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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:04:17 UTC
Update Date2019-07-23 06:27:28 UTC
HMDB IDHMDB0038733
Secondary Accession Numbers
  • HMDB38733
Metabolite Identification
Common NameMacrocarpal D
DescriptionMacrocarpal D is a constituent of Eucalyptus globulus (Tasmanian blue gum).
Structure
Data?1563863248
SynonymsNot Available
Chemical FormulaC28H40O6
Average Molecular Weight472.6136
Monoisotopic Molecular Weight472.282489012
IUPAC Name2,4,6-trihydroxy-5-{1-[7-(2-hydroxypropan-2-yl)-1,4-dimethyl-1,2,3,3a,4,5,6,7-octahydroazulen-1-yl]-3-methylbutyl}benzene-1,3-dicarbaldehyde
Traditional Name2,4,6-trihydroxy-5-{1-[7-(2-hydroxypropan-2-yl)-1,4-dimethyl-3,3a,4,5,6,7-hexahydro-2H-azulen-1-yl]-3-methylbutyl}benzene-1,3-dicarbaldehyde
CAS Registry NumberNot Available
SMILES
CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O)C1(C)CCC2C(C)CCC(C=C12)C(C)(C)O
InChI Identifier
InChI=1S/C28H40O6/c1-15(2)11-22(23-25(32)19(13-29)24(31)20(14-30)26(23)33)28(6)10-9-18-16(3)7-8-17(12-21(18)28)27(4,5)34/h12-18,22,31-34H,7-11H2,1-6H3
InChI KeyVUKIJLQDSQXHDI-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentGuaianes
Alternative Parents
Substituents
  • Guaiane sesquiterpenoid
  • Acylphloroglucinol derivative
  • Hydroxybenzaldehyde
  • Phloroglucinol derivative
  • Benzenetriol
  • Benzoyl
  • Benzaldehyde
  • Aryl-aldehyde
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Tertiary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP5.17ALOGPS
logP7.92ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)6.66ChemAxon
pKa (Strongest Basic)-0.96ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.06 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity136.09 m³·mol⁻¹ChemAxon
Polarizability52.6 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9152800000-ab27f81658a2200c15e1JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0avi-7010509000-222b767260e28a385ec6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0010900000-1813bd7798a806e6ff41JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-0021900000-676d5ce4c0a43432f999JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2369400000-5ac9e6cfef3e6e41b3e8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-249d7a3d022c45bd3bfeJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0h9r-0310900000-e6ed301f842ed53e71a2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-008c-2191100000-2c46c4f588ba67ff28abJSpectraViewer | MoNA
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
FoodDB IDFDB018144
KNApSAcK IDNot Available
Chemspider ID400195
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound454460
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH 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.