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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:00:11 UTC
Update Date2022-03-07 03:17:44 UTC
HMDB IDHMDB0060404
Secondary Accession Numbers
  • HMDB60404
Metabolite Identification
Common Name5,7,24(28)-Ergostatrienol
Description5,7,24(28)-Ergostatrienol 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. Based on a literature review a small amount of articles have been published on 5,7,24(28)-Ergostatrienol.
Structure
Data?1563866056
Synonyms
ValueSource
Ergosta-5,7,24(28)-trien-3beta-olHMDB
Ergosta-5,7,24(28)-trien-3b-olHMDB
Ergosta-5,7,24(28)-trien-3β-olHMDB
Chemical FormulaC28H44O
Average Molecular Weight396.6484
Monoisotopic Molecular Weight396.33921603
IUPAC Name(2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-ol
Traditional Name(2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-ol
CAS Registry NumberNot Available
SMILES
CC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C
InChI Identifier
InChI=1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9-10,18,20,22,24-26,29H,3,7-8,11-17H2,1-2,4-6H3/t20-,22+,24-,25+,26?,27+,28-/m1/s1
InChI KeyZEPNVCGPJXYABB-CPGDAPNVSA-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-5-steroid
  • 3-hydroxy-delta-7-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • 3-beta-hydroxysteroid
  • Delta-7-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0006 g/LALOGPS
logP7.64ALOGPS
logP6.65ChemAxon
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 Count5ChemAxon
Refractivity125.79 m³·mol⁻¹ChemAxon
Polarizability50.59 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+191.55731661259
DarkChem[M-H]-190.43831661259
DeepCCS[M-2H]-239.5230932474
DeepCCS[M+Na]+214.85630932474
AllCCS[M+H]+205.832859911
AllCCS[M+H-H2O]+203.632859911
AllCCS[M+NH4]+207.832859911
AllCCS[M+Na]+208.432859911
AllCCS[M-H]-206.232859911
AllCCS[M+Na-2H]-207.932859911
AllCCS[M+HCOO]-209.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5,7,24(28)-ErgostatrienolCC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C2883.3Standard polar33892256
5,7,24(28)-ErgostatrienolCC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C3196.7Standard non polar33892256
5,7,24(28)-ErgostatrienolCC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C3208.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5,7,24(28)-Ergostatrienol,1TMS,isomer #1C=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@@]21C)C(C)C3341.4Semi standard non polar33892256
5,7,24(28)-Ergostatrienol,1TBDMS,isomer #1C=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@@]21C)C(C)C3578.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5,7,24(28)-Ergostatrienol GC-MS (Non-derivatized) - 70eV, Positivesplash10-00lr-1019000000-03ea14fa853821e4638a2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,7,24(28)-Ergostatrienol GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-2005900000-497de544ef5aa67f52be2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,7,24(28)-Ergostatrienol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,7,24(28)-Ergostatrienol 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 - 5,7,24(28)-Ergostatrienol 10V, Positive-QTOFsplash10-004j-0019000000-ec4a863acd6783c7db802016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7,24(28)-Ergostatrienol 20V, Positive-QTOFsplash10-0032-6159000000-2fa2d066e8ea1504f2972016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7,24(28)-Ergostatrienol 40V, Positive-QTOFsplash10-001i-8094000000-e86c8d11fb643c8a6bd42016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7,24(28)-Ergostatrienol 10V, Negative-QTOFsplash10-0002-0009000000-03506c1fb18d95fe82ba2016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7,24(28)-Ergostatrienol 20V, Negative-QTOFsplash10-0002-0009000000-d3d2383799c5587a29c92016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7,24(28)-Ergostatrienol 40V, Negative-QTOFsplash10-004i-2019000000-180b0828fbb1ad3d49d92016-09-14Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDFDB030564
KNApSAcK IDNot Available
Chemspider ID30792038
KEGG Compound IDC16635
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10037499
PDB IDNot Available
ChEBI ID80095
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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. [PubMed:16902246 ]
  4. 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. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in iron ion binding
Specific function:
Catalyzes a dehydrogenation to introduce C5-6 double bond into lathosterol.
Gene Name:
SC5DL
Uniprot ID:
O75845
Molecular weight:
35300.55
Reactions
Episterol + NADP → 5,7,24(28)-Ergostatrienol + NADPH + Hydrogen Iondetails