NP-MRD: Showing NP-Card for N-gamma-Glutamylglutamine (NP0136722)

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Record Information

Version

2.0

Created at

2022-05-12 15:21:49 UTC

Updated at

2022-05-12 15:21:49 UTC

NP-MRD ID

NP0136722

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-gamma-Glutamylglutamine

Description

N-gamma-Glutamylglutamine, also known as L-γ-glutamyl-L-glutamine or bis-g-glutamylamine, belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-gamma-Glutamylglutamine is a very strong basic compound (based on its pKa). N-gamma-Glutamylglutamine, with regard to humans, has been found to be associated with several diseases such as schizophrenia, hyperammonemia, iron deficiency, and crohn's disease; N-gamma-glutamylglutamine has also been linked to the inborn metabolic disorder gamma-glutamyltransferase deficiency.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 35  0  0  0  0  0  0  0  0999 V2000
    5.7852    0.5583   -0.3535 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4628   -0.1183   -0.2713 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9949    0.0742    1.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6699   -0.4591    1.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5005    0.1765    0.8787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5990    1.2714    0.2887 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2447   -0.4594    0.9444 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8734    0.1722    0.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7711    1.2721   -0.2594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2393   -0.4690    0.3757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2006    0.4260   -0.3467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5833   -0.1611   -0.3793 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4881    0.7593   -1.1061 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0910   -0.3805    0.9845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0227    0.3250    1.4264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5453   -1.3636    1.7766 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6010    0.3149   -1.3572 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7134    1.4086   -1.9662 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5578   -0.5369   -1.7852 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9246    0.8155   -1.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6724    1.4333    0.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7391   -1.2020   -0.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1431    1.1477    1.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7611   -0.4639    1.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5604   -0.4595    2.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6998   -1.5705    1.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1260   -1.3873    1.4362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5067   -0.5055    1.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1971   -1.4826   -0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9008    0.5641   -1.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1973    1.4437    0.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5981   -1.1080   -0.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1807    1.7367   -0.8634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3065    0.5748   -2.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7194   -1.4790    2.7625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6656   -0.8686   -2.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 16  1  0
 14 15  2  0
  2 17  1  0
 17 19  1  0
 17 18  2  0
  1 20  1  0
  1 21  1  0
  2 22  1  6
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  7 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  6
 13 33  1  0
 13 34  1  0
 16 35  1  0
 19 36  1  0
M  END

      
  Mrv1652304062014282D          

 19 18  0  0  0  0            999 V2000
 2499.9989 2499.7940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7138 2500.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4308 2499.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1460 2500.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.8609 2499.7940    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2503.5758 2500.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2504.2907 2499.7940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2503.5758 2501.0315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.8609 2498.9684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7138 2501.0315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2840 2500.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.5691 2499.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8538 2500.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.1390 2499.7940    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2496.4241 2500.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2495.7091 2499.7940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2496.4241 2501.0315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.1390 2498.9684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2840 2501.0315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  2 10  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  9  1  1  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
 11 12  1  0  0  0  0
 11 19  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 18  1  6  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136722

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H17N3O6/c11-5(9(16)17)1-3-7(14)13-8(15)4-2-6(12)10(18)19/h5-6H,1-4,11-12H2,(H,16,17)(H,18,19)(H,13,14,15)/t5-,6-/m0/s1

> <INCHI_KEY>
FCWNOQOVMGNKNG-WDSKDSINSA-N

> <FORMULA>
C10H17N3O6

> <MOLECULAR_WEIGHT>
275.261

> <EXACT_MASS>
275.111735279

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
26.1669980274238

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-5-[(4S)-4-amino-4-carboxybutanamido]-5-oxopentanoic acid

> <ALOGPS_LOGP>
-3.90

> <JCHEM_LOGP>
-6.983757363750202

> <ALOGPS_LOGS>
-1.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
2.242094757818342

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.640034797806286

> <JCHEM_PKA_STRONGEST_BASIC>
9.710479523751545

> <JCHEM_POLAR_SURFACE_AREA>
172.81

> <JCHEM_REFRACTIVITY>
61.31980000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.53e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-5-[(4S)-4-amino-4-carboxybutanamido]-5-oxopentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  N   UNK     0    4666.6654666.282   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0    4667.9994667.051   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    4669.3374666.282   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4670.6734667.051   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4672.0074666.282   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4673.3414667.051   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    4674.6764666.282   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    4673.3414668.592   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0    4672.0074664.741   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0    4667.9994668.592   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    4665.3304667.051   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    4663.9964666.282   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4662.6604667.051   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4661.3264666.282   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4659.9924667.051   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    4658.6574666.282   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    4659.9924668.592   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0    4661.3264664.741   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0    4665.3304668.592   0.000  0.00  0.00           O+0
CONECT    1    2   11                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5                                                            
CONECT   10    2                                                            
CONECT   11    1   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   14                                                            
CONECT   19   11                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

View in JSmol

Synonyms

Value	Source
N-g-Glutamylglutamine	Generator
N-Γ-glutamylglutamine	Generator
Bis-g-glutamylamine	HMDB
Bis-γ-glutamylamine	HMDB
Γ-glu-GLN	HMDB
Γ-L-glu-L-GLN	HMDB
Γ-glutamylglutamine	HMDB
Γ-L-glutamyl-L-glutamine	HMDB
L-Γ-glutamyl-L-glutamine	HMDB
N-L-Γ-glutamylglutamine	HMDB
N-L-Γ-glutamyl-L-glutamine	HMDB
gamma-Glu-GLN	HMDB
gamma-L-Glu-L-GLN	HMDB
gamma-Glutamylglutamine	HMDB
gamma-L-Glutamyl-L-glutamine	HMDB
L-gamma-Glutamyl-L-glutamine	HMDB
N-L-gamma-Glutamylglutamine	HMDB
N-L-gamma-Glutamyl-L-glutamine	HMDB
N-gamma-Glutamylglutamine	HMDB
(2S)-2-Amino-4-{[(4S)-4-amino-4-carboxybutanoyl]-C-hydroxycarbonimidoyl}butanoate	Generator

Chemical Formula

C₁₀H₁₇N₃O₆

Average Mass

275.2610 Da

Monoisotopic Mass

275.11174 Da

IUPAC Name

(2S)-2-amino-5-[(4S)-4-amino-4-carboxybutanamido]-5-oxopentanoic acid

Traditional Name

(2S)-2-amino-5-[(4S)-4-amino-4-carboxybutanamido]-5-oxopentanoic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](CCC(=O)NC(=O)CC[C@H](N)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C10H17N3O6/c11-5(9(16)17)1-3-7(14)13-8(15)4-2-6(12)10(18)19/h5-6H,1-4,11-12H2,(H,16,17)(H,18,19)(H,13,14,15)/t5-,6-/m0/s1

InChI Key

FCWNOQOVMGNKNG-WDSKDSINSA-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 glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamine and derivatives

Alternative Parents

Substituents

Glutamine or derivatives
Alpha-amino acid
L-alpha-amino acid
Dicarboxylic acid or derivatives
Fatty acid
N-acyl-amine
Carboxylic acid imide
Dicarboximide
Carboxylic acid imide, n-unsubstituted
Amino acid
Carboxylic acid
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
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	-3.9	ALOGPS
logP	-7	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	1.64	ChemAxon
pKa (Strongest Basic)	9.71	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.81 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	61.32 m³·mol⁻¹	ChemAxon
Polarizability	26.17 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

HMDB0029147

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

21122973

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for N-gamma-Glutamylglutamine (NP0136722)

MOL for NP0136722 (N-gamma-Glutamylglutamine)

3D MOL for NP0136722 (N-gamma-Glutamylglutamine)

3D SDF for NP0136722 (N-gamma-Glutamylglutamine)

3D-SDF for NP0136722 (N-gamma-Glutamylglutamine)

PDB for NP0136722 (N-gamma-Glutamylglutamine)

3D PDB for NP0136722 (N-gamma-Glutamylglutamine)

SMILES for NP0136722 (N-gamma-Glutamylglutamine)

INCHI for NP0136722 (N-gamma-Glutamylglutamine)

Structure for NP0136722 (N-gamma-Glutamylglutamine)

3D Structure for NP0136722 (N-gamma-Glutamylglutamine)