Record Information |
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Version | 1.0 |
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Created at | 2022-09-05 18:07:51 UTC |
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Updated at | 2022-09-05 18:07:51 UTC |
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NP-MRD ID | NP0217701 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | histidine methyl ester |
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Description | Histidine 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). |
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Structure | 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) |
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Synonyms | Value | Source |
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Methyl histidinate | ChEBI | Methyl histidinic acid | Generator |
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Chemical Formula | C7H11N3O2 |
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Average Mass | 169.1840 Da |
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Monoisotopic Mass | 169.08513 Da |
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IUPAC Name | methyl 2-amino-3-(1H-imidazol-5-yl)propanoate |
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Traditional Name | methyl 2-amino-3-(3H-imidazol-4-yl)propanoate |
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CAS Registry Number | Not Available |
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SMILES | COC(=O)C(N)CC1=CN=CN1 |
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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) |
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InChI Key | BXRMEWOQUXOLDH-UHFFFAOYSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | Not Available |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Histidine and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- LOTUS database [Link]
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