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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:02:30 UTC
Update Date2019-07-23 06:27:23 UTC
HMDB IDHMDB0038705
Secondary Accession Numbers
  • HMDB38705
Metabolite Identification
Common NameMacrocarpal C
DescriptionMacrocarpal C belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. Macrocarpal C is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563863243
SynonymsNot Available
Chemical FormulaC28H38O5
Average Molecular Weight454.5983
Monoisotopic Molecular Weight454.271924326
IUPAC Name2,4,6-trihydroxy-5-(3-methyl-1-{1,1,2-trimethyl-5-methylidene-decahydro-1H-cyclopropa[e]azulen-2-yl}butyl)benzene-1,3-dicarbaldehyde
Traditional Name2,4,6-trihydroxy-5-(3-methyl-1-{1,1,2-trimethyl-5-methylidene-octahydrocyclopropa[e]azulen-2-yl}butyl)benzene-1,3-dicarbaldehyde
CAS Registry Number142628-53-3
SMILES
CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O)C1(C)CCC2C1C1C(CCC2=C)C1(C)C
InChI Identifier
InChI=1S/C28H38O5/c1-14(2)11-20(21-25(32)17(12-29)24(31)18(13-30)26(21)33)28(6)10-9-16-15(3)7-8-19-23(22(16)28)27(19,4)5/h12-14,16,19-20,22-23,31-33H,3,7-11H2,1-2,4-6H3
InChI KeyIEWHEHWXBLPFER-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct Parent5,10-cycloaromadendrane sesquiterpenoids
Alternative Parents
Substituents
  • Guaiane sesquiterpenoid
  • 5,10-cycloaromadendrane sesquiterpenoid
  • Acylphloroglucinol derivative
  • Benzenetriol
  • Phloroglucinol derivative
  • Hydroxybenzaldehyde
  • Benzoyl
  • Benzaldehyde
  • Aryl-aldehyde
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Polyol
  • Hydrocarbon derivative
  • Aldehyde
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • 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 Solubility0.018 g/LALOGPS
logP4.79ALOGPS
logP8.6ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)6.68ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity131.28 m³·mol⁻¹ChemAxon
Polarizability50.26 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ug1-6375900000-006a73eb3d14afae17d6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0bt9-3110409000-9ccf1e9e633f5cb41715Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0010900000-908d5a0dcd19539f2c15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-4251900000-a5eb9e770193cd3640f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-7793600000-34a5bac00d12c03891e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-35d083ee7055b176839dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0310900000-11f6e5b006e4a0f86d15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dr-6987500000-f3ba2a52f76bbf5df39aSpectrum
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 IDFDB018112
KNApSAcK IDNot Available
Chemspider ID8271035
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10095499
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.