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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-13 11:32:19 UTC
Update Date2021-09-14 15:19:01 UTC
HMDB IDHMDB0006842
Secondary Accession Numbers
  • HMDB0000997
  • HMDB00997
  • HMDB06842
Metabolite Identification
Common Name5alpha-Cholesta-7,24-dien-3beta-ol
Description5alpha-Cholesta-7,24-dien-3beta-ol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 5alpha-cholesta-7,24-dien-3beta-ol is considered to be a sterol lipid molecule. 5alpha-Cholesta-7,24-dien-3beta-ol is involved in the biosynthesis of steroids. 5alpha-Cholesta-7,24-dien-3beta-ol is reversibly converted into 5alpha-cholest-7-en-3beta-ol by delta24-sterol reductase (EC 1.3.1.72). 5alpha-Cholesta-7,24-dien-3beta-ol is also converted into zymosterol by cholestenol delta-isomerase (EC 5.3.3.5). 5alpha-Cholesta-7,24-dien-3beta-ol is also converted into 7-Dehydrodesmosterol. 5alpha-Cholesta-7,24-dien-3beta-ol is a substrate for 3-beta-hydroxysteroid-delta(8),delta(7)-isomerase.
Structure
Data?1595282014
Synonyms
ValueSource
(3beta,5alpha)-Cholesta-7,24-dien-3-olChEBI
Cholesta-7,24-dien-3-olChEBI
(3b,5a)-Cholesta-7,24-dien-3-olGenerator
(3β,5α)-Cholesta-7,24-dien-3-olGenerator
5a-Cholesta-7,24-dien-3b-olGenerator
5α-Cholesta-7,24-dien-3β-olGenerator
5 alpha-Cholesta-7,24-dien-3 beta-olMeSH
Cholesta-7,24-dien-3-ol, (3beta)-isomerMeSH
5alpha-Cholesta-7,24-dien-3beta-olHMDB
5alpha-Cholesta-7,24-diene-3beta-olHMDB
5α-Cholesta-7,24-diene-3β-olHMDB
Chemical FormulaC27H44O
Average Molecular Weight384.648
Monoisotopic Molecular Weight384.339216037
IUPAC Name(1R,2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol
Traditional Name(1R,2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol
CAS Registry Number651-54-7
SMILES
[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC=C(C)C
InChI Identifier
InChI=1S/C27H44O/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/h7,10,19-21,23-25,28H,6,8-9,11-17H2,1-5H3/t19-,20+,21+,23-,24+,25+,26+,27-/m1/s1
InChI KeyPKEPPDGGTSZLBL-SKCNUYALSA-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
  • Cholesterol
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-7-steroid
  • Delta-7-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point147 - 151 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00016 g/LALOGPS
logP10(7.4) g/LALOGPS
logP10(6.71) g/LChemAxon
logS10(-6.4) g/LALOGPS
pKa (Strongest Acidic)18.36ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity121.47 m³·mol⁻¹ChemAxon
Polarizability49.82 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5alpha-Cholesta-7,24-dien-3beta-ol[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC=C(C)C2685.6Standard polar33892256
5alpha-Cholesta-7,24-dien-3beta-ol[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC=C(C)C3179.2Standard non polar33892256
5alpha-Cholesta-7,24-dien-3beta-ol[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC=C(C)C3216.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5alpha-Cholesta-7,24-dien-3beta-ol,1TMS,isomer #1CC(C)=CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3269.3Semi standard non polar33892256
5alpha-Cholesta-7,24-dien-3beta-ol,1TBDMS,isomer #1CC(C)=CCC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3499.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Cholesta-7,24-dien-3beta-ol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholesta-7,24-dien-3beta-ol 10V, Positive-QTOFsplash10-000i-1009000000-c1e502b2b0de9645cff52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholesta-7,24-dien-3beta-ol 20V, Positive-QTOFsplash10-0a5c-9175000000-5a87d21ba3d15f6d6e542021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholesta-7,24-dien-3beta-ol 40V, Positive-QTOFsplash10-0a4l-9600000000-258a34962417211eae6b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholesta-7,24-dien-3beta-ol 10V, Negative-QTOFsplash10-001i-0009000000-4d7a5f3b63c0fb62f1d72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholesta-7,24-dien-3beta-ol 20V, Negative-QTOFsplash10-001i-0009000000-4d7a5f3b63c0fb62f1d72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholesta-7,24-dien-3beta-ol 40V, Negative-QTOFsplash10-001i-0009000000-cf419f92ab7dfef8f2f82021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024115
KNApSAcK IDNot Available
Chemspider ID4573588
KEGG Compound IDC05439
BioCyc ID5-ALPHA-CHOLESTA-724-DIEN-3-BETA-OL
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5928
PubChem Compound5459827
PDB IDNot Available
ChEBI ID16290
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceMoreau, Jacques P.; Aberhart, Donald J.; Caspi, Eliahu. Synthesis of 5a-cholesta-7,24-dien-3b-ol and cholesta-5,7,24-trien-3b-ol. Journal of Organic Chemistry (1974), 39(14), 2018-23.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in cholestenol delta-isomerase activity
Specific function:
Catalyzes the conversion of Delta(8)-sterols to their corresponding Delta(7)-isomers.
Gene Name:
EBP
Uniprot ID:
Q15125
Molecular weight:
26352.615
Reactions
Zymosterol intermediate 2 → 5alpha-Cholesta-7,24-dien-3beta-oldetails
General function:
Energy production and conversion
Specific function:
Catalyzes the reduction of the delta-24 double bond of sterol intermediates. Protects cells from oxidative stress by reducing caspase 3 activity during apoptosis induced by oxidative stress. Also protects against amyloid-beta peptide-induced apoptosis.
Gene Name:
DHCR24
Uniprot ID:
Q15392
Molecular weight:
60100.805
Reactions
Lathosterol + NADP → 5alpha-Cholesta-7,24-dien-3beta-ol + NADPH + Hydrogen Iondetails