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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-13 13:49:58 UTC
Update Date2022-03-07 02:49:34 UTC
HMDB IDHMDB0006852
Secondary Accession Numbers
  • HMDB06852
Metabolite Identification
Common Name5-Dehydroavenasterol
Description5-Dehydroavenasterol belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Thus, 5-dehydroavenasterol is considered to be a sterol lipid molecule. 5-Dehydroavenasterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5-Dehydroavenasterol is an intermediate in the biosynthesis of steroids. It is the third to last step in the synthesis of stigmasterol and is converted from delta 7-avenasterol via the enzyme lathosterol oxidase (EC 1.14.21.6). It is then converted into Isofucosterol via the enzyme 7-dehydrocholesterol reductase (EC 1.3.1.21).
Structure
Data?1583941359
Synonyms
ValueSource
(24Z)-24-Ethylcholesta-5,7,24(28)-trien-3beta-olHMDB
(24Z)-24-Ethylcholesta-5,7,24(28)-trien-3β-olHMDB
(24Z)-Stigmasta-5,7,24(28)-trien-3beta-olHMDB
(24Z)-Stigmasta-5,7,24(28)-trien-3β-olHMDB
(3beta,24Z)-Stigmasta-5,7,24(28)-trien-3-olHMDB
(3Β,24Z)-stigmasta-5,7,24(28)-trien-3-olHMDB
24Z-Ethylidenecholesta-5,7-dien-3beta-olHMDB
24Z-Ethylidenecholesta-5,7-dien-3β-olHMDB
7-DehydroisofucosterolHMDB
Stigmasta-5,7-cis-24(28)-trien-3beta-olHMDB
Stigmasta-5,7-cis-24(28)-trien-3β-olHMDB
5-DehydroavenasterolHMDB
Chemical FormulaC29H46O
Average Molecular Weight410.686
Monoisotopic Molecular Weight410.354866101
IUPAC Name(1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R,5Z)-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol
Traditional Name(1S,2R,5S,11R,14R,15R)-14-[(2R,5Z)-5-isopropylhept-5-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol
CAS Registry Number29560-28-9
SMILES
[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC\C(=C\C)C(C)C
InChI Identifier
InChI=1S/C29H46O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h7,10-11,19-20,23,25-27,30H,8-9,12-18H2,1-6H3/b21-7-/t20-,23+,25-,26+,27+,28+,29-/m1/s1
InChI KeyXPRWWANUPMYKMF-HVEGQNEHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassStigmastanes and derivatives
Direct ParentStigmastanes and derivatives
Alternative Parents
Substituents
  • Stigmastane-skeleton
  • Triterpenoid
  • 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
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
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 Solubility0.00026 g/LALOGPS
logP8.24ALOGPS
logP7.03ChemAxon
logS-6.2ALOGPS
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
Refractivity131.47 m³·mol⁻¹ChemAxon
Polarizability52.88 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
DeepCCS[M-2H]-248.65930932474
DeepCCS[M+Na]+223.09130932474
AllCCS[M+H]+209.232859911
AllCCS[M+H-H2O]+207.132859911
AllCCS[M+NH4]+211.032859911
AllCCS[M+Na]+211.632859911
AllCCS[M-H]-208.632859911
AllCCS[M+Na-2H]-210.532859911
AllCCS[M+HCOO]-212.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Dehydroavenasterol[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC\C(=C\C)C(C)C3123.5Standard polar33892256
5-Dehydroavenasterol[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC\C(=C\C)C(C)C3334.2Standard non polar33892256
5-Dehydroavenasterol[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC\C(=C\C)C(C)C3301.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Dehydroavenasterol,1TMS,isomer #1C/C=C(/CC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C3454.3Semi standard non polar33892256
5-Dehydroavenasterol,1TBDMS,isomer #1C/C=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)[C@H]3CC[C@@]21C)C(C)C3688.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Dehydroavenasterol GC-MS (1 TMS) - 70eV, PositiveNot Available2020-06-30Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Dehydroavenasterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Dehydroavenasterol 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-Dehydroavenasterol 10V, Positive-QTOFNot Available2020-06-30Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Dehydroavenasterol 20V, Positive-QTOFNot Available2020-06-30Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Dehydroavenasterol 40V, Positive-QTOFNot Available2020-06-30Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Dehydroavenasterol 10V, Negative-QTOFNot Available2020-06-30Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Dehydroavenasterol 20V, Negative-QTOFNot Available2020-06-30Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Dehydroavenasterol 40V, Negative-QTOFNot Available2020-06-30Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Dehydroavenasterol 10V, Positive-QTOFsplash10-00lr-0009000000-0f8b3e625297324cedfc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Dehydroavenasterol 20V, Positive-QTOFsplash10-0gbi-3049000000-2747d1c8268b883ffc0f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Dehydroavenasterol 40V, Positive-QTOFsplash10-0a5c-9240000000-e3ed5ab4d8f8f2bdf5b22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Dehydroavenasterol 10V, Negative-QTOFsplash10-0a4i-0000900000-84eae2c8ad8ccafd77412021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Dehydroavenasterol 20V, Negative-QTOFsplash10-0a4i-0000900000-3ef7712cbccd003ba1442021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Dehydroavenasterol 40V, Negative-QTOFsplash10-0a4i-1002900000-c36e120707d7a0c2343a2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB024118
KNApSAcK IDC00007527
Chemspider IDNot Available
KEGG Compound IDC15783
BioCyc IDCPD-4126
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44263331
PDB IDNot Available
ChEBI IDNot Available
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 ReferencesNot Available

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
delta7-Avenasterol → 5-Dehydroavenasteroldetails
General function:
Involved in 7-dehydrocholesterol reductase activity
Specific function:
Production of cholesterol by reduction of C7-C8 double bond of 7-dehydrocholesterol (7-DHC).
Gene Name:
DHCR7
Uniprot ID:
Q9UBM7
Molecular weight:
54488.98
Reactions
5-Dehydroavenasterol → Isofucosteroldetails