7,8-Didehydrodesmosterol (YMDB01489)

Identification
YMDB IDYMDB01489
Name7,8-Didehydrodesmosterol
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description7-Dehydrodesmosterol, also known as 24-dehydroprovitamin D3, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 7-dehydrodesmosterol is considered to be a sterol. Based on a literature review a significant number of articles have been published on 7-Dehydrodesmosterol.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 24-Dehydroprovitamin D3
  • 7-dehydrodesmosterol
  • Cholesta-5,7,24-trien-3-ol, (3beta)-
  • Cholesta-5,7,24-trien-3beta-ol
  • Cholesta-5,7,24-triene-3beta-ol
  • Cholesta-5,7,24-trien-3b-ol
  • Cholesta-5,7,24-trien-3β-ol
  • Cholesta-5,7,24-triene-3b-ol
  • Cholesta-5,7,24-triene-3β-ol
  • Cholesta-5,7,24-trien-3 beta-ol
CAS number1715-86-2
WeightAverage: 382.6218
Monoisotopic: 382.323565966
InChI KeyRUSSPKPUXDSHNC-UHFFFAOYSA-N
InChIInChI=1S/C27H42O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,9-10,19,21,23-25,28H,6,8,11-17H2,1-5H3
IUPAC Name(1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol
Traditional IUPAC Name(1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol
Chemical FormulaC27H42O
SMILESCC(CCC=C(C)C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C
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
  • Cholesterol-skeleton
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxy-delta-7-steroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • Delta-7-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogP6.101PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00064 g/LALOGPS
logP7.46ALOGPS
logP6.3ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)18.27ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity122.32 m³·mol⁻¹ChemAxon
Polarizability48.87 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Cholesterol biosynthesis and metabolism CE(10:0)PW002545 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(12:0)PW002548 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(14:0)PW002544 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(16:0)PW002550 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(18:0)PW002551 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Steroid biosynthesisec00100 Map00100
SMPDB Reactions
7,8-Didehydrodesmosterol + NADPH ↔ 7-Dehydrocholesterol + NADP
5a-cholesta-7,24-dien-3B-ol → 7,8-Didehydrodesmosterol
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, Positivesplash10-0gi0-1019000000-873a0675c614937f5167JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-009l-3005900000-0215415f55ca045c8a21JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0019000000-efc1163570a7981b4304JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-067i-3149000000-7066d7865c8679b6ce89JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4349000000-c831059d6c69b04010e5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-3be597719610dcae03e8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-2a8728016430bb3e3dd8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014j-1019000000-aa1ecf0c3ee0da1fc01eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-334e990fc728bf944c79JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-a497ed6306144dc39405JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0009000000-13938bbaae8b6325524cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0029000000-8e9727bf1d7dd88dd659JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zgi-5089000000-c68d3deb786943f988d6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-9830000000-1416c39d793c0b990a13JSpectraViewer
References
References:
  • Yannai S. Dictionary of food compounds with CD-ROM: additives, flavors, and ingredients. Chapman & Hall/CRC; 2004.
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID27910
HMDB IDHMDB03896
Pubchem Compound ID440558
Kegg IDC05107
ChemSpider ID4292297
FOODB IDFDB012781
Wikipedia ID7-Dehydrodesmosterol
BioCyc IDCPD-8646

Enzymes

Protein Details
1. C-5 sterol desaturase
General function:
Involved in iron ion binding
Specific function:
Catalyzes the introduction of a C-5 double bond in the B ring of ergosterol. May contribute to the regulation of ergosterol biosynthesis
Gene Name:
ERG3
Uniprot ID:
P32353
Molecular weight:
42729.89844
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