(3beta,5alpha,9alpha,22E,24R)-3,5,9-Trihydroxy-23-methylergosta-7,22-dien-6-one (CHEM027009)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 23:26:18 UTC
Update Date2016-11-09 01:18:22 UTC
Accession NumberCHEM027009
Identification
Common Name(3beta,5alpha,9alpha,22E,24R)-3,5,9-Trihydroxy-23-methylergosta-7,22-dien-6-one
ClassSmall Molecule
DescriptionConstituent of Lentinus edodes (shiitake). (3beta,5alpha,9alpha,22E,24R)-3,5,9-Trihydroxy-23-methylergosta-7,22-dien-6-one is found in mushrooms.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3b,5a,9a,22E,24R)-3,5,9-Trihydroxy-23-methylergosta-7,22-dien-6-oneGenerator
(3Β,5α,9α,22E,24R)-3,5,9-trihydroxy-23-methylergosta-7,22-dien-6-oneGenerator
11-Amino-undecanoic acidHMDB
11-Aminoundecanoic acidHMDB
11-Aminoundecanoic acid homopolymerHMDB
11-Aminoundecyclic acidHMDB
11-Aminoundecylic acidHMDB
Aminoundecanoic acidHMDB
Nylon 11HMDB
Nylon-11HMDB
Omega-aminoundecanoic acidHMDB
Poly(imino(1-oxo-1,11-undecanediyl))HMDB
PolyundecanolactamHMDB
Undecanoic acid, 11-amino-, homopolymerHMDB
Undecanoic acid, 11-amino-, polyamideHMDB
Chemical FormulaC29H46O4
Average Molecular Mass458.673 g/mol
Monoisotopic Mass458.340 g/mol
CAS Registry Number211486-12-3
IUPAC Name1,5,7-trihydroxy-2,15-dimethyl-14-[(3E)-4,5,6-trimethylhept-3-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-8-one
Traditional Name1,5,7-trihydroxy-2,15-dimethyl-14-[(3E)-4,5,6-trimethylhept-3-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-8-one
SMILESCC(C)C(C)C(\C)=C\C(C)C1CCC2C3=CC(=O)C4(O)CC(O)CCC4(C)C3(O)CCC12C
InChI IdentifierInChI=1S/C29H46O4/c1-17(2)20(5)18(3)14-19(4)22-8-9-23-24-15-25(31)29(33)16-21(30)10-11-27(29,7)28(24,32)13-12-26(22,23)6/h14-15,17,19-23,30,32-33H,8-13,16H2,1-7H3/b18-14+
InChI KeyMRERMGPPCLQIPD-NBVRZTHBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassErgostane steroids
Direct ParentErgosterols and derivatives
Alternative Parents
Substituents
  • Ergosterol-skeleton
  • 3-hydroxy-delta-7-steroid
  • 3-hydroxysteroid
  • 6-oxosteroid
  • 5-hydroxysteroid
  • Hydroxysteroid
  • Oxosteroid
  • Delta-7-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Tertiary alcohol
  • Secondary alcohol
  • Ketone
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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 Solubility0.0052 g/LALOGPS
logP4.29ALOGPS
logP4.89ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)12.48ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity133.94 m³·mol⁻¹ChemAxon
Polarizability53.07 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004u-1224900000-b9686b2b0d87ab13ef2eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0bt9-2100019000-5a65a6ae42274e50ea4bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-1001900000-3194c073be8f211ecae8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006y-7224900000-4dead09fd49eeb75e65cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9342200000-7896973f603352a54ce2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-4bd8b9788b45d596685cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0300900000-c9965c488acce9986f63Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-5208900000-0364577404f7fe9c8a12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-442f12536d077727e77cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-83915f13d4b33be52267Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4u-0005900000-a94595a991c49e9dcc02Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-4003900000-72afaeb734df37bc9030Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-9105400000-b350c41612050d8e85c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-9211000000-b160e219bf88b6313d8cSpectrum
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 IDHMDB0032669
FooDB IDFDB010622
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID131751277
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM