Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:04:22 UTC
Update Date2022-03-07 02:55:53 UTC
HMDB IDHMDB0038734
Secondary Accession Numbers
  • HMDB38734
Metabolite Identification
Common NameMacrocarpal E
DescriptionMacrocarpal E belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Based on a literature review a significant number of articles have been published on Macrocarpal E.
Structure
Data?1563863248
SynonymsNot Available
Chemical FormulaC28H40O6
Average Molecular Weight472.6136
Monoisotopic Molecular Weight472.282489012
IUPAC Name2,4,6-trihydroxy-5-{1-[6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-1,2,3,4,6,7,8,8a-octahydronaphthalen-1-yl]-3-methylbutyl}benzene-1,3-dicarbaldehyde
Traditional Name2,4,6-trihydroxy-5-{1-[6-(2-hydroxypropan-2-yl)-4,8a-dimethyl-2,3,4,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylbutyl}benzene-1,3-dicarbaldehyde
CAS Registry NumberNot Available
SMILES
CC(C)CC(C1CCC(C)C2=CC(CCC12C)C(C)(C)O)C1=C(O)C(C=O)=C(O)C(C=O)=C1O
InChI Identifier
InChI=1S/C28H40O6/c1-15(2)11-18(23-25(32)19(13-29)24(31)20(14-30)26(23)33)21-8-7-16(3)22-12-17(27(4,5)34)9-10-28(21,22)6/h12-18,21,31-34H,7-11H2,1-6H3
InChI KeyXJNGQIYBMXBCRU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentEudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
Alternative Parents
Substituents
  • Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
  • Acylphloroglucinol derivative
  • Benzenetriol
  • Hydroxybenzaldehyde
  • Phloroglucinol derivative
  • Benzaldehyde
  • Benzoyl
  • Aryl-aldehyde
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Tertiary alcohol
  • Polyol
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Aldehyde
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP5.16ALOGPS
logP7.92ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)6.69ChemAxon
pKa (Strongest Basic)-0.97ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.06 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity136.09 m³·mol⁻¹ChemAxon
Polarizability52.2 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+206.95931661259
DarkChem[M-H]-203.48731661259
DeepCCS[M-2H]-242.19830932474
DeepCCS[M+Na]+218.70330932474
AllCCS[M+H]+212.932859911
AllCCS[M+H-H2O]+211.032859911
AllCCS[M+NH4]+214.732859911
AllCCS[M+Na]+215.232859911
AllCCS[M-H]-217.532859911
AllCCS[M+Na-2H]-219.232859911
AllCCS[M+HCOO]-221.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Macrocarpal ECC(C)CC(C1CCC(C)C2=CC(CCC12C)C(C)(C)O)C1=C(O)C(C=O)=C(O)C(C=O)=C1O4065.0Standard polar33892256
Macrocarpal ECC(C)CC(C1CCC(C)C2=CC(CCC12C)C(C)(C)O)C1=C(O)C(C=O)=C(O)C(C=O)=C1O3276.1Standard non polar33892256
Macrocarpal ECC(C)CC(C1CCC(C)C2=CC(CCC12C)C(C)(C)O)C1=C(O)C(C=O)=C(O)C(C=O)=C1O3672.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Macrocarpal E,1TMS,isomer #1CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O)C1CCC(C)C2=CC(C(C)(C)O[Si](C)(C)C)CCC21C3615.3Semi standard non polar33892256
Macrocarpal E,1TMS,isomer #2CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C)C1CCC(C)C2=CC(C(C)(C)O)CCC21C3683.1Semi standard non polar33892256
Macrocarpal E,1TMS,isomer #3CC(C)CC(C1=C(O)C(C=O)=C(O[Si](C)(C)C)C(C=O)=C1O)C1CCC(C)C2=CC(C(C)(C)O)CCC21C3681.1Semi standard non polar33892256
Macrocarpal E,2TMS,isomer #1CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C)C1CCC(C)C2=CC(C(C)(C)O[Si](C)(C)C)CCC21C3623.6Semi standard non polar33892256
Macrocarpal E,2TMS,isomer #2CC(C)CC(C1=C(O)C(C=O)=C(O[Si](C)(C)C)C(C=O)=C1O)C1CCC(C)C2=CC(C(C)(C)O[Si](C)(C)C)CCC21C3620.2Semi standard non polar33892256
Macrocarpal E,2TMS,isomer #3CC(C)CC(C1=C(O[Si](C)(C)C)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C)C1CCC(C)C2=CC(C(C)(C)O)CCC21C3717.0Semi standard non polar33892256
Macrocarpal E,2TMS,isomer #4CC(C)CC(C1=C(O)C(C=O)=C(O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C)C1CCC(C)C2=CC(C(C)(C)O)CCC21C3719.5Semi standard non polar33892256
Macrocarpal E,3TMS,isomer #1CC(C)CC(C1=C(O[Si](C)(C)C)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C)C1CCC(C)C2=CC(C(C)(C)O[Si](C)(C)C)CCC21C3644.3Semi standard non polar33892256
Macrocarpal E,3TMS,isomer #2CC(C)CC(C1=C(O)C(C=O)=C(O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C)C1CCC(C)C2=CC(C(C)(C)O[Si](C)(C)C)CCC21C3643.1Semi standard non polar33892256
Macrocarpal E,3TMS,isomer #3CC(C)CC(C1=C(O[Si](C)(C)C)C(C=O)=C(O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C)C1CCC(C)C2=CC(C(C)(C)O)CCC21C3732.0Semi standard non polar33892256
Macrocarpal E,4TMS,isomer #1CC(C)CC(C1=C(O[Si](C)(C)C)C(C=O)=C(O[Si](C)(C)C)C(C=O)=C1O[Si](C)(C)C)C1CCC(C)C2=CC(C(C)(C)O[Si](C)(C)C)CCC21C3672.6Semi standard non polar33892256
Macrocarpal E,1TBDMS,isomer #1CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O)C1CCC(C)C2=CC(C(C)(C)O[Si](C)(C)C(C)(C)C)CCC21C3848.1Semi standard non polar33892256
Macrocarpal E,1TBDMS,isomer #2CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C(C)(C)C)C1CCC(C)C2=CC(C(C)(C)O)CCC21C3917.3Semi standard non polar33892256
Macrocarpal E,1TBDMS,isomer #3CC(C)CC(C1=C(O)C(C=O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C1O)C1CCC(C)C2=CC(C(C)(C)O)CCC21C3921.2Semi standard non polar33892256
Macrocarpal E,2TBDMS,isomer #1CC(C)CC(C1=C(O)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C(C)(C)C)C1CCC(C)C2=CC(C(C)(C)O[Si](C)(C)C(C)(C)C)CCC21C4114.9Semi standard non polar33892256
Macrocarpal E,2TBDMS,isomer #2CC(C)CC(C1=C(O)C(C=O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C1O)C1CCC(C)C2=CC(C(C)(C)O[Si](C)(C)C(C)(C)C)CCC21C4124.6Semi standard non polar33892256
Macrocarpal E,2TBDMS,isomer #3CC(C)CC(C1=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C(C)(C)C)C1CCC(C)C2=CC(C(C)(C)O)CCC21C4175.8Semi standard non polar33892256
Macrocarpal E,2TBDMS,isomer #4CC(C)CC(C1=C(O)C(C=O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C1O[Si](C)(C)C(C)(C)C)C1CCC(C)C2=CC(C(C)(C)O)CCC21C4189.4Semi standard non polar33892256
Macrocarpal E,3TBDMS,isomer #1CC(C)CC(C1=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C(O)C(C=O)=C1O[Si](C)(C)C(C)(C)C)C1CCC(C)C2=CC(C(C)(C)O[Si](C)(C)C(C)(C)C)CCC21C4321.1Semi standard non polar33892256
Macrocarpal E,3TBDMS,isomer #2CC(C)CC(C1=C(O)C(C=O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C1O[Si](C)(C)C(C)(C)C)C1CCC(C)C2=CC(C(C)(C)O[Si](C)(C)C(C)(C)C)CCC21C4332.9Semi standard non polar33892256
Macrocarpal E,3TBDMS,isomer #3CC(C)CC(C1=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C(O[Si](C)(C)C(C)(C)C)C(C=O)=C1O[Si](C)(C)C(C)(C)C)C1CCC(C)C2=CC(C(C)(C)O)CCC21C4379.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Macrocarpal E GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-7043900000-22e3e56bcf2b5e0a0d7a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Macrocarpal E GC-MS (3 TMS) - 70eV, Positivesplash10-00e9-3112019000-6365d73b9406f855e6d72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Macrocarpal E GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Macrocarpal E 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 - Macrocarpal E 10V, Positive-QTOFsplash10-0ab9-0010900000-c6ba33365147f4db75092016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macrocarpal E 20V, Positive-QTOFsplash10-0a4i-2043900000-d06f43b9833fdfe2263d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macrocarpal E 40V, Positive-QTOFsplash10-0pi9-4069300000-ab132233e0d75c6300632016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macrocarpal E 10V, Negative-QTOFsplash10-00di-0000900000-18b45f07fb54edca02c32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macrocarpal E 20V, Negative-QTOFsplash10-0h9r-0210900000-5a56917b2782d8fa7c232016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macrocarpal E 40V, Negative-QTOFsplash10-01rx-5976600000-a80618b6bb3702ae2a392016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macrocarpal E 10V, Positive-QTOFsplash10-05fs-1043900000-104f6ee8bfc3f70123f72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macrocarpal E 20V, Positive-QTOFsplash10-0fmi-0393300000-a7d554e51f16f15bc42a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macrocarpal E 40V, Positive-QTOFsplash10-0006-2900000000-2942b08a1653070f64bf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macrocarpal E 10V, Negative-QTOFsplash10-00di-0000900000-025afde3cd0f171664392021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macrocarpal E 20V, Negative-QTOFsplash10-0kmi-3610900000-8898b0edb926ff81c21b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Macrocarpal E 40V, Negative-QTOFsplash10-0fef-6936300000-a84d99c7a61ede554ad32021-09-24Wishart 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 IDFDB018145
KNApSAcK IDNot Available
Chemspider ID400196
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound454461
PDB IDNot Available
ChEBI ID175708
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.