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Record Information
Version1.0
Created at2022-09-05 18:07:51 UTC
Updated at2022-09-05 18:07:51 UTC
NP-MRD IDNP0217701
Secondary Accession NumbersNone
Natural Product Identification
Common Namehistidine methyl ester
DescriptionHistidine methyl ester, also known as methyl histidinate, 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. Histidine methyl ester is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. It was first documented in 2017 (PMID: 28625064). Based on a literature review a significant number of articles have been published on histidine methyl ester (PMID: 35884285) (PMID: 35743851) (PMID: 35683095) (PMID: 34472144) (PMID: 34410672) (PMID: 33961908).
Structure
Thumb
Synonyms
ValueSource
Methyl histidinateChEBI
Methyl histidinic acidGenerator
Chemical FormulaC7H11N3O2
Average Mass169.1840 Da
Monoisotopic Mass169.08513 Da
IUPAC Namemethyl 2-amino-3-(1H-imidazol-5-yl)propanoate
Traditional Namemethyl 2-amino-3-(3H-imidazol-4-yl)propanoate
CAS Registry NumberNot Available
SMILES
COC(=O)C(N)CC1=CN=CN1
InChI Identifier
InChI=1S/C7H11N3O2/c1-12-7(11)6(8)2-5-3-9-4-10-5/h3-4,6H,2,8H2,1H3,(H,9,10)
InChI KeyBXRMEWOQUXOLDH-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
  • Alpha-amino acid ester
  • Imidazolyl carboxylic acid derivative
  • Fatty acid ester
  • Aralkylamine
  • Fatty acyl
  • Azole
  • Imidazole
  • Methyl ester
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.2ChemAxon
pKa (Strongest Acidic)12.92ChemAxon
pKa (Strongest Basic)7.16ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area81 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity42.83 m³·mol⁻¹ChemAxon
Polarizability16.98 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID387055
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHistidine methyl ester
METLIN IDNot Available
PubChem Compound437593
PDB IDNot Available
ChEBI ID70961
Good Scents IDNot Available
References
General References
  1. Yilmaz GE, Saylan Y, Gokturk I, Yilmaz F, Denizli A: Selective Amplification of Plasmonic Sensor Signal for Cortisol Detection Using Gold Nanoparticles. Biosensors (Basel). 2022 Jul 1;12(7). pii: bios12070482. doi: 10.3390/bios12070482. [PubMed:35884285 ]
  2. Morsy MA, Patel SS, Bakrania A, Kandeel M, Nair AB, Shah JN, Akrawi SH, El-Daly M: Ameliorative Effect of a Neoteric Regimen of Catechin plus Cetirizine on Ovalbumin-Induced Allergic Rhinitis in Rats. Life (Basel). 2022 May 31;12(6). pii: life12060820. doi: 10.3390/life12060820. [PubMed:35743851 ]
  3. Yang JI, Lee HL, Yun JJ, Kim J, So KH, Jeong YI, Kang DH: pH and Redox-Dual Sensitive Chitosan Nanoparticles Having Methyl Ester and Disulfide Linkages for Drug Targeting against Cholangiocarcinoma Cells. Materials (Basel). 2022 May 26;15(11). pii: ma15113795. doi: 10.3390/ma15113795. [PubMed:35683095 ]
  4. Aylaz G, Andac M, Denizli A, Duman M: Recognition of human hemoglobin with macromolecularly imprinted polymeric nanoparticles using non-covalent interactions. J Mol Recognit. 2021 Dec;34(12):e2935. doi: 10.1002/jmr.2935. Epub 2021 Sep 2. [PubMed:34472144 ]
  5. Cimen D, Bereli N, Kartal F, Denizli A: Molecularly Imprinted Polymer-Based Quartz Crystal Microbalance Sensor for the Clinical Detection of Insulin. Methods Mol Biol. 2021;2359:209-222. doi: 10.1007/978-1-0716-1629-1_18. [PubMed:34410672 ]
  6. Cimen D, Asliyuce S, Tanalp TD, Denizli A: Molecularly imprinted nanofilms for endotoxin detection using an surface plasmon resonance sensor. Anal Biochem. 2021 Nov 1;632:114221. doi: 10.1016/j.ab.2021.114221. Epub 2021 May 5. [PubMed:33961908 ]
  7. Idil N, Bakhshpour M, Percin I, Mattiasson B: Whole Cell Recognition of Staphylococcus aureus Using Biomimetic SPR Sensors. Biosensors (Basel). 2021 Apr 29;11(5). pii: bios11050140. doi: 10.3390/bios11050140. [PubMed:33947112 ]
  8. Diken Gur S, Bakhshpour M, Bereli N, Denizli A: Antibacterial effect against both Gram-positive and Gram-negative bacteria via lysozyme imprinted cryogel membranes. J Biomater Sci Polym Ed. 2021 Jun;32(8):1024-1039. doi: 10.1080/09205063.2021.1892472. Epub 2021 Mar 11. [PubMed:33704023 ]
  9. Salha D, Andac M, Denizli A: Molecular docking of metal ion immobilized ligands to proteins in affinity chromatography. J Mol Recognit. 2021 Feb;34(2):e2875. doi: 10.1002/jmr.2875. Epub 2020 Sep 4. [PubMed:32886430 ]
  10. Smilowicz D, Metzler-Nolte N: Bioconjugates of Co(III) complexes with Schiff base ligands and cell penetrating peptides: Solid phase synthesis, characterization and antiproliferative activity. J Inorg Biochem. 2020 May;206:111041. doi: 10.1016/j.jinorgbio.2020.111041. Epub 2020 Feb 20. [PubMed:32120161 ]
  11. Ozgur E, Topcu AA, Yilmaz E, Denizli A: Surface plasmon resonance based biomimetic sensor for urinary tract infections. Talanta. 2020 May 15;212:120778. doi: 10.1016/j.talanta.2020.120778. Epub 2020 Jan 23. [PubMed:32113541 ]
  12. Razym G, Bakhshpour M, Yavuz H, Kip C, Tuncel A, Denizli A: Surface-imprinted silica particles for Concanavalin A purification from Canavalia ensiformis. J Chromatogr B Analyt Technol Biomed Life Sci. 2020 Jan 1;1136:121852. doi: 10.1016/j.jchromb.2019.121852. Epub 2019 Nov 21. [PubMed:31812006 ]
  13. Walsh AP, Laureanti JA, Katipamula S, Chambers GM, Priyadarshani N, Lense S, Bays JT, Linehan JC, Shaw WJ: Evaluating the impacts of amino acids in the second and outer coordination spheres of Rh-bis(diphosphine) complexes for CO2 hydrogenation. Faraday Discuss. 2019 Jul 4;215(0):123-140. doi: 10.1039/c8fd00164b. [PubMed:30993272 ]
  14. Kartal F, Cimen D, Bereli N, Denizli A: Molecularly imprinted polymer based quartz crystal microbalance sensor for the clinical detection of insulin. Mater Sci Eng C Mater Biol Appl. 2019 Apr;97:730-737. doi: 10.1016/j.msec.2018.12.086. Epub 2018 Dec 27. [PubMed:30678962 ]
  15. Feng W, Qiao J, Li D, Qi L: Chiral ligand exchange capillary electrochromatography with dual ligands for enantioseparation of D,L-amino acids. Talanta. 2019 Mar 1;194:430-436. doi: 10.1016/j.talanta.2018.10.059. Epub 2018 Oct 17. [PubMed:30609554 ]
  16. Bakhshpour M, Yavuz H, Denizli A: Controlled release of mitomycin C from PHEMAH-Cu(II) cryogel membranes. Artif Cells Nanomed Biotechnol. 2018;46(sup1):946-954. doi: 10.1080/21691401.2018.1439840. Epub 2018 Feb 19. [PubMed:29457925 ]
  17. Lozano-Torres B, Galiana I, Rovira M, Garrido E, Chaib S, Bernardos A, Munoz-Espin D, Serrano M, Martinez-Manez R, Sancenon F: An OFF-ON Two-Photon Fluorescent Probe for Tracking Cell Senescence in Vivo. J Am Chem Soc. 2017 Jul 5;139(26):8808-8811. doi: 10.1021/jacs.7b04985. Epub 2017 Jun 23. [PubMed:28625064 ]
  18. Percin I, Idil N, Bakhshpour M, Yilmaz E, Mattiasson B, Denizli A: Microcontact Imprinted Plasmonic Nanosensors: Powerful Tools in the Detection of Salmonella paratyphi. Sensors (Basel). 2017 Jun 13;17(6). pii: s17061375. doi: 10.3390/s17061375. [PubMed:28608810 ]
  19. Falcon-Gonzalez JM, Jimenez-Dominguez G, Ortega-Blake I, Carrillo-Tripp M: Multi-Phase Solvation Model for Biological Membranes: Molecular Action Mechanism of Amphotericin B. J Chem Theory Comput. 2017 Jul 11;13(7):3388-3397. doi: 10.1021/acs.jctc.7b00337. Epub 2017 Jun 7. [PubMed:28553993 ]
  20. Elkak A, Hamade A, Bereli N, Armutcu C, Denizli A: Synthesis of hydroxyethyl-methacrylate-(L)-histidine methyl ester cryogels. Application on the separation of bovine immunoglobulin G. Anal Biochem. 2017 May 15;525:1-7. doi: 10.1016/j.ab.2017.02.003. Epub 2017 Feb 21. [PubMed:28235457 ]
  21. LOTUS database [Link]