Ergosterol peroxide (CHEM031362)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:35:40 UTC
Update Date2016-11-09 01:19:15 UTC
Accession NumberCHEM031362
Identification
Common NameErgosterol peroxide
ClassSmall Molecule
Descriptionobtained from leaves of Ananas comosus (pineapple). Ergosterol peroxide is found in pineapple and fruits.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-5alpha,8alpha-Epidioxyergosta-6,22-dien-3beta-olHMDB
5a,8a-PeroxyergosterolHMDB
5alpha,8alpha-Epidioxyergosta-6,22-dien-3beta-olHMDB
Ergosterol 5alpha ,8alpha -epidioxideHMDB
Ergosterol endoperoxideHMDB
ERGOSTEROL-5,8-peroxideHMDB
O-(Trifluoromethyl)cinnamic acidHMDB
PeroxyergosterolHMDB
3-Hydroxy-5,7-epidioxyergosta-6,22-dieneMeSH
Ergosterol peroxideMeSH
5,8-Epidioxyergosta-6,22-dien-3-olMeSH
Chemical FormulaC28H44O3
Average Molecular Mass428.647 g/mol
Monoisotopic Mass428.329 g/mol
CAS Registry Number2061-64-5
IUPAC Name5-[(3E)-5,6-dimethylhept-3-en-2-yl]-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-13-ol
Traditional Name5-[(3E)-5,6-dimethylhept-3-en-2-yl]-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-13-ol
SMILESCC(C)C(C)\C=C\C(C)C1CCC2C1(C)CCC1C3(C)CCC(O)CC33OOC21C=C3
InChI IdentifierInChI=1S/C28H44O3/c1-18(2)19(3)7-8-20(4)22-9-10-23-25(22,5)13-12-24-26(6)14-11-21(29)17-27(26)15-16-28(23,24)31-30-27/h7-8,15-16,18-24,29H,9-14,17H2,1-6H3/b8-7+
InChI KeyVXOZCESVZIRHCJ-BQYQJAHWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as ergostane steroids. These are steroids with a structure based on the ergostane skeleton, which arises from the methylation of cholestane at the 24-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassErgostane steroids
Direct ParentErgostane steroids
Alternative Parents
Substituents
  • Ergostane-skeleton
  • Ortho-dioxane
  • Cyclic alcohol
  • Dialkyl peroxide
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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 Solubility2.0e-05 g/LALOGPS
logP6.27ALOGPS
logP6.35ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)15.15ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.69 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity126.82 m³·mol⁻¹ChemAxon
Polarizability51.75 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-4139600000-bf51b0c470350fcc4ce8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0550-6123900000-b90973cd078772a8040cSpectrum
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, Positivesplash10-01t9-2003900000-953a700ae3598966539fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01si-9127300000-48fde4c74b50ad587c31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9211000000-f87e52d049f1289db433Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-b73c27ef3ea74e4f608dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-683bc8b3fbffa21c951aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03xr-2109300000-b697bd4f4f99d7ebd816Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-a509d4af6bebc9e05806Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-05d54a7a2455837a10b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0004900000-a8e48b04e5967d8f9a9dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1004900000-229021979d94041202c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a7i-9024300000-3246138577eb2aa6f147Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9100000000-6daaf016dca71b0948b9Spectrum
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 IDHMDB0037941
FooDB IDFDB017110
Phenol Explorer IDNot Available
KNApSAcK IDC00030200
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkErgosterol peroxide
Chemspider ID4528211
ChEBI IDNot Available
PubChem Compound ID5379713
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Dias DA, Urban S: HPLC and NMR studies of phenoxazone alkaloids from Pycnoporus cinnabarinus. Nat Prod Commun. 2009 Apr;4(4):489-98.
2. Duarte N, Ferreira MJ, Martins M, Viveiros M, Amaral L: Antibacterial activity of ergosterol peroxide against Mycobacterium tuberculosis: dependence upon system and medium employed. Phytother Res. 2007 Jul;21(7):601-4.
3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
4. 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.
5. 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.
6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
7. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
8. The lipid handbook with CD-ROM