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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:19:28 UTC
Update Date2022-03-07 02:51:21 UTC
HMDB IDHMDB0012116
Secondary Accession Numbers
  • HMDB0159998
  • HMDB12116
Metabolite Identification
Common Name5alpha-Campestan-3-one
Description5alpha-Campestan-3-one, also known as 3-dehydro-campestanol or methylcholestanone, 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, 5alpha-campestan-3-one is considered to be a sterol lipid molecule. 5alpha-Campestan-3-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5alpha-Campestan-3-one is involved in the brassinosteroid biosynthesis pathway. 5alpha-Campestan-3-one is produced from campest-4-en-3-one by the action of DET2 (EC 1.3.99.-), a probable steroid reductase. 5alpha-Campestan-3-one is then converted into campestanol or 22alpha-hydroxy-5alpha-campestan-3-one. The conversion to 22alpha-hydroxy-5alpha-campestan-3-one is catalyzed by DWF4, a steroid 22-alpha-hydroxylase (EC 1.14.13.-).
Structure
Data?1586448120
Synonyms
ValueSource
(24R)-24-Methyl-5alpha-cholestan-3-oneChEBI
(24R)-5alpha-Ergostan-3-oneChEBI
3-Dehydro-campestanolChEBI
Campestan-3-oneChEBI
MethylcholestanoneChEBI
(24R)-24-Methyl-5a-cholestan-3-oneGenerator
(24R)-24-Methyl-5α-cholestan-3-oneGenerator
(24R)-5a-Ergostan-3-oneGenerator
(24R)-5Α-ergostan-3-oneGenerator
5a-Campestan-3-oneGenerator
5Α-campestan-3-oneGenerator
(5alpha)-Campestan-3-oneHMDB
(5alpha,24R)-Ergostan-3-oneHMDB
(5Α)-campestan-3-oneHMDB
(5Α,24R)-ergostan-3-oneHMDB
OstreastanoneHMDB
5alpha-Campestan-3-oneHMDB
Chemical FormulaC28H48O
Average Molecular Weight400.691
Monoisotopic Molecular Weight400.370516166
IUPAC Name(1S,2S,7S,10R,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one
Traditional Name(1S,2S,7S,10R,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one
CAS Registry Number27212-88-0
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](C)C(C)C
InChI Identifier
InChI=1S/C28H48O/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/h18-21,23-26H,7-17H2,1-6H3/t19-,20-,21+,23+,24-,25+,26+,27+,28-/m1/s1
InChI KeyDDJMOMHMVFXEQF-JBQSTXLYSA-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-oxo-5-alpha-steroid
  • Oxosteroid
  • 3-oxosteroid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
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 Solubility1.2e-05 g/LALOGPS
logP6.41ALOGPS
logP8.01ChemAxon
logS-7.5ALOGPS
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity123.29 m³·mol⁻¹ChemAxon
Polarizability52.02 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]-232.39430932474
DeepCCS[M+Na]+206.35630932474
AllCCS[M+H]+206.032859911
AllCCS[M+H-H2O]+204.032859911
AllCCS[M+NH4]+207.832859911
AllCCS[M+Na]+208.332859911
AllCCS[M-H]-205.532859911
AllCCS[M+Na-2H]-207.532859911
AllCCS[M+HCOO]-209.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5alpha-Campestan-3-one[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](C)C(C)C2723.1Standard polar33892256
5alpha-Campestan-3-one[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](C)C(C)C3200.1Standard non polar33892256
5alpha-Campestan-3-one[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](C)C(C)C3292.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5alpha-Campestan-3-one,1TMS,isomer #1CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3236.8Semi standard non polar33892256
5alpha-Campestan-3-one,1TMS,isomer #1CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3186.0Standard non polar33892256
5alpha-Campestan-3-one,1TMS,isomer #1CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3477.6Standard polar33892256
5alpha-Campestan-3-one,1TMS,isomer #2CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3223.2Semi standard non polar33892256
5alpha-Campestan-3-one,1TMS,isomer #2CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3243.2Standard non polar33892256
5alpha-Campestan-3-one,1TMS,isomer #2CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3476.9Standard polar33892256
5alpha-Campestan-3-one,1TBDMS,isomer #1CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3477.2Semi standard non polar33892256
5alpha-Campestan-3-one,1TBDMS,isomer #1CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3360.4Standard non polar33892256
5alpha-Campestan-3-one,1TBDMS,isomer #1CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3596.1Standard polar33892256
5alpha-Campestan-3-one,1TBDMS,isomer #2CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3458.8Semi standard non polar33892256
5alpha-Campestan-3-one,1TBDMS,isomer #2CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3421.4Standard non polar33892256
5alpha-Campestan-3-one,1TBDMS,isomer #2CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C=C(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3597.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Campestan-3-one GC-MS (1 TMS) - 70eV, PositiveNot Available2020-06-30Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Campestan-3-one GC-MS (1 TMS) - 70eV, PositiveNot Available2020-06-30Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Campestan-3-one 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 - 5alpha-Campestan-3-one 10V, Positive-QTOFNot Available2020-06-30Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Campestan-3-one 20V, Positive-QTOFNot Available2020-06-30Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Campestan-3-one 40V, Positive-QTOFNot Available2020-06-30Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Campestan-3-one 10V, Negative-QTOFNot Available2020-06-30Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Campestan-3-one 20V, Negative-QTOFNot Available2020-06-30Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Campestan-3-one 40V, Negative-QTOFNot Available2020-06-30Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Campestan-3-one 10V, Positive-QTOFsplash10-0udi-1005900000-23d594e78fcce0c6d9502021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Campestan-3-one 20V, Positive-QTOFsplash10-0a59-9244000000-b241f03a2271db9de36b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Campestan-3-one 40V, Positive-QTOFsplash10-000x-9610000000-a3da091d12c7e9de70202021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Campestan-3-one 10V, Negative-QTOFsplash10-0002-0009000000-e5e9af9914ac05de1a5c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Campestan-3-one 20V, Negative-QTOFsplash10-0002-0009000000-e5e9af9914ac05de1a5c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Campestan-3-one 40V, Negative-QTOFsplash10-0002-0009000000-c77fc5906d5d7fb274ed2021-09-23Wishart 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 IDFDB112394
KNApSAcK IDNot Available
Chemspider ID17221007
KEGG Compound IDC15786
BioCyc IDCPD-709
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16061343
PDB IDNot Available
ChEBI ID18533
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.