Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:35:51 UTC
Update Date2022-03-07 02:52:29 UTC
HMDB IDHMDB0030274
Secondary Accession Numbers
  • HMDB30274
Metabolite Identification
Common Name(E)-Casimiroedine
Description(E)-Casimiroedine belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether) (E)-Casimiroedine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on (E)-Casimiroedine.
Structure
Data?1563861963
Synonyms
ValueSource
N-[2-(1-b-D-Glucopyranosyl-1H-imidazol-4-yl)ethyl]-N-methyl-3-phenyl-2-propenamide, 9ciHMDB
Nalpha-cinnamoyl-nalpha-methylhistamine N-glucosideHMDB
Chemical FormulaC21H27N3O6
Average Molecular Weight417.4556
Monoisotopic Molecular Weight417.189985611
IUPAC Name(2E)-N-methyl-3-phenyl-N-(2-{1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1H-imidazol-4-yl}ethyl)prop-2-enamide
Traditional Namecasimiroedine
CAS Registry Number5853-02-1
SMILES
CN(CCC1=CN(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)\C=C\C1=CC=CC=C1
InChI Identifier
InChI=1S/C21H27N3O6/c1-23(17(26)8-7-14-5-3-2-4-6-14)10-9-15-11-24(13-22-15)21-20(29)19(28)18(27)16(12-25)30-21/h2-8,11,13,16,18-21,25,27-29H,9-10,12H2,1H3/b8-7+/t16-,18-,19+,20-,21-/m1/s1
InChI KeyCSFQQZOIHVWGMN-BBAXEOEJSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentGlycosylamines
Alternative Parents
Substituents
  • Cinnamic acid or derivatives
  • Hexose monosaccharide
  • N-glycosyl compound
  • Styrene
  • Monocyclic benzene moiety
  • Monosaccharide
  • N-substituted imidazole
  • Oxane
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Carboxamide group
  • Secondary alcohol
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Azacycle
  • Polyol
  • Organonitrogen compound
  • Primary alcohol
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point226.5 - 228 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility655.1 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.2 g/LALOGPS
logP0.37ALOGPS
logP-0.49ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)12.36ChemAxon
pKa (Strongest Basic)6.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area128.28 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity108.98 m³·mol⁻¹ChemAxon
Polarizability43.37 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+190.71930932474
DeepCCS[M-H]-188.82430932474
DeepCCS[M-2H]-222.06630932474
DeepCCS[M+Na]+196.41930932474
AllCCS[M+H]+202.432859911
AllCCS[M+H-H2O]+200.032859911
AllCCS[M+NH4]+204.632859911
AllCCS[M+Na]+205.232859911
AllCCS[M-H]-194.732859911
AllCCS[M+Na-2H]-195.532859911
AllCCS[M+HCOO]-196.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(E)-CasimiroedineCN(CCC1=CN(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)\C=C\C1=CC=CC=C14971.2Standard polar33892256
(E)-CasimiroedineCN(CCC1=CN(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)\C=C\C1=CC=CC=C13332.9Standard non polar33892256
(E)-CasimiroedineCN(CCC1=CN(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)\C=C\C1=CC=CC=C14141.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(E)-Casimiroedine,1TMS,isomer #1CN(CCC1=CN([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]2O)C=N1)C(=O)/C=C/C1=CC=CC=C13773.3Semi standard non polar33892256
(E)-Casimiroedine,1TMS,isomer #2CN(CCC1=CN([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O)C=N1)C(=O)/C=C/C1=CC=CC=C13725.1Semi standard non polar33892256
(E)-Casimiroedine,1TMS,isomer #3CN(CCC1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O)C=N1)C(=O)/C=C/C1=CC=CC=C13725.6Semi standard non polar33892256
(E)-Casimiroedine,1TMS,isomer #4CN(CCC1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C)C=N1)C(=O)/C=C/C1=CC=CC=C13733.9Semi standard non polar33892256
(E)-Casimiroedine,2TMS,isomer #1CN(CCC1=CN([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O)C=N1)C(=O)/C=C/C1=CC=CC=C13651.0Semi standard non polar33892256
(E)-Casimiroedine,2TMS,isomer #2CN(CCC1=CN([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O)C=N1)C(=O)/C=C/C1=CC=CC=C13666.0Semi standard non polar33892256
(E)-Casimiroedine,2TMS,isomer #3CN(CCC1=CN([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C)C=N1)C(=O)/C=C/C1=CC=CC=C13659.4Semi standard non polar33892256
(E)-Casimiroedine,2TMS,isomer #4CN(CCC1=CN([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O)C=N1)C(=O)/C=C/C1=CC=CC=C13627.2Semi standard non polar33892256
(E)-Casimiroedine,2TMS,isomer #5CN(CCC1=CN([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C)C=N1)C(=O)/C=C/C1=CC=CC=C13633.0Semi standard non polar33892256
(E)-Casimiroedine,2TMS,isomer #6CN(CCC1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=N1)C(=O)/C=C/C1=CC=CC=C13652.0Semi standard non polar33892256
(E)-Casimiroedine,3TMS,isomer #1CN(CCC1=CN([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O)C=N1)C(=O)/C=C/C1=CC=CC=C13629.5Semi standard non polar33892256
(E)-Casimiroedine,3TMS,isomer #2CN(CCC1=CN([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C)C=N1)C(=O)/C=C/C1=CC=CC=C13615.6Semi standard non polar33892256
(E)-Casimiroedine,3TMS,isomer #3CN(CCC1=CN([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=N1)C(=O)/C=C/C1=CC=CC=C13634.7Semi standard non polar33892256
(E)-Casimiroedine,3TMS,isomer #4CN(CCC1=CN([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=N1)C(=O)/C=C/C1=CC=CC=C13617.5Semi standard non polar33892256
(E)-Casimiroedine,4TMS,isomer #1CN(CCC1=CN([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=N1)C(=O)/C=C/C1=CC=CC=C13640.5Semi standard non polar33892256
(E)-Casimiroedine,1TBDMS,isomer #1CN(CCC1=CN([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]2O)C=N1)C(=O)/C=C/C1=CC=CC=C14009.3Semi standard non polar33892256
(E)-Casimiroedine,1TBDMS,isomer #2CN(CCC1=CN([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O)C=N1)C(=O)/C=C/C1=CC=CC=C13959.6Semi standard non polar33892256
(E)-Casimiroedine,1TBDMS,isomer #3CN(CCC1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=N1)C(=O)/C=C/C1=CC=CC=C13975.6Semi standard non polar33892256
(E)-Casimiroedine,1TBDMS,isomer #4CN(CCC1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1)C(=O)/C=C/C1=CC=CC=C13973.7Semi standard non polar33892256
(E)-Casimiroedine,2TBDMS,isomer #1CN(CCC1=CN([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O)C=N1)C(=O)/C=C/C1=CC=CC=C14081.6Semi standard non polar33892256
(E)-Casimiroedine,2TBDMS,isomer #2CN(CCC1=CN([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=N1)C(=O)/C=C/C1=CC=CC=C14104.9Semi standard non polar33892256
(E)-Casimiroedine,2TBDMS,isomer #3CN(CCC1=CN([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1)C(=O)/C=C/C1=CC=CC=C14097.0Semi standard non polar33892256
(E)-Casimiroedine,2TBDMS,isomer #4CN(CCC1=CN([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=N1)C(=O)/C=C/C1=CC=CC=C14064.6Semi standard non polar33892256
(E)-Casimiroedine,2TBDMS,isomer #5CN(CCC1=CN([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1)C(=O)/C=C/C1=CC=CC=C14070.4Semi standard non polar33892256
(E)-Casimiroedine,2TBDMS,isomer #6CN(CCC1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1)C(=O)/C=C/C1=CC=CC=C14086.0Semi standard non polar33892256
(E)-Casimiroedine,3TBDMS,isomer #1CN(CCC1=CN([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=N1)C(=O)/C=C/C1=CC=CC=C14211.4Semi standard non polar33892256
(E)-Casimiroedine,3TBDMS,isomer #2CN(CCC1=CN([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1)C(=O)/C=C/C1=CC=CC=C14214.0Semi standard non polar33892256
(E)-Casimiroedine,3TBDMS,isomer #3CN(CCC1=CN([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1)C(=O)/C=C/C1=CC=CC=C14219.8Semi standard non polar33892256
(E)-Casimiroedine,3TBDMS,isomer #4CN(CCC1=CN([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1)C(=O)/C=C/C1=CC=CC=C14185.1Semi standard non polar33892256
(E)-Casimiroedine,4TBDMS,isomer #1CN(CCC1=CN([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=N1)C(=O)/C=C/C1=CC=CC=C14387.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (E)-Casimiroedine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kn9-6928100000-887191331405f5c3749c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (E)-Casimiroedine GC-MS (3 TMS) - 70eV, Positivesplash10-0159-3862139000-e541ba9b876745fef8ce2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (E)-Casimiroedine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (E)-Casimiroedine 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 - (E)-Casimiroedine 10V, Positive-QTOFsplash10-0aor-0490400000-5cd3f63e36021895f3742016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-Casimiroedine 20V, Positive-QTOFsplash10-00di-1930000000-9c630e10ad6e0420cf5e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-Casimiroedine 40V, Positive-QTOFsplash10-00di-3920000000-5d588d08c77b8cc4f4762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-Casimiroedine 10V, Negative-QTOFsplash10-0gb9-0174900000-88d9e83302933d604da22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-Casimiroedine 20V, Negative-QTOFsplash10-0udi-0292000000-b7f49e884739f9c6c9fb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-Casimiroedine 40V, Negative-QTOFsplash10-0ik9-5930000000-903043bf9aac763475c52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-Casimiroedine 10V, Negative-QTOFsplash10-014i-0010900000-7e8a5503384890b4cf382021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-Casimiroedine 20V, Negative-QTOFsplash10-0udi-2092000000-d0179a09c1d6ceb08fb02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-Casimiroedine 40V, Negative-QTOFsplash10-0w29-3930400000-24bea8a5d42275e7e0882021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-Casimiroedine 10V, Positive-QTOFsplash10-014i-0020900000-4b7941f1da161279352e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-Casimiroedine 20V, Positive-QTOFsplash10-0zfr-1984500000-8073d9ccaa5e1c9cacf02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (E)-Casimiroedine 40V, Positive-QTOFsplash10-0pi1-3891000000-b82c3e0dc2d4eae9c0792021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart 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 IDFDB002106
KNApSAcK IDC00002321
Chemspider ID4445129
KEGG Compound IDC10577
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281818
PDB IDNot Available
ChEBI ID3451
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1818611
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .