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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:46:50 UTC
Update Date2022-03-07 02:56:53 UTC
HMDB IDHMDB0041130
Secondary Accession Numbers
  • HMDB41130
Metabolite Identification
Common Name24-Epibrassinolide
Description24-Epibrassinolide belongs to the class of organic compounds known as brassinolides and derivatives. These are cholestane based steroid lactones containing benzo[c]indeno[5,4-e]oxepin-3-one. 24-Epibrassinolide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563863627
Synonyms
ValueSource
Epibrassinolide RHMDB
2alpha,3alpha,22alpha,23alpha-Tetrahydroxy-24alpha-methyl-b-homo-7-oxa-5alpha-cholestan-6-oneHMDB
BrassinolideHMDB
Brassinolide, (2alpha,3alpha,5alpha,22S,23S)-isomerHMDB
Brassinolide, (2alpha,3alpha,5alpha.22R,23R)-isomerHMDB
24-EpibrassinolideMeSH
Chemical FormulaC28H48O6
Average Molecular Weight480.6771
Monoisotopic Molecular Weight480.345089268
IUPAC Name15-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-4,5-dihydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one
Traditional Name15-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-4,5-dihydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one
CAS Registry Number78821-43-9
SMILES
CC(C)C(C)C(O)C(O)C(C)C1CCC2C3COC(=O)C4CC(O)C(O)CC4(C)C3CCC12C
InChI Identifier
InChI=1S/C28H48O6/c1-14(2)15(3)24(31)25(32)16(4)18-7-8-19-17-13-34-26(33)21-11-22(29)23(30)12-28(21,6)20(17)9-10-27(18,19)5/h14-25,29-32H,7-13H2,1-6H3
InChI KeyIXVMHGVQKLDRKH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as brassinolides and derivatives. These are cholestane based steroid lactones containing benzo[c]indeno[5,4-e]oxepin-3-one.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentBrassinolides and derivatives
Alternative Parents
Substituents
  • Brassinolide-skeleton
  • Caprolactone
  • Oxepane
  • Cyclic alcohol
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point256 - 258 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.034 g/LALOGPS
logP2.5ALOGPS
logP3.13ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)13.45ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity130.41 m³·mol⁻¹ChemAxon
Polarizability56 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+210.49531661259
DarkChem[M-H]-202.72631661259
DeepCCS[M-2H]-243.75430932474
DeepCCS[M+Na]+218.90730932474
AllCCS[M+H]+217.332859911
AllCCS[M+H-H2O]+215.632859911
AllCCS[M+NH4]+218.832859911
AllCCS[M+Na]+219.232859911
AllCCS[M-H]-213.632859911
AllCCS[M+Na-2H]-216.232859911
AllCCS[M+HCOO]-219.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
24-EpibrassinolideCC(C)C(C)C(O)C(O)C(C)C1CCC2C3COC(=O)C4CC(O)C(O)CC4(C)C3CCC12C3202.1Standard polar33892256
24-EpibrassinolideCC(C)C(C)C(O)C(O)C(C)C1CCC2C3COC(=O)C4CC(O)C(O)CC4(C)C3CCC12C3260.0Standard non polar33892256
24-EpibrassinolideCC(C)C(C)C(O)C(O)C(C)C1CCC2C3COC(=O)C4CC(O)C(O)CC4(C)C3CCC12C3975.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
24-Epibrassinolide,1TMS,isomer #1CC(C)C(C)C(O[Si](C)(C)C)C(O)C(C)C1CCC2C3COC(=O)C4CC(O)C(O)CC4(C)C3CCC12C3999.7Semi standard non polar33892256
24-Epibrassinolide,1TMS,isomer #2CC(C)C(C)C(O)C(O[Si](C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O)C(O)CC4(C)C3CCC12C3994.1Semi standard non polar33892256
24-Epibrassinolide,1TMS,isomer #3CC(C)C(C)C(O)C(O)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C)C(O)CC4(C)C3CCC12C4024.9Semi standard non polar33892256
24-Epibrassinolide,1TMS,isomer #4CC(C)C(C)C(O)C(O)C(C)C1CCC2C3COC(=O)C4CC(O)C(O[Si](C)(C)C)CC4(C)C3CCC12C4030.0Semi standard non polar33892256
24-Epibrassinolide,2TMS,isomer #1CC(C)C(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O)C(O)CC4(C)C3CCC12C3927.1Semi standard non polar33892256
24-Epibrassinolide,2TMS,isomer #2CC(C)C(C)C(O[Si](C)(C)C)C(O)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C)C(O)CC4(C)C3CCC12C3920.2Semi standard non polar33892256
24-Epibrassinolide,2TMS,isomer #3CC(C)C(C)C(O[Si](C)(C)C)C(O)C(C)C1CCC2C3COC(=O)C4CC(O)C(O[Si](C)(C)C)CC4(C)C3CCC12C3900.7Semi standard non polar33892256
24-Epibrassinolide,2TMS,isomer #4CC(C)C(C)C(O)C(O[Si](C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C)C(O)CC4(C)C3CCC12C3901.4Semi standard non polar33892256
24-Epibrassinolide,2TMS,isomer #5CC(C)C(C)C(O)C(O[Si](C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O)C(O[Si](C)(C)C)CC4(C)C3CCC12C3887.4Semi standard non polar33892256
24-Epibrassinolide,2TMS,isomer #6CC(C)C(C)C(O)C(O)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C)C(O[Si](C)(C)C)CC4(C)C3CCC12C4042.5Semi standard non polar33892256
24-Epibrassinolide,3TMS,isomer #1CC(C)C(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C)C(O)CC4(C)C3CCC12C3763.7Semi standard non polar33892256
24-Epibrassinolide,3TMS,isomer #2CC(C)C(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O)C(O[Si](C)(C)C)CC4(C)C3CCC12C3750.1Semi standard non polar33892256
24-Epibrassinolide,3TMS,isomer #3CC(C)C(C)C(O[Si](C)(C)C)C(O)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C)C(O[Si](C)(C)C)CC4(C)C3CCC12C3816.1Semi standard non polar33892256
24-Epibrassinolide,3TMS,isomer #4CC(C)C(C)C(O)C(O[Si](C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C)C(O[Si](C)(C)C)CC4(C)C3CCC12C3809.5Semi standard non polar33892256
24-Epibrassinolide,4TMS,isomer #1CC(C)C(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C)C(O[Si](C)(C)C)CC4(C)C3CCC12C3664.9Semi standard non polar33892256
24-Epibrassinolide,1TBDMS,isomer #1CC(C)C(C)C(O[Si](C)(C)C(C)(C)C)C(O)C(C)C1CCC2C3COC(=O)C4CC(O)C(O)CC4(C)C3CCC12C4219.2Semi standard non polar33892256
24-Epibrassinolide,1TBDMS,isomer #2CC(C)C(C)C(O)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O)C(O)CC4(C)C3CCC12C4212.9Semi standard non polar33892256
24-Epibrassinolide,1TBDMS,isomer #3CC(C)C(C)C(O)C(O)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C(C)(C)C)C(O)CC4(C)C3CCC12C4244.0Semi standard non polar33892256
24-Epibrassinolide,1TBDMS,isomer #4CC(C)C(C)C(O)C(O)C(C)C1CCC2C3COC(=O)C4CC(O)C(O[Si](C)(C)C(C)(C)C)CC4(C)C3CCC12C4253.1Semi standard non polar33892256
24-Epibrassinolide,2TBDMS,isomer #1CC(C)C(C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O)C(O)CC4(C)C3CCC12C4373.7Semi standard non polar33892256
24-Epibrassinolide,2TBDMS,isomer #2CC(C)C(C)C(O[Si](C)(C)C(C)(C)C)C(O)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C(C)(C)C)C(O)CC4(C)C3CCC12C4357.9Semi standard non polar33892256
24-Epibrassinolide,2TBDMS,isomer #3CC(C)C(C)C(O[Si](C)(C)C(C)(C)C)C(O)C(C)C1CCC2C3COC(=O)C4CC(O)C(O[Si](C)(C)C(C)(C)C)CC4(C)C3CCC12C4342.4Semi standard non polar33892256
24-Epibrassinolide,2TBDMS,isomer #4CC(C)C(C)C(O)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C(C)(C)C)C(O)CC4(C)C3CCC12C4348.7Semi standard non polar33892256
24-Epibrassinolide,2TBDMS,isomer #5CC(C)C(C)C(O)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O)C(O[Si](C)(C)C(C)(C)C)CC4(C)C3CCC12C4334.3Semi standard non polar33892256
24-Epibrassinolide,2TBDMS,isomer #6CC(C)C(C)C(O)C(O)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)CC4(C)C3CCC12C4487.7Semi standard non polar33892256
24-Epibrassinolide,3TBDMS,isomer #1CC(C)C(C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C(C)(C)C)C(O)CC4(C)C3CCC12C4456.6Semi standard non polar33892256
24-Epibrassinolide,3TBDMS,isomer #2CC(C)C(C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O)C(O[Si](C)(C)C(C)(C)C)CC4(C)C3CCC12C4444.9Semi standard non polar33892256
24-Epibrassinolide,3TBDMS,isomer #3CC(C)C(C)C(O[Si](C)(C)C(C)(C)C)C(O)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)CC4(C)C3CCC12C4485.2Semi standard non polar33892256
24-Epibrassinolide,3TBDMS,isomer #4CC(C)C(C)C(O)C(O[Si](C)(C)C(C)(C)C)C(C)C1CCC2C3COC(=O)C4CC(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)CC4(C)C3CCC12C4478.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 24-Epibrassinolide GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-4226900000-96340cab4c372a1aedf62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 24-Epibrassinolide GC-MS (3 TMS) - 70eV, Positivesplash10-001i-3111209000-19e3d547be0a70e9894d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 24-Epibrassinolide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 24-Epibrassinolide 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 - 24-Epibrassinolide 10V, Positive-QTOFsplash10-01q9-0001900000-6023cd06ce8bedbdc2832015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Epibrassinolide 20V, Positive-QTOFsplash10-0irs-7209600000-1379db94384f19d95b252015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Epibrassinolide 40V, Positive-QTOFsplash10-0f89-9506200000-b8b41a0eea42f1c5ad042015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Epibrassinolide 10V, Negative-QTOFsplash10-004i-0001900000-0e0aa141af24536381b92015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Epibrassinolide 20V, Negative-QTOFsplash10-0200-4204900000-45aaa65683d2304275652015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Epibrassinolide 40V, Negative-QTOFsplash10-00fs-9405300000-6ab271360f13464e836a2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Epibrassinolide 10V, Negative-QTOFsplash10-004i-0000900000-3ea1694bfb516148f38a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Epibrassinolide 20V, Negative-QTOFsplash10-01t9-1202900000-a31c341a3202d435d5db2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Epibrassinolide 40V, Negative-QTOFsplash10-0ara-2007900000-794ce800cc478c075bd22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Epibrassinolide 10V, Positive-QTOFsplash10-001j-0009600000-328c8d24e38d88c962592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Epibrassinolide 20V, Positive-QTOFsplash10-00gj-2509200000-93b64b3c56e57b7837672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Epibrassinolide 40V, Positive-QTOFsplash10-0ac9-9635000000-b2f0d5cadac4d0a8b7fd2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB021012
KNApSAcK IDC00000180
Chemspider ID3126
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link24-Epibrassinolide
METLIN IDNot Available
PubChem Compound3239
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. 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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.