFsplash10-0229-1923200000-5d1458f192d3b334433f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-O-Methylmelleolide 40V, Negative-QTOFsplash10-00dl-8922000000-b4bda143ebab5d3858962021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB016021
KNApSAcK IDC00021453
Chemspider ID35014355
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound78173000
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.