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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:19:02 UTC
HMDB IDHMDB0001242
Secondary Accession Numbers
  • HMDB0006843
  • HMDB01242
  • HMDB06843
Metabolite Identification
Common NameObtusifoliol
DescriptionObtusifoliol 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, obtusifoliol is considered to be a sterol lipid molecule. Obtusifoliol is found, on average, in the highest concentration within evening primroses. Obtusifoliol has also been detected, but not quantified in, several different foods, such as common chokecherries, jicama, pepper (C. frutescens), avocado, and pecan nuts. This could make obtusifoliol a potential biomarker for the consumption of these foods. Obtusifoliol is an intermediate in the biosynthesis of cholesterol: in a reaction catalyzed by the enzyme CYP51A1 (EC 1.14.13.70, sterol 14-demethylase) (PMID: 9559662 ). CYP51A1 is a housekeeping enzyme essential for the viability of mammals, an essential step in cholesterol biosynthesis. Sterol 14-demethylation occurs in all organisms exhibiting de novo sterol biosynthesis and CYP51A1 has been conserved throughout evolution (PMID: 8797093 ).
Structure
Data?1594046570
Synonyms
ValueSource
4alpha,14alpha-Dimethyl-5alpha-ergosta-8,24(28)-dien-3beta-olKEGG
4alpha,14alpha-Dimethyl-24-methylene-5alpha-cholesta-8-en-3beta-olKEGG
4a,14a-Dimethyl-5a-ergosta-8,24(28)-dien-3b-olGenerator
4α,14α-Dimethyl-5α-ergosta-8,24(28)-dien-3β-olGenerator
4a,14a-Dimethyl-24-methylene-5a-cholesta-8-en-3b-olGenerator
4α,14α-Dimethyl-24-methylene-5α-cholesta-8-en-3β-olGenerator
(+)-ObtusifoliolHMDB
(3beta,4alpha,5alpha)-4,14-Dimethylergosta-8,24(28)-dien-3-olHMDB
(3β,4α,5α)-4,14-Dimethylergosta-8,24(28)-dien-3-olHMDB
4alpha,14alpha-Dimethyl-delta8,24(28)-ergostadien-3beta-olHMDB
4α,14α-Dimethyl-Δ8,24(28)-ergostadien-3β-olHMDB
ObtusifoliolHMDB
Chemical FormulaC30H50O
Average Molecular Weight426.7174
Monoisotopic Molecular Weight426.386166222
IUPAC Name(2S,5S,6S,7S,11R,14R,15R)-2,6,11,15-tetramethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
Traditional Name(2S,5S,6S,7S,11R,14R,15R)-2,6,11,15-tetramethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
CAS Registry Number16910-32-0
SMILES
[H][C@@]1(CC[C@@]2(C)C3=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/C30H50O/c1-19(2)20(3)9-10-21(4)23-13-17-30(8)26-12-11-24-22(5)27(31)15-16-28(24,6)25(26)14-18-29(23,30)7/h19,21-24,27,31H,3,9-18H2,1-2,4-8H3/t21-,22+,23-,24+,27+,28+,29-,30+/m1/s1
InChI KeyMMNYKQIDRZNIKT-VSADUBDNSA-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
  • 14-alpha-methylsteroid
  • 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
  • Ergosterols and C24-methyl derivatives (C01943 )
  • Ergosterols and C24-methyl derivatives (LMST01030101 )
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0018 g/LALOGPS
logP10(7.25) g/LALOGPS
logP10(7.67) g/LChemAxon
logS10(-6) g/LALOGPS
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
Refractivity133.62 m³·mol⁻¹ChemAxon
Polarizability54.99 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Obtusifoliol,1TMS,#1C=C(CC[C@@H](C)[C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)[C@@H](C)[C@@H]1CC3)C(C)C3350.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Obtusifoliol,1TBDMS,#1C=C(CC[C@@H](C)[C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)[C@@H]1CC3)C(C)C3570.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Obtusifoliol GC-MS (1 TMS)splash10-0a5c-4910000000-dad41d67ee45a726de742014-06-16HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Obtusifoliol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Obtusifoliol 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 - Obtusifoliol 10V, Positive-QTOFsplash10-056r-1003900000-3974cb418cf053c4e3282016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Obtusifoliol 20V, Positive-QTOFsplash10-0560-7139400000-dfd6daa4b47fe2be34cf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Obtusifoliol 40V, Positive-QTOFsplash10-00lr-9187100000-7ee2f7d49200d2ca6ea22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Obtusifoliol 10V, Negative-QTOFsplash10-004i-0000900000-e7093af21e32d58948802016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Obtusifoliol 20V, Negative-QTOFsplash10-004i-0000900000-8428ae6beee69ce08d962016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Obtusifoliol 40V, Negative-QTOFsplash10-0a4i-3009700000-ae79d303adb71352d4252016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Obtusifoliol 10V, Negative-QTOFsplash10-004i-0000900000-590c9e4adfdd12b64d932021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Obtusifoliol 20V, Negative-QTOFsplash10-004i-0000900000-da03ad21be78071c2fd82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Obtusifoliol 40V, Negative-QTOFsplash10-00fr-1005900000-ddc6e9faaf47d2ff67362021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Obtusifoliol 10V, Positive-QTOFsplash10-001i-9138200000-b48da05273d106ecd79a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Obtusifoliol 20V, Positive-QTOFsplash10-053r-9211000000-c7a30944f787b77be55c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Obtusifoliol 40V, Positive-QTOFsplash10-001l-9431000000-fc81973855911f7a57822021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • 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 IDFDB004683
KNApSAcK IDC00007368
Chemspider ID58745
KEGG Compound IDC01943
BioCyc IDOBTUSIFOLIOL
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6102
PubChem Compound65252
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 References
  1. Aoyama Y, Noshiro M, Gotoh O, Imaoka S, Funae Y, Kurosawa N, Horiuchi T, Yoshida Y: Sterol 14-demethylase P450 (P45014DM*) is one of the most ancient and conserved P450 species. J Biochem. 1996 May;119(5):926-33. [PubMed:8797093 ]
  2. Lamb DC, Kelly DE, Kelly SL: Molecular diversity of sterol 14alpha-demethylase substrates in plants, fungi and humans. FEBS Lett. 1998 Mar 27;425(2):263-5. [PubMed:9559662 ]

Enzymes

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