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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:29:35 UTC
Update Date2021-09-14 15:47:07 UTC
HMDB IDHMDB0039126
Secondary Accession Numbers
  • HMDB39126
Metabolite Identification
Common NameWybutoxine
DescriptionWybutoxine belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. Based on a literature review very few articles have been published on Wybutoxine.
Structure
Data?1563863318
Synonyms
ValueSource
Methyl 4,9-dihydro-b-hydroperoxy-a-[(methoxycarbonyl)amino]-4,6-dimethyl-9-oxo-1H-imidazo[1,2-a]purine-7-butanoate, 9ciHMDB
Peroxy-y-baseHMDB
PeroxywybutineHMDB
Methyl 4-{4,6-dimethyl-9-oxo-3H,4H,9H-imidazo[1,2-a]purin-7-yl}-3-hydroperoxy-2-{[hydroxy(methoxy)methylidene]amino}butanoic acidGenerator
Chemical FormulaC16H20N6O7
Average Molecular Weight408.366
Monoisotopic Molecular Weight408.139347024
IUPAC Namemethyl 4-{4,6-dimethyl-9-oxo-1H,4H,9H-imidazo[1,2-a]purin-7-yl}-3-hydroperoxy-2-[(methoxycarbonyl)amino]butanoate
Traditional Namemethyl 4-{4,6-dimethyl-9-oxo-1H-imidazo[1,2-a]purin-7-yl}-3-hydroperoxy-2-[(methoxycarbonyl)amino]butanoate
CAS Registry Number36238-44-5
SMILES
COC(=O)NC(C(CC1=C(C)N=C2N1C(=O)C1=C(N=CN1)N2C)OO)C(=O)OC
InChI Identifier
InChI=1S/C16H20N6O7/c1-7-8(5-9(29-26)10(14(24)27-3)20-16(25)28-4)22-13(23)11-12(18-6-17-11)21(2)15(22)19-7/h6,9-10,26H,5H2,1-4H3,(H,17,18)(H,20,25)
InChI KeyFRYWGCQTDZARGT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid esters
Alternative Parents
Substituents
  • Alpha-amino acid ester
  • 6-oxopurine
  • Hypoxanthine
  • Imidazopyrimidine
  • Purine
  • Imidazo[1,2-a]pyrimidine
  • Pyrimidone
  • Fatty acid ester
  • N-substituted imidazole
  • Fatty acyl
  • Pyrimidine
  • Methylcarbamate
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Vinylogous amide
  • Methyl ester
  • Carbamic acid ester
  • Lactam
  • Carbonic acid derivative
  • Hydroperoxide
  • Carboxylic acid ester
  • Alkyl hydroperoxide
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Peroxol
  • Organic oxide
  • Organonitrogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.6 g/LALOGPS
logP10(0.55) g/LALOGPS
logP10(-0.87) g/LChemAxon
logS10(-2.2) g/LALOGPS
pKa (Strongest Acidic)10.37ChemAxon
pKa (Strongest Basic)0.51ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area160.9 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity95.68 m³·mol⁻¹ChemAxon
Polarizability39.64 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
DarkChem[M+H]+195.77131661259
DarkChem[M-H]-188.52631661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
WybutoxineCOC(=O)NC(C(CC1=C(C)N=C2N1C(=O)C1=C(N=CN1)N2C)OO)C(=O)OC3809.4Standard polar33892256
WybutoxineCOC(=O)NC(C(CC1=C(C)N=C2N1C(=O)C1=C(N=CN1)N2C)OO)C(=O)OC2747.9Standard non polar33892256
WybutoxineCOC(=O)NC(C(CC1=C(C)N=C2N1C(=O)C1=C(N=CN1)N2C)OO)C(=O)OC3549.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Wybutoxine,1TMS,isomer #1COC(=O)C(C(CC1=C(C)N=C2N(C)C3=C([NH]C=N3)C(=O)N12)OO)N(C(=O)OC)[Si](C)(C)C3336.2Semi standard non polar33892256
Wybutoxine,1TMS,isomer #1COC(=O)C(C(CC1=C(C)N=C2N(C)C3=C([NH]C=N3)C(=O)N12)OO)N(C(=O)OC)[Si](C)(C)C3157.5Standard non polar33892256
Wybutoxine,1TMS,isomer #2COC(=O)NC(C(=O)OC)C(CC1=C(C)N=C2N(C)C3=C(C(=O)N12)N([Si](C)(C)C)C=N3)OO3395.2Semi standard non polar33892256
Wybutoxine,1TMS,isomer #2COC(=O)NC(C(=O)OC)C(CC1=C(C)N=C2N(C)C3=C(C(=O)N12)N([Si](C)(C)C)C=N3)OO3139.6Standard non polar33892256
Wybutoxine,2TMS,isomer #1COC(=O)C(C(CC1=C(C)N=C2N(C)C3=C(C(=O)N12)N([Si](C)(C)C)C=N3)OO)N(C(=O)OC)[Si](C)(C)C3304.7Semi standard non polar33892256
Wybutoxine,2TMS,isomer #1COC(=O)C(C(CC1=C(C)N=C2N(C)C3=C(C(=O)N12)N([Si](C)(C)C)C=N3)OO)N(C(=O)OC)[Si](C)(C)C3147.3Standard non polar33892256
Wybutoxine,1TBDMS,isomer #1COC(=O)C(C(CC1=C(C)N=C2N(C)C3=C([NH]C=N3)C(=O)N12)OO)N(C(=O)OC)[Si](C)(C)C(C)(C)C3531.0Semi standard non polar33892256
Wybutoxine,1TBDMS,isomer #1COC(=O)C(C(CC1=C(C)N=C2N(C)C3=C([NH]C=N3)C(=O)N12)OO)N(C(=O)OC)[Si](C)(C)C(C)(C)C3332.0Standard non polar33892256
Wybutoxine,1TBDMS,isomer #2COC(=O)NC(C(=O)OC)C(CC1=C(C)N=C2N(C)C3=C(C(=O)N12)N([Si](C)(C)C(C)(C)C)C=N3)OO3591.9Semi standard non polar33892256
Wybutoxine,1TBDMS,isomer #2COC(=O)NC(C(=O)OC)C(CC1=C(C)N=C2N(C)C3=C(C(=O)N12)N([Si](C)(C)C(C)(C)C)C=N3)OO3329.5Standard non polar33892256
Wybutoxine,2TBDMS,isomer #1COC(=O)C(C(CC1=C(C)N=C2N(C)C3=C(C(=O)N12)N([Si](C)(C)C(C)(C)C)C=N3)OO)N(C(=O)OC)[Si](C)(C)C(C)(C)C3709.1Semi standard non polar33892256
Wybutoxine,2TBDMS,isomer #1COC(=O)C(C(CC1=C(C)N=C2N(C)C3=C(C(=O)N12)N([Si](C)(C)C(C)(C)C)C=N3)OO)N(C(=O)OC)[Si](C)(C)C(C)(C)C3528.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Wybutoxine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0092-8549000000-e95459cdd2a46f8d98272017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Wybutoxine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Wybutoxine 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 - Wybutoxine 10V, Positive-QTOFsplash10-0a6r-0109700000-42cd526479b05f760baf2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Wybutoxine 20V, Positive-QTOFsplash10-004i-0009000000-6be65d5ffdb842c39ae92015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Wybutoxine 40V, Positive-QTOFsplash10-01bj-9452000000-b3f885328291dff5a80f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Wybutoxine 10V, Negative-QTOFsplash10-056r-0009300000-e0e5e86cbd130b0b112e2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Wybutoxine 20V, Negative-QTOFsplash10-01r5-3329100000-7b31bc961f78ffff57f52015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Wybutoxine 40V, Negative-QTOFsplash10-0006-9203000000-b6c6c4b5a7a7649f3dd72015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Wybutoxine 10V, Positive-QTOFsplash10-0006-0098300000-1ac127cc4a33497a10002021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Wybutoxine 20V, Positive-QTOFsplash10-014i-1189000000-d4e73b46a3c7ebe78d272021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Wybutoxine 40V, Positive-QTOFsplash10-014i-6896000000-d7c1cf0b191abdd8d1922021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Wybutoxine 10V, Negative-QTOFsplash10-0uxu-5429100000-681578a6e3cea0de9fff2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Wybutoxine 20V, Negative-QTOFsplash10-00kf-2089000000-a2419c1466bc3b8f91372021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Wybutoxine 40V, Negative-QTOFsplash10-0006-6195000000-1d178466438140b005252021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart 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 IDFDB018638
KNApSAcK IDNot Available
Chemspider ID167683
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound193232
PDB IDNot Available
ChEBI ID165847
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .