NP-MRD: Showing NP-Card for histidine methyl ester (NP0217701)

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Record Information

Version

2.0

Created at

2022-09-05 18:07:51 UTC

Updated at

2022-09-05 18:07:51 UTC

NP-MRD ID

NP0217701

Secondary Accession Numbers

None

Natural Product Identification

Common Name

histidine methyl ester

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. histidine methyl ester 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

MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       1.255  -3.725   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.589  -4.495   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.923  -3.725   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.923  -2.185   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.256  -4.495   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       5.256  -6.035   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       6.590  -3.725   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.924  -4.495   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.331  -3.869   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      10.361  -5.013   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       9.591  -6.347   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       8.085  -6.027   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol

Synonyms

Value	Source
Methyl histidinate	ChEBI
Methyl histidinic acid	Generator

Chemical Formula

C₇H₁₁N₃O₂

Average Mass

169.1840 Da

Monoisotopic Mass

169.08513 Da

IUPAC Name

methyl 2-amino-3-(1H-imidazol-5-yl)propanoate

Traditional Name

methyl 2-amino-3-(3H-imidazol-4-yl)propanoate

CAS Registry Number

Not 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 Key

BXRMEWOQUXOLDH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
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

Not Available

Species

Species of Origin

Not 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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Histidine 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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

methyl ester (CHEBI:70961 )
alpha-amino acid ester (CHEBI:70961 )
histidine derivative (CHEBI:70961 )
an amino acid derivative (CPD-10907 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.2	ChemAxon
pKa (Strongest Acidic)	12.92	ChemAxon
pKa (Strongest Basic)	7.16	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	81 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	42.83 m³·mol⁻¹	ChemAxon
Polarizability	16.98 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

387055

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Histidine methyl ester

METLIN ID

Not Available

PubChem Compound

437593

PDB ID

Not Available

ChEBI ID

70961

Good Scents ID

Not Available

References

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]

Showing NP-Card for histidine methyl ester (NP0217701)

MOL for NP0217701 (histidine methyl ester)

3D MOL for NP0217701 (histidine methyl ester)

3D SDF for NP0217701 (histidine methyl ester)

3D-SDF for NP0217701 (histidine methyl ester)

PDB for NP0217701 (histidine methyl ester)

3D PDB for NP0217701 (histidine methyl ester)

SMILES for NP0217701 (histidine methyl ester)

INCHI for NP0217701 (histidine methyl ester)

Structure for NP0217701 (histidine methyl ester)

3D Structure for NP0217701 (histidine methyl ester)