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Delta 8,14 -Sterol (YMDB00015)

Identification
YMDB IDYMDB00015
NameDelta 8,14 -Sterol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionDelta 8,14 -Sterol, also known as δ8,14 -sterol, 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. Thus, Delta 8,14 -sterol is considered to be a sterol lipid molecule. Delta 8,14 -Sterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 4-alpha-methyl-5-alpha-ergosta-8,14,24(28)-trien-3-beta-ol
  • 4a-Methyl-5a-ergosta-8,14,24(28)-trien-3b-ol
  • 4a-Methylergosta-8,14,24(241)-trien-3b-ol
  • 4alpha-Methyl-5alpha-ergosta-8,14,24(28)-trien-3beta-ol
  • delta 8,14 -Sterol
  • delta8,14 -Sterol
  • delta8,14-Sterol
  • δ 8,14 -sterol
  • δ8,14 -sterol
  • δ8,14-sterol
  • (3beta,4alpha,5alpha)-4-Methylergosta-8,14,24(28)-trien-3-ol
  • (3β,4α,5α)-4-Methylergosta-8,14,24(28)-trien-3-ol
  • 4alpha-Methylergosta-8,14,24(241)-trien-3beta-ol
  • 4α-Methyl-5α-ergosta-8,14,24(28)-trien-3β-ol
  • 4α-Methylergosta-8,14,24(241)-trien-3β-ol
CAS number74635-33-9
WeightAverage: 410.6749
Monoisotopic: 410.354866094
InChI KeyHLAWVOWADPNAGN-BAHZUFOISA-N
InChIInChI=1S/C29H46O/c1-18(2)19(3)8-9-20(4)23-12-13-25-22-10-11-24-21(5)27(30)15-17-29(24,7)26(22)14-16-28(23,25)6/h13,18,20-21,23-24,27,30H,3,8-12,14-17H2,1-2,4-7H3/t20-,21+,23-,24+,27+,28-,29+/m1/s1
IUPAC Name(2S,5S,6S,7S,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-5-ol
Traditional IUPAC Name(2S,5S,6S,7S,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-5-ol
Chemical FormulaC29H46O
SMILES[H]O[C@@]1([H])C([H])([H])C([H])([H])[C@@]2(C3=C(C4=C([H])C([H])([H])[C@]([H])([C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C(=C([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H])[C@@]4(C([H])([H])[H])C([H])([H])C3([H])[H])C([H])([H])C([H])([H])[C@@]2([H])[C@]1([H])C([H])([H])[H])C([H])([H])[H]
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-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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0016 g/LALOGPS
logP7ALOGPS
logP6.97ChemAxon
logS-5.4ALOGPS
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 Count5ChemAxon
Refractivity130 m³·mol⁻¹ChemAxon
Polarizability53.06 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cellular membrane
Organoleptic PropertiesNot Available
SMPDB Pathways
Steroid biosynthesisPW002482 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Steroid biosynthesisec00100 Map00100
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-0009000000-3be06a7a2e1d781b5fa8JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0gb9-2003900000-1ddc0b2fd8c5c5050903JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-1019500000-046d99a719521520a221JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053u-5239100000-35e12a7ac241ea6b3d5eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05o0-7179000000-157b7d71a0b50a4f6cfaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0002900000-3112227426dc5f73b598JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0004900000-6302f767a4949cfeabe0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-2009000000-1068ac4ee572fe372b16JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02t9-0079400000-909cacfa5264a8b97053JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-5295000000-8fdfbe980fb078069131JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014u-9431000000-dd7d0e22284f4ddcce4cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-84eae2c8ad8ccafd7741JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-bf8e63a2888265bea2deJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0001900000-7b92331f9804da3440edJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID30109
HMDB IDHMDB06928
Pubchem Compound ID443237
Kegg IDC11508
ChemSpider ID24676912
FOODB IDFDB011216
Wikipedia IDNot Available
BioCyc IDCPD-9523

Enzymes

Protein Details
1. Lanosterol 14-alpha demethylase
General function:
Involved in iron ion binding
Specific function:
Catalyzes C14-demethylation of lanosterol which is critical for ergosterol biosynthesis. It transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol
Gene Name:
ERG11
Uniprot ID:
P10614
Molecular weight:
60719.80078
Reactions
Obtusifoliol + 3 O(2) + 3 NADPH → 4-alpha-methyl-5-alpha-ergosta-8,14,24(28)-trien-3-beta-ol + formate + 3 NADP(+) + 4 H(2)O.