Record Information |
---|
Version | 1.0 |
---|
Created at | 2022-05-12 15:15:08 UTC |
---|
Updated at | 2022-05-12 15:15:08 UTC |
---|
NP-MRD ID | NP0136461 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | Glycyl-Histidine |
---|
Description | Glycyl-Histidine, also known as g-H dipeptide or gly-his, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Glycyl-Histidine is a very strong basic compound (based on its pKa). Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. Glycyl-Histidine is a dipeptide composed of glycine and histidine. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite. It was first documented in 1989 (PMID: 2539111). It is an incomplete breakdown product of protein digestion or protein catabolism (PMID: 17157529) (PMID: 15137808) (PMID: 17574763) (PMID: 19388698) (PMID: 16358024) (PMID: 18459719). |
---|
Structure | NCC(=O)NC(CC1=CN=CN1)C(O)=O InChI=1S/C8H12N4O3/c9-2-7(13)12-6(8(14)15)1-5-3-10-4-11-5/h3-4,6H,1-2,9H2,(H,10,11)(H,12,13)(H,14,15) |
---|
Synonyms | Value | Source |
---|
g-H Dipeptide | HMDB | GH Dipeptide | HMDB | Gly-his | HMDB | Glycine histidine dipeptide | HMDB | Glycine-histidine dipeptide | HMDB | Glycylhistidine | HMDB | L-Glycyl-L-histidine | HMDB | Glycyl-L-histidine | HMDB | Glycylhistidine, monohydrochloride | HMDB | 2-[(2-Amino-1-hydroxyethylidene)amino]-3-(1H-imidazol-5-yl)propanoate | Generator |
|
---|
Chemical Formula | C8H12N4O3 |
---|
Average Mass | 212.2059 Da |
---|
Monoisotopic Mass | 212.09094 Da |
---|
IUPAC Name | 2-(2-aminoacetamido)-3-(1H-imidazol-5-yl)propanoic acid |
---|
Traditional Name | 2-(2-aminoacetamido)-3-(3H-imidazol-4-yl)propanoic acid |
---|
CAS Registry Number | Not Available |
---|
SMILES | NCC(=O)NC(CC1=CN=CN1)C(O)=O |
---|
InChI Identifier | InChI=1S/C8H12N4O3/c9-2-7(13)12-6(8(14)15)1-5-3-10-4-11-5/h3-4,6H,1-2,9H2,(H,10,11)(H,12,13)(H,14,15) |
---|
InChI Key | YIWFXZNIBQBFHR-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, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, 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 dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic acids and derivatives |
---|
Class | Carboxylic acids and derivatives |
---|
Sub Class | Amino acids, peptides, and analogues |
---|
Direct Parent | Dipeptides |
---|
Alternative Parents | |
---|
Substituents | - Alpha-dipeptide
- Histidine or derivatives
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- Alpha-amino acid amide
- Alpha-amino acid or derivatives
- Imidazolyl carboxylic acid derivative
- Azole
- Imidazole
- Heteroaromatic compound
- Secondary carboxylic acid amide
- Amino acid or derivatives
- Amino acid
- Carboxamide group
- Organoheterocyclic compound
- Carboxylic acid
- Azacycle
- Monocarboxylic acid or derivatives
- Organic nitrogen compound
- Primary aliphatic amine
- Organonitrogen compound
- Organooxygen compound
- Primary amine
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- Organopnictogen compound
- Amine
- Organic oxygen compound
- Aromatic heteromonocyclic compound
|
---|
Molecular Framework | Aromatic heteromonocyclic compounds |
---|
External Descriptors | Not Available |
---|
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 | |
---|
General References | - Wang P, Wesdemiotis C, Kapota C, Ohanessian G: The sodium ion affinities of simple di-, tri-, and tetrapeptides. J Am Soc Mass Spectrom. 2007 Mar;18(3):541-52. Epub 2006 Dec 8. [PubMed:17157529 ]
- Girelli AM, Mattei E, Messina A, Tarola AM: Inhibition of polyphenol oxidases activity by various dipeptides. J Agric Food Chem. 2004 May 19;52(10):2741-5. doi: 10.1021/jf0305276. [PubMed:15137808 ]
- Islam MK, Tsuboya C, Kusaka H, Aizawa S, Ueki T, Michibata H, Kanamori K: Reduction of vanadium(V) to vanadium(IV) by NADPH, and vanadium(IV) to vanadium(III) by cysteine methyl ester in the presence of biologically relevant ligands. Biochim Biophys Acta. 2007 Aug;1770(8):1212-8. doi: 10.1016/j.bbagen.2007.05.003. Epub 2007 May 21. [PubMed:17574763 ]
- Turecek F, Yao C, Fung YM, Hayakawa S, Hashimoto M, Matsubara H: Histidine-containing radicals in the gas phase. J Phys Chem B. 2009 May 21;113(20):7347-66. doi: 10.1021/jp900719n. [PubMed:19388698 ]
- Inoue S, Kawanishi S: ESR evidence for superoxide, hydroxyl radicals and singlet oxygen produced from hydrogen peroxide and nickel(II) complex of glycylglycyl-L-histidine. Biochem Biophys Res Commun. 1989 Mar 15;159(2):445-51. doi: 10.1016/0006-291x(89)90012-0. [PubMed:2539111 ]
- Kapota C, Ohanessian G: The low energy tautomers and conformers of the dipeptides HisGly and GlyHis and of their sodium ion complexes in the gas phase. Phys Chem Chem Phys. 2005 Nov 7;7(21):3744-55. doi: 10.1039/b508092d. Epub 2005 Sep 9. [PubMed:16358024 ]
- Casella G, Ferrante F, Saielli G: DFT calculation of 1J(119Sn,13C) and 2J(119Sn,1H) coupling constants in di- and trimethyltin(IV) compounds. Inorg Chem. 2008 Jun 2;47(11):4796-807. doi: 10.1021/ic8000976. Epub 2008 May 6. [PubMed:18459719 ]
- Zhang J, Yu X, Zeng B, Cai S, Chen Z: Spectroscopic and theoretical study on the interaction between diperoxovanadate complexes and glycyl-histidine. Spectrochim Acta A Mol Biomol Spectrosc. 2010 Nov;77(4):825-31. doi: 10.1016/j.saa.2010.08.013. Epub 2010 Aug 11. [PubMed:20822949 ]
|
---|