NP-MRD: Showing NP-Card for Methionyl-Glycine (NP0136574)

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Record Information

Version

1.0

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. It 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

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304062014022D          

 13 12  0  0  0  0            999 V2000
    6.5704    2.1434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    1.3184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136574

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C7H14N2O3S

> <MOLECULAR_WEIGHT>
206.263

> <EXACT_MASS>
206.072513014

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
21.23162973144014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[2-amino-4-(methylsulfanyl)butanamido]acetic acid

> <ALOGPS_LOGP>
-1.87

> <JCHEM_LOGP>
-3.297053365324612

> <ALOGPS_LOGS>
-1.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.41414676114136

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.779640236836783

> <JCHEM_PKA_STRONGEST_BASIC>
8.416208381849241

> <JCHEM_POLAR_SURFACE_AREA>
92.42000000000002

> <JCHEM_REFRACTIVITY>
50.389500000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[2-amino-4-(methylsulfanyl)butanamido]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  N   UNK     0      12.265   4.001   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      10.931   6.311   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       9.597   2.461   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    8  S   UNK     0       5.596   4.771   0.000  0.00  0.00           S+0
HETATM    9  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    1   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol

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

Property	Value	Source
logP	-1.9	ALOGPS
logP	-3.3	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	3.78	ChemAxon
pKa (Strongest Basic)	8.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.42 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	50.39 m³·mol⁻¹	ChemAxon
Polarizability	21.23 Å³	ChemAxon
Number of Rings	0	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

HMDB0028973

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

259185

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

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 ]

Showing NP-Card for Methionyl-Glycine (NP0136574)

MOL for NP0136574 (Methionyl-Glycine)

3D MOL for NP0136574 (Methionyl-Glycine)

3D SDF for NP0136574 (Methionyl-Glycine)

3D-SDF for NP0136574 (Methionyl-Glycine)

PDB for NP0136574 (Methionyl-Glycine)

3D PDB for NP0136574 (Methionyl-Glycine)

SMILES for NP0136574 (Methionyl-Glycine)

INCHI for NP0136574 (Methionyl-Glycine)

Structure for NP0136574 (Methionyl-Glycine)

3D Structure for NP0136574 (Methionyl-Glycine)