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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 14:44:39 UTC
Update Date2021-09-26 23:09:46 UTC
HMDB IDHMDB0255167
Secondary Accession NumbersNone
Metabolite Identification
Common Namen-methacryloyl-l-histidine methyl ester
Descriptionn-methacryloyl-l-histidine methyl ester belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Based on a literature review a significant number of articles have been published on n-methacryloyl-l-histidine methyl ester. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-methacryloyl-l-histidine methyl ester is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically n-methacryloyl-l-histidine methyl ester is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC11H15N3O3
Average Molecular Weight237.259
Monoisotopic Molecular Weight237.111341355
IUPAC Namemethyl 3-(1H-imidazol-5-yl)-2-(2-methylprop-2-enamido)propanoate
Traditional Namemethyl 3-(3H-imidazol-4-yl)-2-(2-methylprop-2-enamido)propanoate
CAS Registry NumberNot Available
SMILES
COC(=O)C(CC1=CN=CN1)NC(=O)C(C)=C
InChI Identifier
InChI=1S/C11H15N3O3/c1-7(2)10(15)14-9(11(16)17-3)4-8-5-12-6-13-8/h5-6,9H,1,4H2,2-3H3,(H,12,13)(H,14,15)
InChI KeyLTELWGJDCBOKRL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentHistidine and derivatives
Alternative Parents
Substituents
  • Histidine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid ester
  • Imidazolyl carboxylic acid derivative
  • Fatty acid ester
  • Fatty acyl
  • Heteroaromatic compound
  • Methyl ester
  • Imidazole
  • Azole
  • Secondary carboxylic acid amide
  • Carboxylic acid ester
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
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
logP0.07ALOGPS
logP-0.23ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)12.41ChemAxon
pKa (Strongest Basic)6.74ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area84.08 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity61.28 m³·mol⁻¹ChemAxon
Polarizability23.95 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+154.1330932474
DeepCCS[M-H]-151.77230932474
DeepCCS[M-2H]-184.71330932474
DeepCCS[M+Na]+160.22330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
n-methacryloyl-l-histidine methyl esterCOC(=O)C(CC1=CN=CN1)NC(=O)C(C)=C2658.6Standard polar33892256
n-methacryloyl-l-histidine methyl esterCOC(=O)C(CC1=CN=CN1)NC(=O)C(C)=C1386.1Standard non polar33892256
n-methacryloyl-l-histidine methyl esterCOC(=O)C(CC1=CN=CN1)NC(=O)C(C)=C2140.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
n-methacryloyl-l-histidine methyl ester,1TMS,isomer #1C=C(C)C(=O)NC(CC1=CN=CN1[Si](C)(C)C)C(=O)OC2172.6Semi standard non polar33892256
n-methacryloyl-l-histidine methyl ester,1TMS,isomer #1C=C(C)C(=O)NC(CC1=CN=CN1[Si](C)(C)C)C(=O)OC1964.3Standard non polar33892256
n-methacryloyl-l-histidine methyl ester,1TMS,isomer #1C=C(C)C(=O)NC(CC1=CN=CN1[Si](C)(C)C)C(=O)OC3047.2Standard polar33892256
n-methacryloyl-l-histidine methyl ester,1TMS,isomer #2C=C(C)C(=O)N(C(CC1=CN=C[NH]1)C(=O)OC)[Si](C)(C)C1993.9Semi standard non polar33892256
n-methacryloyl-l-histidine methyl ester,1TMS,isomer #2C=C(C)C(=O)N(C(CC1=CN=C[NH]1)C(=O)OC)[Si](C)(C)C1990.1Standard non polar33892256
n-methacryloyl-l-histidine methyl ester,1TMS,isomer #2C=C(C)C(=O)N(C(CC1=CN=C[NH]1)C(=O)OC)[Si](C)(C)C2899.0Standard polar33892256
n-methacryloyl-l-histidine methyl ester,2TMS,isomer #1C=C(C)C(=O)N(C(CC1=CN=CN1[Si](C)(C)C)C(=O)OC)[Si](C)(C)C2143.3Semi standard non polar33892256
n-methacryloyl-l-histidine methyl ester,2TMS,isomer #1C=C(C)C(=O)N(C(CC1=CN=CN1[Si](C)(C)C)C(=O)OC)[Si](C)(C)C2053.3Standard non polar33892256
n-methacryloyl-l-histidine methyl ester,2TMS,isomer #1C=C(C)C(=O)N(C(CC1=CN=CN1[Si](C)(C)C)C(=O)OC)[Si](C)(C)C2672.1Standard polar33892256
n-methacryloyl-l-histidine methyl ester,1TBDMS,isomer #1C=C(C)C(=O)NC(CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)OC2396.2Semi standard non polar33892256
n-methacryloyl-l-histidine methyl ester,1TBDMS,isomer #1C=C(C)C(=O)NC(CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)OC2163.3Standard non polar33892256
n-methacryloyl-l-histidine methyl ester,1TBDMS,isomer #1C=C(C)C(=O)NC(CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)OC3072.4Standard polar33892256
n-methacryloyl-l-histidine methyl ester,1TBDMS,isomer #2C=C(C)C(=O)N(C(CC1=CN=C[NH]1)C(=O)OC)[Si](C)(C)C(C)(C)C2231.6Semi standard non polar33892256
n-methacryloyl-l-histidine methyl ester,1TBDMS,isomer #2C=C(C)C(=O)N(C(CC1=CN=C[NH]1)C(=O)OC)[Si](C)(C)C(C)(C)C2227.2Standard non polar33892256
n-methacryloyl-l-histidine methyl ester,1TBDMS,isomer #2C=C(C)C(=O)N(C(CC1=CN=C[NH]1)C(=O)OC)[Si](C)(C)C(C)(C)C2964.4Standard polar33892256
n-methacryloyl-l-histidine methyl ester,2TBDMS,isomer #1C=C(C)C(=O)N(C(CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)OC)[Si](C)(C)C(C)(C)C2581.7Semi standard non polar33892256
n-methacryloyl-l-histidine methyl ester,2TBDMS,isomer #1C=C(C)C(=O)N(C(CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)OC)[Si](C)(C)C(C)(C)C2462.7Standard non polar33892256
n-methacryloyl-l-histidine methyl ester,2TBDMS,isomer #1C=C(C)C(=O)N(C(CC1=CN=CN1[Si](C)(C)C(C)(C)C)C(=O)OC)[Si](C)(C)C(C)(C)C2797.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - n-methacryloyl-l-histidine methyl ester GC-MS (Non-derivatized) - 70eV, Positivesplash10-00or-9510000000-65f8c2d13251181f02502021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - n-methacryloyl-l-histidine methyl ester GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-10-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound86021246
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]