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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:52:01 UTC
Update Date2022-03-07 02:53:58 UTC
HMDB IDHMDB0034081
Secondary Accession Numbers
  • HMDB34081
Metabolite Identification
Common NameBrassinolide
DescriptionBrassinolide 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. Thus, brassinolide is considered to be a sterol. Based on a literature review a significant number of articles have been published on Brassinolide.
Structure
Data?1563862507
Synonyms
ValueSource
24-EpibrassinolideChEMBL, HMDB
2,3,22,23-Tetrahydroxy-24-methyl-b-homo-7-oxacholestan-6-oneHMDB
2alpha,3alpha,22alpha,23alpha-Tetrahydroxy-24alpha-methyl-b-homo-7-oxa-5alpha-cholestan-6-oneMeSH, HMDB
Brassinolide, (2alpha,3alpha,5alpha,22S,23S)-isomerMeSH, HMDB
Brassinolide, (2alpha,3alpha,5alpha.22R,23R)-isomerMeSH, HMDB
BrassinolideMeSH
Chemical FormulaC28H48O6
Average Molecular Weight480.6771
Monoisotopic Molecular Weight480.345089268
IUPAC Name(1S,2R,4R,5S,7S,11S,12S,15R,16S)-15-[(2S,3R,4R,5R)-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 Name24-epi-brassinolide
CAS Registry Number72962-43-7
SMILES
[H][C@@]12CC[C@H]([C@H](C)[C@@H](O)[C@H](O)[C@H](C)C(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])COC(=O)[C@@]2([H])C[C@H](O)[C@H](O)C[C@]12C
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/t15-,16+,17+,18-,19+,20+,21-,22+,23-,24-,25-,27-,28-/m1/s1
InChI KeyIXVMHGVQKLDRKH-QHBHMFGVSA-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
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point274 - 275 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility6.53 mg/L @ 25 °C (est)The Good Scents Company Information System
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
Polarizability55.6 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
DeepCCS[M-2H]-244.78230932474
DeepCCS[M+Na]+219.70730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Brassinolide[H][C@@]12CC[C@H]([C@H](C)[C@@H](O)[C@H](O)[C@H](C)C(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])COC(=O)[C@@]2([H])C[C@H](O)[C@H](O)C[C@]12C3442.1Standard polar33892256
Brassinolide[H][C@@]12CC[C@H]([C@H](C)[C@@H](O)[C@H](O)[C@H](C)C(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])COC(=O)[C@@]2([H])C[C@H](O)[C@H](O)C[C@]12C3681.4Standard non polar33892256
Brassinolide[H][C@@]12CC[C@H]([C@H](C)[C@@H](O)[C@H](O)[C@H](C)C(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])COC(=O)[C@@]2([H])C[C@H](O)[C@H](O)C[C@]12C3999.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Brassinolide,1TMS,isomer #1CC(C)[C@@H](C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O)[C@H](O)C[C@]4(C)[C@H]3CC[C@@]21C3738.3Semi standard non polar33892256
Brassinolide,1TMS,isomer #2CC(C)[C@@H](C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O)[C@H](O)C[C@]4(C)[C@H]3CC[C@@]21C3722.0Semi standard non polar33892256
Brassinolide,1TMS,isomer #3CC(C)[C@@H](C)[C@@H](O)[C@H](O)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O[Si](C)(C)C)[C@H](O)C[C@]4(C)[C@H]3CC[C@@]21C3751.4Semi standard non polar33892256
Brassinolide,1TMS,isomer #4CC(C)[C@@H](C)[C@@H](O)[C@H](O)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O)[C@H](O[Si](C)(C)C)C[C@]4(C)[C@H]3CC[C@@]21C3783.8Semi standard non polar33892256
Brassinolide,2TMS,isomer #1CC(C)[C@@H](C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O)[C@H](O)C[C@]4(C)[C@H]3CC[C@@]21C3639.8Semi standard non polar33892256
Brassinolide,2TMS,isomer #2CC(C)[C@@H](C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O[Si](C)(C)C)[C@H](O)C[C@]4(C)[C@H]3CC[C@@]21C3671.5Semi standard non polar33892256
Brassinolide,2TMS,isomer #3CC(C)[C@@H](C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O)[C@H](O[Si](C)(C)C)C[C@]4(C)[C@H]3CC[C@@]21C3702.0Semi standard non polar33892256
Brassinolide,2TMS,isomer #4CC(C)[C@@H](C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O[Si](C)(C)C)[C@H](O)C[C@]4(C)[C@H]3CC[C@@]21C3646.2Semi standard non polar33892256
Brassinolide,2TMS,isomer #5CC(C)[C@@H](C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O)[C@H](O[Si](C)(C)C)C[C@]4(C)[C@H]3CC[C@@]21C3673.8Semi standard non polar33892256
Brassinolide,2TMS,isomer #6CC(C)[C@@H](C)[C@@H](O)[C@H](O)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C[C@]4(C)[C@H]3CC[C@@]21C3671.4Semi standard non polar33892256
Brassinolide,3TMS,isomer #1CC(C)[C@@H](C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O[Si](C)(C)C)[C@H](O)C[C@]4(C)[C@H]3CC[C@@]21C3626.8Semi standard non polar33892256
Brassinolide,3TMS,isomer #2CC(C)[C@@H](C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O)[C@H](O[Si](C)(C)C)C[C@]4(C)[C@H]3CC[C@@]21C3656.6Semi standard non polar33892256
Brassinolide,3TMS,isomer #3CC(C)[C@@H](C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C[C@]4(C)[C@H]3CC[C@@]21C3650.0Semi standard non polar33892256
Brassinolide,3TMS,isomer #4CC(C)[C@@H](C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C[C@]4(C)[C@H]3CC[C@@]21C3620.7Semi standard non polar33892256
Brassinolide,4TMS,isomer #1CC(C)[C@@H](C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C[C@]4(C)[C@H]3CC[C@@]21C3633.9Semi standard non polar33892256
Brassinolide,1TBDMS,isomer #1CC(C)[C@@H](C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O)[C@H](O)C[C@]4(C)[C@H]3CC[C@@]21C3977.7Semi standard non polar33892256
Brassinolide,1TBDMS,isomer #2CC(C)[C@@H](C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O)[C@H](O)C[C@]4(C)[C@H]3CC[C@@]21C3963.0Semi standard non polar33892256
Brassinolide,1TBDMS,isomer #3CC(C)[C@@H](C)[C@@H](O)[C@H](O)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C[C@]4(C)[C@H]3CC[C@@]21C3964.4Semi standard non polar33892256
Brassinolide,1TBDMS,isomer #4CC(C)[C@@H](C)[C@@H](O)[C@H](O)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C[C@]4(C)[C@H]3CC[C@@]21C3999.5Semi standard non polar33892256
Brassinolide,2TBDMS,isomer #1CC(C)[C@@H](C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O)[C@H](O)C[C@]4(C)[C@H]3CC[C@@]21C4138.3Semi standard non polar33892256
Brassinolide,2TBDMS,isomer #2CC(C)[C@@H](C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C[C@]4(C)[C@H]3CC[C@@]21C4123.9Semi standard non polar33892256
Brassinolide,2TBDMS,isomer #3CC(C)[C@@H](C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C[C@]4(C)[C@H]3CC[C@@]21C4153.3Semi standard non polar33892256
Brassinolide,2TBDMS,isomer #4CC(C)[C@@H](C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C[C@]4(C)[C@H]3CC[C@@]21C4099.2Semi standard non polar33892256
Brassinolide,2TBDMS,isomer #5CC(C)[C@@H](C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C[C@]4(C)[C@H]3CC[C@@]21C4129.4Semi standard non polar33892256
Brassinolide,2TBDMS,isomer #6CC(C)[C@@H](C)[C@@H](O)[C@H](O)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C[C@]4(C)[C@H]3CC[C@@]21C4100.3Semi standard non polar33892256
Brassinolide,3TBDMS,isomer #1CC(C)[C@@H](C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C[C@]4(C)[C@H]3CC[C@@]21C4308.4Semi standard non polar33892256
Brassinolide,3TBDMS,isomer #2CC(C)[C@@H](C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C[C@]4(C)[C@H]3CC[C@@]21C4333.1Semi standard non polar33892256
Brassinolide,3TBDMS,isomer #3CC(C)[C@@H](C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C[C@]4(C)[C@H]3CC[C@@]21C4295.7Semi standard non polar33892256
Brassinolide,3TBDMS,isomer #4CC(C)[C@@H](C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3COC(=O)[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C[C@]4(C)[C@H]3CC[C@@]21C4267.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Brassinolide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ir3-4315900000-c0cdd9a5e00ed559b0372017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Brassinolide GC-MS (3 TMS) - 70eV, Positivesplash10-001i-3111209000-19e3d547be0a70e9894d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Brassinolide 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 - Brassinolide 10V, Positive-QTOFsplash10-01q9-0001900000-f751356e978d7611841d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassinolide 20V, Positive-QTOFsplash10-0irs-7209600000-b9396588d263ce2fe7e32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassinolide 40V, Positive-QTOFsplash10-0f89-9506200000-0d91d1fed47d6d5f72cf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassinolide 10V, Negative-QTOFsplash10-004i-0000900000-52b84cac64a5ac86adbf2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassinolide 20V, Negative-QTOFsplash10-0200-3204900000-88c87f58b6d8d294c7902016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassinolide 40V, Negative-QTOFsplash10-00fs-9405300000-065785cd0b58a99795452016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassinolide 10V, Negative-QTOFsplash10-004i-0000900000-b27078fda0520f837b352021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassinolide 20V, Negative-QTOFsplash10-004j-2305900000-f2b2e8bcfa7706e2375d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassinolide 40V, Negative-QTOFsplash10-056r-3005900000-b530898f59fc290c09512021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassinolide 10V, Positive-QTOFsplash10-001j-0009600000-c36102c0fe9ca31dc76b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassinolide 20V, Positive-QTOFsplash10-008a-4309100000-2ca728d9dc9e0fbfb8092021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassinolide 40V, Positive-QTOFsplash10-0a4l-9415000000-36c9809f108ce77f93642021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 IDFDB012340
KNApSAcK IDC00000180
Chemspider ID391354
KEGG Compound IDC11049
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBrassinolide
METLIN IDNot Available
PubChem Compound443055
PDB IDNot Available
ChEBI ID27722
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1588611
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.