4a-Methylzymosterol (CHEM035126)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:30:36 UTC
Update Date2016-11-09 01:21:15 UTC
Accession NumberCHEM035126
Identification
Common Name4a-Methylzymosterol
ClassSmall Molecule
DescriptionA 3beta-sterol that is zymosterol substituted by a 4alpha-methyl group.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3beta,4alpha,5alpha)-4-Methylcholesta-8,24-dien-3-olChEBI
4alpha-Methyl-5alpha-cholesta-8,24-dien-3beta-olChEBI
(3b,4a,5a)-4-Methylcholesta-8,24-dien-3-olGenerator
(3β,4α,5α)-4-Methylcholesta-8,24-dien-3-olGenerator
4a-Methyl-5a-cholesta-8,24-dien-3b-olGenerator
4α-Methyl-5α-cholesta-8,24-dien-3β-olGenerator
(4S,5S)-4,10,13-Trimethyl-17-(6-methylhept-5-en-2-yl)-2,3,4,5,6,7,11,12,14, 15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-olHMDB
4alpha-MethylzymosterolHMDB
4alpha-Methyl-5alpha-cholesta-8(9),24-dien-3beta-olHMDB
4alpha-Methyl-delta8,24-cholestenolHMDB
4α-Methyl-5α-cholesta-8(9),24-dien-3β-olHMDB
4α-Methyl-Δ8,24-cholestenolHMDB
4α-MethylzymosterolHMDB
Chemical FormulaC28H46O
Average Molecular Mass398.664 g/mol
Monoisotopic Mass398.355 g/mol
CAS Registry Number7448-03-5
IUPAC Name(2S,5S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
Traditional Name(2S,5S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
SMILES[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C
InChI IdentifierInChI=1S/C28H46O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h8,19-20,22-24,26,29H,7,9-17H2,1-6H3/t19-,20+,22-,23+,24+,26+,27-,28+/m1/s1
InChI KeyFOUJWBXBKVVHCJ-YIJYGBTNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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 Solubility0.0007 g/LALOGPS
logP6.52ALOGPS
logP7.03ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)18.96ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity125.67 m³·mol⁻¹ChemAxon
Polarizability51.73 ųChemAxon
Number of Rings4ChemAxon
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, Positivesplash10-02ar-0019000000-da364020d6f55a8d1836Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4l-3004900000-86ae2efd8b737e675270Spectrum
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, Positivesplash10-001j-0009000000-f485cbb263f2f4b1b84aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01sj-2129000000-22c00d60920d1e5a4fabSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-3459000000-7d25553141c326b6521eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-da18f5394671385950baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-dbaa936472d9a3662d91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0159-1009000000-dcd434b2beb43e39f10bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-0ca06bc1a59e9690d939Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-0ca06bc1a59e9690d939Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0009000000-4d79474ae6f15f5ccfe9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0019000000-7f62fafcf8fff91b75e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066r-7279000000-1d2e823ffd821f5bcb5eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-8940000000-81f109206bc11ddf7c5dSpectrum
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 IDHMDB0001217
FooDB IDFDB022496
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc ID4-METHYL-824-CHOLESTADIENOL
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID20036827
ChEBI ID1949
PubChem Compound ID5280360
Kegg Compound IDC05103
YMDB IDYMDB00611
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1154452
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1449509
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=356938
4. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19.