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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-09-05 15:29:19 UTC
Update Date2022-03-07 02:49:34 UTC
HMDB IDHMDB0006928
Secondary Accession Numbers
  • HMDB0006844
  • HMDB0011607
  • HMDB06844
  • HMDB06928
  • HMDB11607
Metabolite Identification
Common Namedelta8,14-Sterol
Descriptiondelta8,14-Sterol, also known as 4alpha-methyl-5alpha-ergosta-8,14,24(28)-trien-3beta-ol, 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. Thus, delta8,14-sterol is considered to be a sterol lipid molecule. delta8,14-Sterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. delta8,14-Sterol is an intermediate in the biosynthesis of steroids and is converted from O-butusifoliol via the enzyme cytochrome P450, family 51, subfamily A (sterol 14-demethylase) (EC 1.14.13.70). It is then converted into 4-alpha-methylfecosterol via the enzyme delta14-sterol reductase (EC 1.3.1.70).
Structure
Data?1588268295
Synonyms
ValueSource
delta8,14 -SterolChEBI
delta8,14-SterolChEBI
Δ8,14 -sterolGenerator
Δ8,14-sterolGenerator
Δ 8,14 -sterolGenerator
4-alpha-Methyl-5-alpha-ergosta-8,14,24(28)-trien-3-beta-olHMDB
4a-Methyl-5a-ergosta-8,14,24(28)-trien-3b-olHMDB
4a-Methylergosta-8,14,24(241)-trien-3b-olHMDB
4alpha-Methyl-5alpha-ergosta-8,14,24(28)-trien-3beta-olHMDB
(3beta,4alpha,5alpha)-4-Methylergosta-8,14,24(28)-trien-3-olHMDB
(3β,4α,5α)-4-Methylergosta-8,14,24(28)-trien-3-olHMDB
4alpha-Methylergosta-8,14,24(241)-trien-3beta-olHMDB
4α-Methyl-5α-ergosta-8,14,24(28)-trien-3β-olHMDB
4α-Methylergosta-8,14,24(241)-trien-3β-olHMDB
Chemical FormulaC29H46O
Average Molecular Weight410.6749
Monoisotopic Molecular Weight410.354866094
IUPAC Name(2S,5S,6S,7S,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-5-ol
Traditional Name(2S,5S,6S,7S,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-5-ol
CAS Registry Number74635-33-9
SMILES
[H][C@@]1(CC=C2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC(=C)C(C)C
InChI Identifier
InChI=1S/C29H46O/c1-18(2)19(3)8-9-20(4)23-12-13-25-22-10-11-24-21(5)27(30)15-17-29(24,7)26(22)14-16-28(23,25)6/h13,18,20-21,23-24,27,30H,3,8-12,14-17H2,1-2,4-7H3/t20-,21+,23-,24+,27+,28-,29+/m1/s1
InChI KeyHLAWVOWADPNAGN-BAHZUFOISA-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-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 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

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 Solubility0.0016 g/LALOGPS
logP7ALOGPS
logP6.97ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)18.96ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity130 m³·mol⁻¹ChemAxon
Polarizability53.06 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]+200.53431661259
DarkChem[M-H]-201.77731661259
DeepCCS[M-2H]-243.21230932474
DeepCCS[M+Na]+217.53530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
delta8,14-Sterol[H][C@@]1(CC=C2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC(=C)C(C)C3298.5Standard polar33892256
delta8,14-Sterol[H][C@@]1(CC=C2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC(=C)C(C)C3290.1Standard non polar33892256
delta8,14-Sterol[H][C@@]1(CC=C2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC(=C)C(C)C3315.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
delta8,14-Sterol,1TMS,isomer #1C=C(CC[C@@H](C)[C@H]1CC=C2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)[C@@H](C)[C@@H]1CC3)C(C)C3191.8Semi standard non polar33892256
delta8,14-Sterol,1TBDMS,isomer #1C=C(CC[C@@H](C)[C@H]1CC=C2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)[C@@H]1CC3)C(C)C3441.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - delta8,14-Sterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-0009000000-3be06a7a2e1d781b5fa82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - delta8,14-Sterol GC-MS (1 TMS) - 70eV, Positivesplash10-0gb9-2003900000-1ddc0b2fd8c5c50509032017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - delta8,14-Sterol 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 - delta8,14-Sterol 10V, Positive-QTOFsplash10-01ox-1019500000-046d99a719521520a2212016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta8,14-Sterol 20V, Positive-QTOFsplash10-053u-5239100000-35e12a7ac241ea6b3d5e2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta8,14-Sterol 40V, Positive-QTOFsplash10-05o0-7179000000-157b7d71a0b50a4f6cfa2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta8,14-Sterol 10V, Negative-QTOFsplash10-0a4i-0002900000-3112227426dc5f73b5982016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta8,14-Sterol 20V, Negative-QTOFsplash10-0a4i-0004900000-6302f767a4949cfeabe02016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta8,14-Sterol 40V, Negative-QTOFsplash10-0006-2009000000-1068ac4ee572fe372b162016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta8,14-Sterol 10V, Positive-QTOFsplash10-02t9-0079400000-909cacfa5264a8b970532021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta8,14-Sterol 20V, Positive-QTOFsplash10-014i-5295000000-8fdfbe980fb0780691312021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta8,14-Sterol 40V, Positive-QTOFsplash10-014u-9431000000-dd7d0e22284f4ddcce4c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta8,14-Sterol 10V, Negative-QTOFsplash10-0a4i-0000900000-84eae2c8ad8ccafd77412021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta8,14-Sterol 20V, Negative-QTOFsplash10-0a4i-0000900000-bf8e63a2888265bea2de2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta8,14-Sterol 40V, Negative-QTOFsplash10-0a4i-0001900000-7b92331f9804da3440ed2021-09-22Wishart 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 IDFDB011216
KNApSAcK IDC00007523
Chemspider ID391501
KEGG Compound IDC11508
BioCyc IDALPHA-METHYL-5-ALPHA-ERGOSTA
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound443237
PDB IDNot Available
ChEBI ID30109
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 delta14-sterol reductase activity
Specific function:
Involved in the conversion of lanosterol to cholesterol.
Gene Name:
TM7SF2
Uniprot ID:
O76062
Molecular weight:
46405.345
Reactions
delta8,14-Sterol + NADPH + Hydrogen Ion → 4alpha-Methylfecosterol + NADPdetails
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes C14-demethylation of lanosterol; it transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
Gene Name:
CYP51A1
Uniprot ID:
Q16850
Molecular weight:
57277.81
Reactions
Obtusifoliol + Oxygen + NADPH → delta8,14-Sterol + Formic acid + NADP + Waterdetails
Obtusifoliol + Oxygen + NADPH + Hydrogen Ion → delta8,14-Sterol + Formic acid + NADP + Waterdetails