MiMeDB: Showing metabocard for gamma-Glutamylglycine (MMDBc0000453)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:38:06 UTC

Update Date

2024-04-30 19:32:27 UTC

Metabolite ID

MMDBc0000453

Metabolite Identification

Common Name

gamma-Glutamylglycine

Description

gamma-Glutamylglycine is one of the dipeptides that is commonly produced from polypeptides by the action of the enzyme dipeptidyl peptidase. Dietary proteins are digested to dipeptides and amino acids, and the dipeptides are absorbed more rapidly than the amino acids because their uptake involves a separate mechanism. Dipeptides activate G-cells found in the stomach to secrete gastrin. gamma-Glutamylglycine is an excitatory amino acid receptor antagonist with a structure similar to gamma-aminobutyric acid (GABA) (PMID: 6146532 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

      
  Mrv1652312081700042D          

 14 13  0  0  0  0            999 V2000
 2500.3574 2500.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6425 2499.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9276 2500.2058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2123 2499.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.4975 2500.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.7826 2499.7940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.4975 2501.0315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6425 2498.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0723 2499.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7875 2500.2058    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2502.5023 2499.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.2172 2500.2058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.5023 2498.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7875 2501.0315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  0  0  0  0
  2  3  1  0  0  0  0
  2  8  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 14  1  6  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000453

> <DATABASE_NAME>
MIME

> <SMILES>
N[C@@H](CCC(=O)NCC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H12N2O5/c8-4(7(13)14)1-2-5(10)9-3-6(11)12/h4H,1-3,8H2,(H,9,10)(H,11,12)(H,13,14)/t4-/m0/s1

> <INCHI_KEY>
ACIJGUBIMXQCMF-BYPYZUCNSA-N

> <FORMULA>
C7H12N2O5

> <MOLECULAR_WEIGHT>
204.1806

> <EXACT_MASS>
204.074621504

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
18.815391233414246

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-[(carboxymethyl)carbamoyl]butanoic acid

> <ALOGPS_LOGP>
-3.47

> <JCHEM_LOGP>
-4.386040058717441

> <ALOGPS_LOGS>
-0.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.777323269397436

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8299819439990146

> <JCHEM_PKA_STRONGEST_BASIC>
9.312086338522867

> <JCHEM_POLAR_SURFACE_AREA>
129.72

> <JCHEM_REFRACTIVITY>
44.0912

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.12e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-4-(carboxymethylcarbamoyl)butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-DEC-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-DEC-17         0                                  
HETATM    1  C   UNK     0    4667.3344667.051   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4665.9994666.282   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    4664.6654667.051   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    4663.3304666.282   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4661.9954667.051   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    4660.6614666.282   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    4661.9954668.592   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    4665.9994664.741   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    4668.6684666.282   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    4670.0034667.051   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    4671.3384666.282   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    4672.6724667.051   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    4671.3384664.741   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0    4670.0034668.592   0.000  0.00  0.00           N+0
CONECT    1    2    9                                                       
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    2                                                            
CONECT    9    1   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

Synonyms

Value	Source
5-L-Glutamylglycine	ChEBI
gamma-L-Glu-gly	ChEBI
L-gamma-Glu-gly	ChEBI
N-L-gamma-Glutamylglycine	ChEBI
g-L-Glu-gly	Generator
Γ-L-glu-gly	Generator
L-g-Glu-gly	Generator
L-Γ-glu-gly	Generator
N-L-g-Glutamylglycine	Generator
N-L-Γ-glutamylglycine	Generator
g-Glutamylglycine	Generator
Γ-glutamylglycine	Generator
γ-Glu-Gly	HMDB, Generator
γ-L-Glutamylglycine	HMDB
L-γ-Glutamylglycine	HMDB
N-γ-Glutamylglycine	HMDB
N-γ-L-Glutamylglycine	HMDB
gamma-Glu-Gly	HMDB
gamma-L-Glutamylglycine	HMDB
L-gamma-Glutamylglycine	HMDB
N-gamma-Glutamylglycine	HMDB
N-gamma-L-Glutamylglycine	HMDB
N-(Carboxymethyl)-glutamine	HMDB
L-N-(Carboxymethyl)-glutamine	HMDB
gamma-Glutamylglycine	HMDB, MeSH
5-L-Glutamyl-glycine	HMDB
gamma-Glutamyl glycine	HMDB
gamma-L-Glutamyl-glycine	HMDB
N-L-gamma-Glutamyl-glycine	HMDB
g-Glu-Gly	Generator, HMDB

Molecular Formula

C₇H₁₂N₂O₅

Average Mass

204.1806

Monoisotopic Mass

204.074621504

IUPAC Name

(2S)-2-amino-4-[(carboxymethyl)carbamoyl]butanoic acid

Traditional Name

(2S)-2-amino-4-(carboxymethylcarbamoyl)butanoic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](CCC(=O)NCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C7H12N2O5/c8-4(7(13)14)1-2-5(10)9-3-6(11)12/h4H,1-3,8H2,(H,9,10)(H,11,12)(H,13,14)/t4-/m0/s1

InChI Key

ACIJGUBIMXQCMF-BYPYZUCNSA-N

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
Gamma-glutamyl alpha-amino acid
Glutamine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
N-acyl-amine
Fatty amide
Dicarboxylic acid or derivatives
Fatty acid
Fatty acyl
Carboxamide group
Secondary carboxylic acid amide
Amino acid
Amino acid or derivatives
Carboxylic acid
Organic nitrogen compound
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:73845 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	21.2 g/L	ALOGPS
logP	-3.5	ALOGPS
logP	-4.4	ChemAxon
logS	-0.98	ALOGPS
pKa (Strongest Acidic)	1.83	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	129.72 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	44.09 m³·mol⁻¹	ChemAxon
Polarizability	18.82 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0536-9600000000-f3713ba3276d2d960d27	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0089-7491000000-4cf0c60c40ac1ebb4a76	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-1920000000-4f37f0492e666f37c892	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-7900000000-7afc277125515fcc2232	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9100000000-298d0d22ca619d4701c0	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0790000000-d8cc1593c46460175daa	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zg0-1930000000-7a4e5669b96e70411b48	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9200000000-71292eef73981043b665	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-2900000000-850fda337bef74e3fc91	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fki-7910000000-04a3e783689357c0f7d5	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-38fe5d70392f90ae21bb	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a5i-2970000000-90491b3f0955e2d88a75	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9400000000-efb1bd9a2f2c091cad62	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ac0-9000000000-6025fc2c42c63c057129	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	5	Human stool; Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Proteobacteria	1	Human stool; Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0011667

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028356

KNApSAcK ID

Not Available

Chemspider ID

145071

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

165527

PDB ID

Not Available

ChEBI ID

73845

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Sawada S, Yamamoto C: Gamma-D-glutamylglycine and cis-2,3-piperidine dicarboxylate as antagonists of excitatory amino acids in the hippocampus. Exp Brain Res. 1984;55(2):351-8. doi: 10.1007/BF00237285. [PubMed:6146532 ]

Showing metabocard for gamma-Glutamylglycine (MMDBc0000453)

MOL for #<Metabolite:0x00007fecc0225420>

3D MOL for #<Metabolite:0x00007fecc0225420>

3D SDF for #<Metabolite:0x00007fecc0225420>

3D-SDF for #<Metabolite:0x00007fecc0225420>

PDB for #<Metabolite:0x00007fecc0225420>

3D PDB for #<Metabolite:0x00007fecc0225420>

SMILES for #<Metabolite:0x00007fecc0225420>

INCHI for #<Metabolite:0x00007fecc0225420>

Structure for #<Metabolite:0x00007fecc0225420>

3D Structure for #<Metabolite:0x00007fecc0225420>