MiMeDB: Showing metabocard for N-(4-oxoglutaryl)-L-cysteinylglycine (MMDBc0054570)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:18:27 UTC

Update Date

2022-08-12 20:09:01 UTC

Metabolite ID

MMDBc0054570

Metabolite Identification

Common Name

N-(4-oxoglutaryl)-L-cysteinylglycine

Description

N-(4-oxoglutaryl)-L-cysteinylglycine, also known as deaminated glutathione, 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. N-(4-oxoglutaryl)-L-cysteinylglycine is a moderately basic compound (based on its pKa). A dipeptide that is glutathione in which the amino group on the glutamyl residue has been replaced by an oxo group.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05041406282D          

 21 20  0  0  1  0            999 V2000
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493   -1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349   -0.5230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493   -2.5855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059   -0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    1.9520    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  5  4  1  0  0  0  0
  6  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  3  1  4  0  0  0
 11  9  2  0  0  0  0
  5 12  1  1  0  0  0
 12  7  2  0  0  0  0
 13  6  2  0  0  0  0
  7 14  1  4  0  0  0
 15  8  2  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 10  2  0  0  0  0
 20  4  1  0  0  0  0
  5 21  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054570

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H14N2O7S/c13-6(10(18)19)1-2-7(14)12-5(4-20)9(17)11-3-8(15)16/h5,20H,1-4H2,(H,11,17)(H,12,14)(H,15,16)(H,18,19)/t5-/m0/s1

> <INCHI_KEY>
PMIVQUCENWNWHX-YFKPBYRVSA-N

> <FORMULA>
C10H14N2O7S

> <MOLECULAR_WEIGHT>
306.292

> <EXACT_MASS>
306.052171502

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
28.247777296921413

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-sulfanylethyl]-C-hydroxycarbonimidoyl}-2-oxobutanoic acid

> <ALOGPS_LOGP>
-1.30

> <JCHEM_LOGP>
-0.2129341287977798

> <ALOGPS_LOGS>
-3.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.8284896840472333

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.8672224531850685

> <JCHEM_PKA_STRONGEST_BASIC>
1.3710558680362024

> <JCHEM_POLAR_SURFACE_AREA>
156.85

> <JCHEM_REFRACTIVITY>
67.7536

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.55e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{[(1R)-1-(carboxymethyl-C-hydroxycarbonimidoyl)-2-sulfanylethyl]-C-hydroxycarbonimidoyl}-2-oxobutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   20  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
HETATM   21  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    7                                                       
CONECT    3    8   11                                                       
CONECT    4    5   20                                                       
CONECT    5    4    9   12   21                                             
CONECT    6    1   10   13                                                  
CONECT    7    2   12   14                                                  
CONECT    8    3   15   16                                                  
CONECT    9    5   11   17                                                  
CONECT   10    6   18   19                                                  
CONECT   11    3    9                                                       
CONECT   12    5    7                                                       
CONECT   13    6                                                            
CONECT   14    7                                                            
CONECT   15    8                                                            
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   10                                                            
CONECT   20    4                                                            
CONECT   21    5                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

Synonyms

Value	Source
Deaminated glutathione	ChEBI
gamma-(4-Oxoglutaryl)-L-cysteinylglycine	ChEBI
g-(4-Oxoglutaryl)-L-cysteinylglycine	Generator
Γ-(4-oxoglutaryl)-L-cysteinylglycine	Generator

Molecular Formula

C₁₀H₁₄N₂O₇S

Average Mass

306.292

Monoisotopic Mass

306.052171502

IUPAC Name

4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-sulfanylethyl]-C-hydroxycarbonimidoyl}-2-oxobutanoic acid

Traditional Name

4-{[(1R)-1-(carboxymethyl-C-hydroxycarbonimidoyl)-2-sulfanylethyl]-C-hydroxycarbonimidoyl}-2-oxobutanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H14N2O7S/c13-6(10(18)19)1-2-7(14)12-5(4-20)9(17)11-3-8(15)16/h5,20H,1-4H2,(H,11,17)(H,12,14)(H,15,16)(H,18,19)/t5-/m0/s1

InChI Key

PMIVQUCENWNWHX-YFKPBYRVSA-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
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Cysteine or derivatives
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Short-chain keto acid
Alpha-keto acid
Dicarboxylic acid or derivatives
Fatty amide
Keto acid
N-acyl-amine
Fatty acyl
Alpha-hydroxy ketone
Ketone
Carboxamide group
Secondary carboxylic acid amide
Alkylthiol
Carboxylic acid
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.16 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-0.21	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	2.87	ChemAxon
pKa (Strongest Basic)	1.37	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	156.85 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	67.75 m³·mol⁻¹	ChemAxon
Polarizability	28.25 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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 (TMS_1_5) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

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

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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
Bacteria	nah	2
Bacteria	Proteobacteria	3	Human
Eukaryota/Fungi	Ascomycota	1

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-19971

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71620685

PDB ID

KGT

ChEBI ID

138934

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for N-(4-oxoglutaryl)-L-cysteinylglycine (MMDBc0054570)

MOL for #<Metabolite:0x00007fdb44c53628>

3D MOL for #<Metabolite:0x00007fdb44c53628>

3D SDF for #<Metabolite:0x00007fdb44c53628>

3D-SDF for #<Metabolite:0x00007fdb44c53628>

PDB for #<Metabolite:0x00007fdb44c53628>

3D PDB for #<Metabolite:0x00007fdb44c53628>

SMILES for #<Metabolite:0x00007fdb44c53628>

INCHI for #<Metabolite:0x00007fdb44c53628>

Structure for #<Metabolite:0x00007fdb44c53628>

3D Structure for #<Metabolite:0x00007fdb44c53628>