NP-MRD: Showing NP-Card for 5-L-Glutamyl-L-alanine (NP0085720)

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Record Information

Version

2.0

Created at

2022-04-29 06:12:05 UTC

Updated at

2022-04-29 06:12:05 UTC

NP-MRD ID

NP0085720

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-L-Glutamyl-L-alanine

Description

Gamma-Glutamylalanine, also known as 5-L-glutamyl-L-alanine or L-gamma-glu-L-ala, 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. Gamma-Glutamylalanine is a very strong basic compound (based on its pKa). Gamma-Glutamylalanine exists in all eukaryotes, ranging from yeast to humans. 5-L-Glutamyl-L-alanine is found in Annona squamosa and Dietes iridioides. 5-L-Glutamyl-L-alanine was first documented in 1964 (PMID: 14213360). A gamma-glutamylalanine obtained by formal condensation of the gamma-carboxy group of L-glutamic acid with the amino group of L-alanine (PMID: 2570694).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 28  0  0  0  0  0  0  0  0999 V2000
   -3.8245    1.0783    0.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9032   -0.0884    0.6974 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6917   -0.0330   -0.0954 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4046    0.0608    0.4960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3233    0.0963    1.7463 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8409    0.1183   -0.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0172    0.2127    0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3338    0.2767   -0.1008 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4753    1.3933   -0.9785 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6194   -1.0203   -0.7566 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5444   -2.1088   -0.1371 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9813   -1.0575   -2.0909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5812   -1.3911    0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0956   -2.2252   -0.3724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7753   -1.7125    1.0582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3712    1.6885   -0.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9520    1.7548    1.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8506    0.7301    0.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7026   -0.0497    1.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7339   -0.0610   -1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7505    0.9648   -1.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9677   -0.8010   -0.9247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9263    1.1333    1.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0278   -0.7058    1.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1211    0.3898    0.7019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8739    2.2000   -0.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4673    1.7636   -0.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9482   -1.1748   -2.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6856   -1.4323    0.7153 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 12  1  0
 10 11  2  0
  2 13  1  0
 13 15  1  0
 13 14  2  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  1
  3 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  1
  9 26  1  0
  9 27  1  0
 12 28  1  0
 15 29  1  0
M  END

      
  Mrv1652312091700132D          

 15 14  0  0  0  0            999 V2000
 2498.9276 2500.2058    0.0000 N   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
 2500.3574 2500.2058    0.0000 C   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
 2499.6425 2498.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2123 2499.7940    0.0000 C   0  0  2  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
 2498.2123 2498.9684    0.0000 C   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  6  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 15  1  1  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0085720

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H14N2O5/c1-4(7(12)13)10-6(11)3-2-5(9)8(14)15/h4-5H,2-3,9H2,1H3,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1

> <INCHI_KEY>
WQXXXVRAFAKQJM-WHFBIAKZSA-N

> <FORMULA>
C8H14N2O5

> <MOLECULAR_WEIGHT>
218.2072

> <EXACT_MASS>
218.090271568

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
20.935963393730972

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-{[(1S)-1-carboxyethyl]carbamoyl}butanoic acid

> <ALOGPS_LOGP>
-3.36

> <JCHEM_LOGP>
-3.8159177947397183

> <ALOGPS_LOGS>
-1.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.825455393275773

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9295800715632931

> <JCHEM_PKA_STRONGEST_BASIC>
9.312086881878784

> <JCHEM_POLAR_SURFACE_AREA>
129.71999999999997

> <JCHEM_REFRACTIVITY>
48.58510000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
g-glu-ala

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-DEC-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-DEC-17         0                                  
HETATM    1  N   UNK     0    4664.6654667.051   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0    4665.9994666.282   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    4667.3344667.051   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4668.6684666.282   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4670.0034667.051   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4671.3384666.282   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    4672.6724667.051   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    4671.3384664.741   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0    4670.0034668.592   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0    4665.9994664.741   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    4663.3304666.282   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    4661.9954667.051   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    4660.6614666.282   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    4661.9954668.592   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    4663.3304664.741   0.000  0.00  0.00           C+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   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Value	Source
5-L-Glutamyl-L-alanine	ChEBI
gamma-L-Glutamyl-L-alanine	ChEBI
L-gamma-Glu-L-ala	ChEBI
N-L-gamma-Glutamyl-L-alanine	ChEBI
g-L-Glutamyl-L-alanine	Generator
Γ-L-glutamyl-L-alanine	Generator
L-g-Glu-L-ala	Generator
L-Γ-glu-L-ala	Generator
N-L-g-Glutamyl-L-alanine	Generator
N-L-Γ-glutamyl-L-alanine	Generator
g-Glutamylalanine	Generator
Γ-glutamylalanine	Generator
Γ-glu-ala	HMDB
Γ-L-glu-L-ala	HMDB
L-Γ-glutamyl-L-alanine	HMDB
N-Γ-glutamylalanine	HMDB
N-L-Γ-glutamylalanine	HMDB
gamma-Glu-ala	HMDB
gamma-L-Glu-L-ala	HMDB
L-gamma-Glutamyl-L-alanine	HMDB
N-gamma-Glutamylalanine	HMDB
N-L-gamma-Glutamylalanine	HMDB
5-L-Glutamylalanine	HMDB
g-Glu-ala	HMDB
N-Γ-L-glutamyl-L-alanine	HMDB
N-gamma-L-Glutamyl-L-alanine	HMDB
gamma-Glutamylalanine	HMDB, ChEBI

Chemical Formula

C₈H₁₄N₂O₅

Average Mass

218.2072 Da

Monoisotopic Mass

218.09027 Da

IUPAC Name

(2S)-2-amino-4-{[(1S)-1-carboxyethyl]carbamoyl}butanoic acid

Traditional Name

g-glu-ala

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C8H14N2O5/c1-4(7(12)13)10-6(11)3-2-5(9)8(14)15/h4-5H,2-3,9H2,1H3,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1

InChI Key

WQXXXVRAFAKQJM-WHFBIAKZSA-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

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Annona squamosa	Plant	KNApSAcK
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dietes iridioides	LOTUS Database	35616633
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

gamma-glutamylalanine (CHEBI:50619 )

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	-3.4	ALOGPS
logP	-3.8	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	1.93	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	48.59 m³·mol⁻¹	ChemAxon
Polarizability	20.94 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

HMDB0006248

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023860

KNApSAcK ID

Not Available

Chemspider ID

389104

KEGG Compound ID

C03740

BioCyc ID

Not Available

BiGG ID

1446127

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440103

PDB ID

Not Available

ChEBI ID

50619

Good Scents ID

Not Available

References

General References

York MJ, Crossley MJ, Hyslop SJ, Fisher ML, Kuchel PW: gamma-Glutamylcyclotransferase: inhibition by D-beta-aminoglutaryl-L-alanine and analysis of the solvent kinetic isotope effect. Eur J Biochem. 1989 Sep 1;184(1):97-101. doi: 10.1111/j.1432-1033.1989.tb14994.x. [PubMed:2570694 ]
MORRIS CJ, THOMPSON JF, ASEN S: THE IDENTIFICATION OF GAMMA-L-GLUTAMYL-L-ALANINE AND GAMMA-L-GLUTAMYL-L-VALINE FROM IRIS LEAF TISSUE. J Biol Chem. 1964 Jun;239:1833-5. [PubMed:14213360 ]

Showing NP-Card for 5-L-Glutamyl-L-alanine (NP0085720)

MOL for NP0085720 (5-L-Glutamyl-L-alanine)

3D MOL for NP0085720 (5-L-Glutamyl-L-alanine)

3D SDF for NP0085720 (5-L-Glutamyl-L-alanine)

3D-SDF for NP0085720 (5-L-Glutamyl-L-alanine)

PDB for NP0085720 (5-L-Glutamyl-L-alanine)

3D PDB for NP0085720 (5-L-Glutamyl-L-alanine)

SMILES for NP0085720 (5-L-Glutamyl-L-alanine)

INCHI for NP0085720 (5-L-Glutamyl-L-alanine)

Structure for NP0085720 (5-L-Glutamyl-L-alanine)

3D Structure for NP0085720 (5-L-Glutamyl-L-alanine)