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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:20:50 UTC
Update Date2022-03-07 02:51:22 UTC
HMDB IDHMDB0012196
Secondary Accession Numbers
  • HMDB12196
Metabolite Identification
Common NameCampest-4-en-3-one
DescriptionCampest-4-en-3-one is an intermediate in Brassinolide Biosynthesis pathway.The conversion of the membrane Sterol Campesterol to BL occurs via a series of reductions, hydroxylations, epimerizations and oxidations that have been extensively studied in several species. The conversion of Campesterol to Campestanol is not a single step, but composed of the biosynthetic sequence of Campesterol 4-en-3Beta-ol ---> 4-en-3-one ---> 3-one ---> Campestanol in Arabidopsis. In the first step, Campesterol is converted to Campest-4-en-3Beta-ol in presence of enzyme Delta-5-3-Ketosteroid Isomerase. Enzymes that catalyze the conversion from 3-Beta-Hydroxy-Delta,5-6-Steroid to 3-oxo-Delta-4-5 Isomerase have been reported in Bacteria and Mammals. Campest-4-en-3 Beta-ol is converted to Campest-4-en-3-one in presence of enzyme 3-Beta-Hydroxysteroid Dehydrogenase. In the next step, Campest-4-en-3-one is converted to Campestanol via 5-Alpha-Campestan-3-one. 3-Oxo-5Alpha-Steroid 4-Dehydrogenase family members (encoded by Det2 in Arabidopsis) catalyze the formation of 5-Alpha-Campestan-3-one.
Structure
Data?1595010179
Synonyms
ValueSource
(24R)-Ergost-4-en-3-oneChEBI
(24R)-24-Methyl-cholest-4-en-3-oneHMDB
3-Dehydro-delta4-5-campesterolHMDB
3-Dehydro-Δ4-5-campesterolHMDB
Campest-4-en-3-oneHMDB
MethylcholestenoneHMDB
Chemical FormulaC28H46O
Average Molecular Weight398.6642
Monoisotopic Molecular Weight398.354866094
IUPAC Name(1S,2R,10S,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional Name(1S,2R,10S,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
CAS Registry Number22260-46-4
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=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/C28H46O/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/h17-20,23-26H,7-16H2,1-6H3/t19-,20-,23+,24-,25+,26+,27+,28-/m1/s1
InChI KeyQQIOPZFVTIHASB-IMUDCKKOSA-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
  • Oxosteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Cyclohexenone
  • 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
Disposition
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 Solubility1.9e-05 g/LALOGPS
logP6.4ALOGPS
logP7.97ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)19.09ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity124.11 m³·mol⁻¹ChemAxon
Polarizability51.48 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]-234.53230932474
DeepCCS[M+Na]+208.96630932474
AllCCS[M+H]+205.532859911
AllCCS[M+H-H2O]+203.432859911
AllCCS[M+NH4]+207.532859911
AllCCS[M+Na]+208.032859911
AllCCS[M-H]-206.432859911
AllCCS[M+Na-2H]-208.332859911
AllCCS[M+HCOO]-210.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Campest-4-en-3-one[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](C)C(C)C3775.7Standard polar33892256
Campest-4-en-3-one[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](C)C(C)C3252.2Standard non polar33892256
Campest-4-en-3-one[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](C)C(C)C3372.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Campest-4-en-3-one,1TMS,isomer #1CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3297.8Semi standard non polar33892256
Campest-4-en-3-one,1TMS,isomer #1CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3333.1Standard non polar33892256
Campest-4-en-3-one,1TMS,isomer #1CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3485.2Standard polar33892256
Campest-4-en-3-one,1TBDMS,isomer #1CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3526.8Semi standard non polar33892256
Campest-4-en-3-one,1TBDMS,isomer #1CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3535.7Standard non polar33892256
Campest-4-en-3-one,1TBDMS,isomer #1CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3609.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Campest-4-en-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 - Campest-4-en-3-one 10V, Positive-QTOFsplash10-0002-1019000000-1fed4375ad249602c5ec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campest-4-en-3-one 20V, Positive-QTOFsplash10-06rj-6119000000-84dbd57823d0c0ce11ed2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campest-4-en-3-one 40V, Positive-QTOFsplash10-0019-9155000000-65bf4cb9835a9a1e4b932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campest-4-en-3-one 10V, Negative-QTOFsplash10-0002-0009000000-e91dc76e684347b42d892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campest-4-en-3-one 20V, Negative-QTOFsplash10-0002-0009000000-54beea4bb3f336ae1aba2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campest-4-en-3-one 40V, Negative-QTOFsplash10-001i-2019000000-664968980c2bbb76cfde2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campest-4-en-3-one 10V, Positive-QTOFsplash10-0002-0019000000-0739b104e2d4c8225b3a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campest-4-en-3-one 20V, Positive-QTOFsplash10-05fr-9246000000-490c7f71f17f3d18ffc52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campest-4-en-3-one 40V, Positive-QTOFsplash10-0536-9310000000-a4b7a3174e57264e35082021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campest-4-en-3-one 10V, Negative-QTOFsplash10-0002-0009000000-0ca06bc1a59e9690d9392021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campest-4-en-3-one 20V, Negative-QTOFsplash10-0002-0009000000-0ca06bc1a59e9690d9392021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campest-4-en-3-one 40V, Negative-QTOFsplash10-0002-0009000000-d8b47ff315ada5239c0d2021-09-24Wishart 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 IDFDB018055
KNApSAcK IDC00007514
Chemspider ID10160746
KEGG Compound IDC15785
BioCyc IDCPD-698
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11988279
PDB IDNot Available
ChEBI ID18534
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.

Enzymes

General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. HSD VII is active against four 7-alpha-hydroxylated sterols. Does not metabolize several different C(19/21) steroids as substrates. Involved in bile acid synthesis.
Gene Name:
HSD3B7
Uniprot ID:
Q9H2F3
Molecular weight:
21322.265