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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-13 13:47:51 UTC
Update Date2022-03-07 02:49:33 UTC
HMDB IDHMDB0006851
Secondary Accession Numbers
  • HMDB06851
Metabolite Identification
Common Namedelta7-Avenasterol
Descriptiondelta7-Avenasterol, also known as 7-dehydroavenasterol or 24Z-ethylidenelathosterol, 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, delta7-avenasterol is considered to be a sterol lipid molecule. delta7-Avenasterol has been detected, but not quantified in, several different foods, such as garden onions, fenugreeks, vaccinium (blueberry, cranberry, huckleberry), grapefruit/pummelo hybrids, and pulses. This could make delta7-avenasterol a potential biomarker for the consumption of these foods. delta7-Avenasterol is an intermediate in the biosynthesis of steroids. It is the fourth to last step in the synthesis of stigmasterol and is converted from 24-ethylidenelophenol. It is then converted into 5-dehydroavenasterol via the enzyme lathosterol oxidase (EC 1.14.21.6).
Structure
Data?1593189445
Synonyms
ValueSource
7-DehydroavenasterolKEGG
Δ7-AvenasterolGenerator
(24Z)-24-Ethyl-5alpha-cholesta-7,24(28)-dien-3beta-olHMDB
(24Z)-5alpha-Stigmasta-7,24(28)-dien-3beta-olHMDB
(Z)-5alpha-Stigmasta-7,24(28)-dien-3beta-olHMDB
24Z-EthylidenelathosterolHMDB
3beta-Hydroxy-5alpha-stigmasta-7,24(28)Z-dieneHMDB
5alpha-Stigmasta-7,24(28)-dien-3-olHMDB
5alpha-Stigmasta-7,24(28)-dien-3beta-olHMDB
5alpha-Stigmasta-7,Z-24(28)-diene-3.beta-olHMDB
AvenasterolHMDB
Z-24-Ethylidene-5alpha-cholest-7-en-3beta-olHMDB
(24Z)-24-Ethyl-5α-cholesta-7,24(28)-dien-3β-olHMDB
(24Z)-5α-Stigmasta-7,24(28)-dien-3β-olHMDB
(3beta,5alpha,24Z)-Stigmasta-7,24(28)-dien-3-olHMDB
(3β,5α,24Z)-Stigmasta-7,24(28)-dien-3-olHMDB
(Z)-5α-Stigmasta-7,24(28)-dien-3β-olHMDB
3β-Hydroxy-5α-stigmasta-7,24(28)Z-dieneHMDB
5alpha-Stigmasta-7,Z-24(28)-diene-3beta-olHMDB
5α-Stigmasta-7,24(28)-dien-3-olHMDB
5α-Stigmasta-7,Z-24(28)-diene-3β-olHMDB
Z-24-Ethylidene-5α-cholest-7-en-3β-olHMDB
delta7-AvenasterolHMDB
Chemical FormulaC29H48O
Average Molecular Weight412.702
Monoisotopic Molecular Weight412.370516166
IUPAC Name(1R,2S,5S,7S,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}]heptadec-9-en-5-ol
Traditional Name(1R,2S,5S,7S,11R,14R,15R)-14-[(2R,5Z)-5-isopropylhept-5-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol
CAS Registry Number23290-26-8
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)CC\C(=C\C)C(C)C
InChI Identifier
InChI=1S/C29H48O/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/h7,11,19-20,22-23,25-27,30H,8-10,12-18H2,1-6H3/b21-7-/t20-,22+,23+,25-,26+,27+,28+,29-/m1/s1
InChI KeyMCWVPSBQQXUCTB-OQTIOYDCSA-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
  • Triterpenoid
  • Stigmastane-skeleton
  • 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
Disposition

Biological location

Source

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 Solubility9.2e-05 g/LALOGPS
logP7.62ALOGPS
logP7.44ChemAxon
logS-6.6ALOGPS
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 Count5ChemAxon
Refractivity130.62 m³·mol⁻¹ChemAxon
Polarizability53.66 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]+199.98631661259
DarkChem[M-H]-199.88131661259
DeepCCS[M-2H]-246.97230932474
DeepCCS[M+Na]+221.04230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
delta7-Avenasterol[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)CC\C(=C\C)C(C)C2793.3Standard polar33892256
delta7-Avenasterol[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)CC\C(=C\C)C(C)C3381.6Standard non polar33892256
delta7-Avenasterol[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)CC\C(=C\C)C(C)C3372.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
delta7-Avenasterol,1TMS,isomer #1C/C=C(/CC[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@@]21C)C(C)C3449.2Semi standard non polar33892256
delta7-Avenasterol,1TBDMS,isomer #1C/C=C(/CC[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@@]21C)C(C)C3677.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - delta7-Avenasterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f7k-1019000000-bccf5d01490277f0f41c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - delta7-Avenasterol GC-MS (1 TMS) - 70eV, Positivesplash10-06di-2104900000-4f71a97ae7d9183e13f12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - delta7-Avenasterol 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 - delta7-Avenasterol 10V, Positive-QTOFsplash10-01ot-1019500000-d9db27d1f0676bf070122017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta7-Avenasterol 20V, Positive-QTOFsplash10-0002-4149100000-10c29ad26226f06b51252017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta7-Avenasterol 40V, Positive-QTOFsplash10-0002-6197000000-0dad9f7452e27e74d08d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta7-Avenasterol 10V, Negative-QTOFsplash10-03di-0002900000-322cae85ce921a9ef9e22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta7-Avenasterol 20V, Negative-QTOFsplash10-03di-0005900000-7f1c49cc0c1fb7a57fb42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta7-Avenasterol 40V, Negative-QTOFsplash10-000t-2019000000-1b7f3a8af79353d7fab52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta7-Avenasterol 10V, Negative-QTOFsplash10-03di-0000900000-363450e12a0ea926276e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta7-Avenasterol 20V, Negative-QTOFsplash10-03di-0000900000-cc7acf42f15043b109102021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta7-Avenasterol 40V, Negative-QTOFsplash10-0a4i-1002900000-210aa86d26d8154c16912021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta7-Avenasterol 10V, Positive-QTOFsplash10-000i-0009000000-f7a69cb97e748b0859232021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta7-Avenasterol 20V, Positive-QTOFsplash10-0hgc-6249000000-91042d4ec3cdcf8772582021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta7-Avenasterol 40V, Positive-QTOFsplash10-0537-9310000000-7475a41fd48ab4cbf80d2021-09-23Wishart 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 IDFDB030685
KNApSAcK IDC00007322
Chemspider ID24850097
KEGG Compound IDC15782
BioCyc IDCPD-4125
BiGG IDNot Available
Wikipedia LinkAvenasterol
METLIN IDNot Available
PubChem Compound12795736
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