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Brassinolide (FDB012340)

Record Information
Version1.0
Creation date2010-04-08 22:10:07 UTC
Update date2019-11-26 03:06:36 UTC
Primary IDFDB012340
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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.
CAS Number72962-43-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted 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
Chemical FormulaC28H48O6
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
InChI IdentifierInChI=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
Isomeric 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
Average Molecular Weight480.6771
Monoisotopic Molecular Weight480.345089268
Classification
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

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 69.96%; H 10.06%; O 19.97%DFC
Melting PointMp 274-275°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]24D +41.9 (CHCl3/MeOH, 9:1)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSBrassinolide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ir3-4315900000-c0cdd9a5e00ed559b037Spectrum
Predicted GC-MSBrassinolide, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-3111209000-19e3d547be0a70e9894dSpectrum
Predicted GC-MSBrassinolide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0001900000-f751356e978d7611841d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0irs-7209600000-b9396588d263ce2fe7e32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-9506200000-0d91d1fed47d6d5f72cf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-52b84cac64a5ac86adbf2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0200-3204900000-88c87f58b6d8d294c7902016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fs-9405300000-065785cd0b58a99795452016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-b27078fda0520f837b352021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-2305900000-f2b2e8bcfa7706e2375d2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-3005900000-b530898f59fc290c09512021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0009600000-c36102c0fe9ca31dc76b2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-008a-4309100000-2ca728d9dc9e0fbfb8092021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9415000000-36c9809f108ce77f93642021-09-25View Spectrum
NMRNot Available
ChemSpider ID391354
ChEMBL IDCHEMBL563853
KEGG Compound IDC11049
Pubchem Compound ID443055
Pubchem Substance IDNot Available
ChEBI ID28277
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34081
CRC / DFC (Dictionary of Food Compounds) IDHGL01-Q:HGL01-Q
EAFUS IDNot Available
Dr. Duke IDBRASSINOLIDE
BIGG IDNot Available
KNApSAcK IDC00000176
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDBrassinolide
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
juvabionalDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
phytohormonal26158 A plant growth regulator that modulates the formation of stems, leaves and flowers, as well as the development and ripening of fruit. The term includes endogenous and non-endogenous compounds (e.g. active compounds produced by bacteria on the leaf surface) as well as semi-synthetic and fully synthetic compounds.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).