Record Information |
---|
Version | 2.0 |
---|
Created at | 2022-05-12 15:18:03 UTC |
---|
Updated at | 2022-05-12 15:18:03 UTC |
---|
NP-MRD ID | NP0136574 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | Methionyl-Glycine |
---|
Description | Methionyl-Glycine, also known as m-g dipeptide or met-gly, 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. Methionyl-Glycine is a very strong basic compound (based on its pKa). Methionyl-Glycine is a dipeptide composed of methionine and glycine. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite. 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. Methionyl-Glycine was first documented in 1980 (PMID: 6778594). It is an incomplete breakdown product of protein digestion or protein catabolism (PMID: 19438284) (PMID: 17223197) (PMID: 9814913) (PMID: 7118410) (PMID: 8818821) (PMID: 8215272). |
---|
Structure | InChI=1S/C7H14N2O3S/c1-13-3-2-5(8)7(12)9-4-6(10)11/h5H,2-4,8H2,1H3,(H,9,12)(H,10,11) |
---|
Synonyms | Value | Source |
---|
L-Methionyl-L-glycine | HMDB | m-g Dipeptide | HMDB | Met-gly | HMDB | Methionine glycine dipeptide | HMDB | Methionine-glycine dipeptide | HMDB | Methionylglycine | HMDB | MG Dipeptide | HMDB | 2-{[2-amino-1-hydroxy-4-(methylsulfanyl)butylidene]amino}acetate | Generator | 2-{[2-amino-1-hydroxy-4-(methylsulphanyl)butylidene]amino}acetate | Generator | 2-{[2-amino-1-hydroxy-4-(methylsulphanyl)butylidene]amino}acetic acid | Generator |
|
---|
Chemical Formula | C7H14N2O3S |
---|
Average Mass | 206.2630 Da |
---|
Monoisotopic Mass | 206.07251 Da |
---|
IUPAC Name | 2-[2-amino-4-(methylsulfanyl)butanamido]acetic acid |
---|
Traditional Name | [2-amino-4-(methylsulfanyl)butanamido]acetic acid |
---|
CAS Registry Number | Not Available |
---|
SMILES | CSCCC(N)C(=O)NCC(O)=O |
---|
InChI Identifier | InChI=1S/C7H14N2O3S/c1-13-3-2-5(8)7(12)9-4-6(10)11/h5H,2-4,8H2,1H3,(H,9,12)(H,10,11) |
---|
InChI Key | QXOHLNCNYLGICT-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
- Methionine or derivatives
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- Alpha-amino acid amide
- Alpha-amino acid or derivatives
- Fatty amide
- Fatty acyl
- N-acyl-amine
- Amino acid or derivatives
- Carboxamide group
- Amino acid
- Secondary carboxylic acid amide
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Dialkylthioether
- Sulfenyl compound
- Thioether
- Amine
- Organic oxygen compound
- Organic nitrogen compound
- Primary aliphatic amine
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Organopnictogen compound
- Organonitrogen compound
- Organooxygen compound
- Organosulfur compound
- Primary amine
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic 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 | - Morozova OB, Korchak SE, Vieth HM, Yurkovskaya AV: Photo-CIDNP study of transient radicals of Met-Gly and Gly-Met peptides in aqueous solution at variable pH. J Phys Chem B. 2009 May 21;113(20):7398-406. doi: 10.1021/jp8112182. [PubMed:19438284 ]
- Paquet A, Sarwar G: Determination of bioavailability of some long-chain N-substituted derivatives of L-methionine and L-lysine. Can J Biochem. 1980 Jul;58(7):577-80. doi: 10.1139/o80-079. [PubMed:6778594 ]
- Kaluderovic GN, Schmidt H, Paschke R, Kalinowski B, Dietrich A, Mueller T, Steinborn D: Platinum(II) complexes with l-methionylglycine and l-methionyl-l-leucine ligands: synthesis, characterization and in vitro antitumoral activity. J Inorg Biochem. 2007 Mar;101(3):543-9. doi: 10.1016/j.jinorgbio.2006.11.016. Epub 2006 Nov 30. [PubMed:17223197 ]
- McCollum MQ, Webb KE Jr: Glycyl-L-sarcosine absorption across ovine omasal epithelium during coincubation with other peptide substrates and volatile fatty acids. J Anim Sci. 1998 Oct;76(10):2706-11. doi: 10.2527/1998.76102706x. [PubMed:9814913 ]
- Bressan M, Ettorre R, Marchiori F, Valle G: Coordination chemistry of peptides. Part II. Crystal structure of cyclo-L-methionylglycine and studies of metal complexation. Int J Pept Protein Res. 1982 Apr;19(4):402-7. [PubMed:7118410 ]
- Matthews JC, Wong EA, Bender PK, Bloomquist JR, Webb KE Jr: Demonstration and characterization of dipeptide transport system activity in sheep omasal epithelium by expression of mRNA in Xenopus laevis oocytes. J Anim Sci. 1996 Jul;74(7):1720-7. doi: 10.2527/1996.7471720x. [PubMed:8818821 ]
- Callaway JE, Lai J, Haselbeck B, Baltaian M, Bonnesen SP, Weickmann J, Wilcox G, Lei SP: Modification of the C terminus of cecropin is essential for broad-spectrum antimicrobial activity. Antimicrob Agents Chemother. 1993 Aug;37(8):1614-9. doi: 10.1128/AAC.37.8.1614. [PubMed:8215272 ]
- Moneton P, Sarthou P, Le Goffic F: Transport and hydrolysis of peptides in Saccharomyces cerevisiae. J Gen Microbiol. 1986 Aug;132(8):2147-53. doi: 10.1099/00221287-132-8-2147. [PubMed:3540196 ]
- Matthews JC, Webb KE Jr: Absorption of L-carnosine, L-methionine, and L-methionylglycine by isolated sheep ruminal and omasal epithelial tissue. J Anim Sci. 1995 Nov;73(11):3464-75. doi: 10.2527/1995.73113464x. [PubMed:8586607 ]
|
---|