NP-MRD: Showing NP-Card for gamma-Glutamyllysine (NP0136725)

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Record Information

Version

2.0

Created at

2022-05-12 15:21:53 UTC

Updated at

2022-05-12 15:21:53 UTC

NP-MRD ID

NP0136725

Secondary Accession Numbers

None

Natural Product Identification

Common Name

gamma-Glutamyllysine

Description

Gamma-Glutamyllysine, also known as ge-K dipeptide or gglu-lys, 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. 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. Gamma-Glutamyllysine is a dipeptide composed of gamma-glutamate and lysine, and is a proteolytic breakdown product of larger proteins. Gamma-Glutamyllysine is a very strong basic compound (based on its pKa). Gamma-Glutamyllysine is an incomplete breakdown product of protein digestion or protein catabolism. gamma-Glutamyllysine is found in Lentinula edodes. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 39  0  0  0  0  0  0  0  0999 V2000
   -5.2489    1.0822   -1.6373 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5060   -0.1101   -0.8508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2217   -0.8929   -0.6812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2491    0.0426    0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9324   -0.6003    0.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0048    0.3708    0.9843 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2976   -0.2794    1.2036 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4153    0.2546    0.4987 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3049    1.2380   -0.2783 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7785   -0.3405    0.6574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7316    0.4336   -0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1507   -0.0298   -0.1526 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8941    0.8673   -1.0636 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2708   -1.4055   -0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8944   -1.6544   -1.7400 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7305   -2.4917    0.0053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5204    0.8511    2.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8279    0.6007    3.3308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6729    1.5491    2.5023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2783    1.9568   -1.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0472    1.2204   -2.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8272    0.2446    0.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3036   -0.6968   -1.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8375   -1.1496   -1.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4319   -1.7906   -0.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7409    0.2459    1.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1256    0.9172   -0.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4647   -1.0354   -0.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0588   -1.4616    0.9998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8357    1.1979    0.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4279   -1.0903    1.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0336   -0.3247    1.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7300   -1.4050    0.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6325    1.5074    0.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3204    0.4070   -1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5688    0.0962    0.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9149    0.7181   -0.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7003    1.8456   -0.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1638   -3.1490   -0.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8248    2.2604    3.1759 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  1  0
  6  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
  6 17  1  0
 17 19  1  0
 17 18  2  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  6
  7 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  1
 13 37  1  0
 13 38  1  0
 16 39  1  0
 19 40  1  0
M  END


  Mrv1652304062014282D          

 19 18  0  0  0  0            999 V2000
 2499.6427 2499.5885    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2499.6427 2500.4135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3572 2500.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0716 2500.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7861 2500.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.5005 2500.4135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2503.2150 2500.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.9294 2500.4135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2503.2150 2501.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.5005 2499.5885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3572 2501.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9283 2499.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2138 2499.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.4994 2499.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.7849 2499.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.0705 2499.1749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3572 2499.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0716 2499.5885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3572 2498.3499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  1 12  1  0  0  0  0
  1 17  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 11  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 10  1  1  0  0  0
  7  8  1  0  0  0  0
  7  9  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
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136725

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H21N3O5/c12-6-2-1-3-8(11(18)19)14-9(15)5-4-7(13)10(16)17/h7-8H,1-6,12-13H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-/m0/s1

> <INCHI_KEY>
LNLLNTMHVMIMOG-YUMQZZPRSA-N

> <FORMULA>
C11H21N3O5

> <MOLECULAR_WEIGHT>
275.305

> <EXACT_MASS>
275.148120788

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.048072148888366

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-6-amino-2-[(4S)-4-amino-4-carboxybutanamido]hexanoic acid

> <ALOGPS_LOGP>
-3.99

> <JCHEM_LOGP>
-6.127313964934809

> <ALOGPS_LOGS>
-1.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.7428151634583515

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8904827090391305

> <JCHEM_PKA_STRONGEST_BASIC>
10.257667356449648

> <JCHEM_POLAR_SURFACE_AREA>
155.73999999999998

> <JCHEM_REFRACTIVITY>
65.8973

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-6-amino-2-[(4S)-4-amino-4-carboxybutanamido]hexanoic 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  C   UNK     0    4666.0004665.899   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4666.0004667.439   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4667.3334668.207   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4668.6674667.439   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4670.0014668.207   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4671.3344667.439   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4672.6684668.207   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    4674.0024667.439   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    4672.6684669.747   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0    4671.3344665.899   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0    4667.3334669.747   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    4664.6664665.126   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4663.3324665.899   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4661.9994665.126   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4660.6654665.899   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0    4659.3324665.126   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0    4667.3334665.126   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0    4668.6674665.899   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0    4667.3334663.586   0.000  0.00  0.00           O+0
CONECT    1    2   12   17                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6                                                            
CONECT   11    3                                                            
CONECT   12    1   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17    1   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

View in JSmol

Synonyms

Value	Source
g-Glutamyllysine	Generator
Γ-glutamyllysine	Generator
gamma-Glutamate lysine dipeptide	HMDB
gamma-Glutamate-lysine dipeptide	HMDB
GE-K dipeptide	HMDB
GEK dipeptide	HMDB
GGlu-lys	HMDB
L-gamma-Glutamyl-L-lysine	HMDB
Γ-glu-lys	HMDB
Γ-L-glu-L-lys	HMDB
Γ-L-glutamyl-L-lysine	HMDB
L-Γ-glutamyl-L-lysine	HMDB
N2-Γ-glutamyllysine	HMDB
N2-L-Γ-glutamyllysine	HMDB
N2-L-Γ-glutamyl-L-lysine	HMDB
gamma-Glu-lys	HMDB
gamma-L-Glu-L-lys	HMDB
gamma-L-Glutamyl-L-lysine	HMDB
N2-gamma-Glutamyllysine	HMDB
N2-L-gamma-Glutamyllysine	HMDB
N2-L-gamma-Glutamyl-L-lysine	HMDB
N2-Γ-L-glutamyl-L-lysine	HMDB
N2-gamma-L-Glutamyl-L-lysine	HMDB
gamma-Glutamyllysine	HMDB
(2S)-6-Amino-2-{[(4S)-4-amino-4-carboxy-1-hydroxybutylidene]amino}hexanoate	Generator

Chemical Formula

C₁₁H₂₁N₃O₅

Average Mass

275.3050 Da

Monoisotopic Mass

275.14812 Da

IUPAC Name

(2S)-6-amino-2-[(4S)-4-amino-4-carboxybutanamido]hexanoic acid

Traditional Name

(2S)-6-amino-2-[(4S)-4-amino-4-carboxybutanamido]hexanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H21N3O5/c12-6-2-1-3-8(11(18)19)14-9(15)5-4-7(13)10(16)17/h7-8H,1-6,12-13H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-/m0/s1

InChI Key

LNLLNTMHVMIMOG-YUMQZZPRSA-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
Lentinus edodes	LOTUS Database	35616633

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
N-acyl-l-alpha-amino acid
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Medium-chain fatty acid
Amino fatty acid
Fatty acid
Dicarboxylic acid or derivatives
Fatty amide
N-acyl-amine
Fatty acyl
Carboxamide group
Secondary carboxylic acid amide
Amino acid
Amino acid or derivatives
Carboxylic acid
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
Organic nitrogen compound
Primary aliphatic 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	-4	ALOGPS
logP	-6.1	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	1.89	ChemAxon
pKa (Strongest Basic)	10.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.74 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	65.9 m³·mol⁻¹	ChemAxon
Polarizability	28.05 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

HMDB0029154

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58747

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

65254

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for gamma-Glutamyllysine (NP0136725)

MOL for NP0136725 (gamma-Glutamyllysine)

3D MOL for NP0136725 (gamma-Glutamyllysine)

3D SDF for NP0136725 (gamma-Glutamyllysine)

3D-SDF for NP0136725 (gamma-Glutamyllysine)

PDB for NP0136725 (gamma-Glutamyllysine)

3D PDB for NP0136725 (gamma-Glutamyllysine)

SMILES for NP0136725 (gamma-Glutamyllysine)

INCHI for NP0136725 (gamma-Glutamyllysine)

Structure for NP0136725 (gamma-Glutamyllysine)

3D Structure for NP0136725 (gamma-Glutamyllysine)