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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:02:17 UTC
Update Date2022-03-07 02:54:43 UTC
HMDB IDHMDB0035979
Secondary Accession Numbers
  • HMDB35979
Metabolite Identification
Common NameCyclobranol
Description(S)-Spirobrassinin belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole (S)-Spirobrassinin is a strong basic compound (based on its pKa). Outside of the human body, (S)-Spirobrassinin has been detected, but not quantified in, a few different foods, such as cauliflowers, chinese cabbages, and radish. This could make (S)-spirobrassinin a potential biomarker for the consumption of these foods.
Structure
Data?1563862802
Synonyms
ValueSource
Cyclobranol (24-methylcycloartenol) acetateHMDB
Chemical FormulaC31H52O
Average Molecular Weight440.744
Monoisotopic Molecular Weight440.401816286
IUPAC Name15-(5,6-dimethylhept-5-en-2-yl)-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-ol
Traditional Name15-(5,6-dimethylhept-5-en-2-yl)-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-ol
CAS Registry Number25692-13-1
SMILES
CC(CCC(C)=C(C)C)C1CCC2(C)C3CCC4C5(CC35CCC12C)CCC(O)C4(C)C
InChI Identifier
InChI=1S/C31H52O/c1-20(2)21(3)9-10-22(4)23-13-15-29(8)25-12-11-24-27(5,6)26(32)14-16-30(24)19-31(25,30)18-17-28(23,29)7/h22-26,32H,9-19H2,1-8H3
InChI KeyCIBNJPPYSPYHDB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolines
Direct ParentIndolines
Alternative Parents
Substituents
  • Dihydroindole
  • Benzenoid
  • Meta-thiazoline
  • Carboxamide group
  • Lactam
  • Secondary carboxylic acid amide
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Carboxylic acid derivative
  • Azacycle
  • Organopnictogen compound
  • Organic oxygen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point156.5 - 157.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00012 g/LALOGPS
logP6.4ALOGPS
logP7.79ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)19.49ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity136.32 m³·mol⁻¹ChemAxon
Polarizability56.87 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+204.90131661259
DarkChem[M-H]-198.13631661259
DeepCCS[M-2H]-253.6430932474
DeepCCS[M+Na]+228.86830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CyclobranolCC(CCC(C)=C(C)C)C1CCC2(C)C3CCC4C5(CC35CCC12C)CCC(O)C4(C)C2762.4Standard polar33892256
CyclobranolCC(CCC(C)=C(C)C)C1CCC2(C)C3CCC4C5(CC35CCC12C)CCC(O)C4(C)C3411.4Standard non polar33892256
CyclobranolCC(CCC(C)=C(C)C)C1CCC2(C)C3CCC4C5(CC35CCC12C)CCC(O)C4(C)C3529.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cyclobranol,1TMS,isomer #1CC(C)=C(C)CCC(C)C1CCC2(C)C3CCC4C(C)(C)C(O[Si](C)(C)C)CCC45CC35CCC12C3553.6Semi standard non polar33892256
Cyclobranol,1TBDMS,isomer #1CC(C)=C(C)CCC(C)C1CCC2(C)C3CCC4C(C)(C)C(O[Si](C)(C)C(C)(C)C)CCC45CC35CCC12C3773.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cyclobranol GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-4124900000-ef48c3038e2e95e5c5f62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclobranol GC-MS (1 TMS) - 70eV, Positivesplash10-000t-5011900000-f3fd513e3cc1c47a95c22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclobranol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclobranol 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 - Cyclobranol 10V, Positive-QTOFsplash10-00dl-1004900000-8235ce5837bf510372ef2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclobranol 20V, Positive-QTOFsplash10-001i-4019300000-aa3e390389e5806af8ca2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclobranol 40V, Positive-QTOFsplash10-001i-9176200000-df6f0e7ddeab81f1bdd22016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclobranol 10V, Negative-QTOFsplash10-000i-0000900000-f38bb8c73bac310258ff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclobranol 20V, Negative-QTOFsplash10-000i-0000900000-2531bf3c1bf1a9a27e9b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclobranol 40V, Negative-QTOFsplash10-05fr-2004900000-cd149b69075b269ad8882016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclobranol 10V, Negative-QTOFsplash10-000i-0000900000-6abf4200d93b5ca719d02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclobranol 20V, Negative-QTOFsplash10-000i-0000900000-6abf4200d93b5ca719d02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclobranol 40V, Negative-QTOFsplash10-000i-0001900000-59ed6e3c026bb9a4e61f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclobranol 10V, Positive-QTOFsplash10-00lv-9107200000-5cbfcfc5d8851548572e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclobranol 20V, Positive-QTOFsplash10-05o0-9102100000-1d47f40f2e09aa8737772021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclobranol 40V, Positive-QTOFsplash10-001l-9221000000-4109ab4c7634fd66f1ea2021-09-24Wishart 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 IDFDB011345
KNApSAcK IDNot Available
Chemspider ID4930317
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6424827
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.