NP-MRD: Showing NP-Card for Glutamylserine (NP0136451)

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Record Information

Version

2.0

Created at

2022-05-12 15:14:52 UTC

Updated at

2022-05-12 15:14:53 UTC

NP-MRD ID

NP0136451

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glutamylserine

Description

Glutamylserine, also known as alpha-glu-ser or E-S, 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 dipeptidGlutamylserine are known to have physiological or cell-signaling effects although most are simply short-lived intermediatGlutamylserine on their way to specific amino acid degradation pathways following further proteolysis. Glutamylserine is a very strong basic compound (based on its pKa). Glutamylserine is a dipeptide composed of glutamate and serine, and is a proteolytic breakdown product of larger proteins. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Glutamylserine is found in Trypanosoma brucei. Glutamylserine was first documented in 1965 (PMID: 5867340). Glutamylserine is an incomplete breakdown product of protein digestion or protein catabolism.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 29  0  0  0  0  0  0  0  0999 V2000
   -0.8960   -1.7694   -0.3487 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1136   -0.4076   -0.7546 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1506    0.2763    0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4859   -0.4259    0.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4588    0.3057    0.9146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4551    0.1398    2.1607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3644    1.1676    0.3434 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1533    0.3495   -0.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1436    1.5611   -1.0165 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3578   -0.2574   -0.2448 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5748    0.5103   -0.1850 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1594    0.5811    1.2049 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319   -0.7214    1.6118 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6087   -0.0699   -1.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3406   -1.0951   -1.7359 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8447    0.5454   -1.1344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1454   -2.1913   -0.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7614   -2.3521   -0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4939   -0.4086   -1.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8324    0.2502    1.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2613    1.3254   -0.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8471   -0.4554   -1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3342   -1.4710    0.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1107    1.9202   -0.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3761   -1.2612    0.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3956    1.5480   -0.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4994    1.0841    1.9303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1073    1.1372    1.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7150   -1.2897    0.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0026    1.4741   -1.4756 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  7  1  0
  5  6  2  0
  2  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 16  1  0
 14 15  2  0
  1 17  1  0
  1 18  1  0
  2 19  1  6
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  7 24  1  0
 10 25  1  0
 11 26  1  6
 12 27  1  0
 12 28  1  0
 13 29  1  0
 16 30  1  0
M  END


  Mrv1652304062013402D          

 16 15  0  0  0  0            999 V2000
 2501.7850 2500.0010    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2501.0710 2499.5877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3570 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6429 2499.5877    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2498.9289 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2149 2499.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.5009 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.7869 2499.5877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.5009 2500.8255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6429 2498.7633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3570 2500.8255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4990 2499.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.2130 2500.0010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4990 2498.7633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7850 2500.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4990 2501.2366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 12  1  0  0  0  0
  1 15  1  1  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
  4 10  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136451

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H14N2O6/c9-4(1-2-6(12)13)7(14)10-5(3-11)8(15)16/h4-5,11H,1-3,9H2,(H,10,14)(H,12,13)(H,15,16)/t4-,5-/m0/s1

> <INCHI_KEY>
UQHGAYSULGRWRG-WHFBIAKZSA-N

> <FORMULA>
C8H14N2O6

> <MOLECULAR_WEIGHT>
234.208

> <EXACT_MASS>
234.085186179

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
21.684350549630484

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-3.55

> <JCHEM_LOGP>
-5.122600711260628

> <ALOGPS_LOGS>
-1.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.945593981999139

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1121955815753095

> <JCHEM_PKA_STRONGEST_BASIC>
8.44954048473961

> <JCHEM_POLAR_SURFACE_AREA>
149.95

> <JCHEM_REFRACTIVITY>
50.128800000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.37e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-4-amino-4-{[(1S)-1-carboxy-2-hydroxyethyl]carbamoyl}butanoic 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    4669.9994666.669   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4668.6664665.897   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4667.3334666.669   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4666.0004665.897   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4664.6674666.669   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4663.3344665.897   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4662.0024666.669   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    4660.6694665.897   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    4662.0024668.208   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0    4666.0004664.358   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0    4667.3334668.208   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    4671.3314665.897   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    4672.6644666.669   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    4671.3314664.358   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    4669.9994668.208   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    4671.3314668.975   0.000  0.00  0.00           O+0
CONECT    1    2   12   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    4                                                            
CONECT   11    3                                                            
CONECT   12    1   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    1   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

View in JSmol

Synonyms

Value	Source
alpha-Glu-ser	ChEBI
alpha-Glutamylserine	ChEBI
E-S	ChEBI
ES	ChEBI
L-Glu-L-ser	ChEBI
a-Glu-ser	Generator
Α-glu-ser	Generator
a-Glutamylserine	Generator
Α-glutamylserine	Generator
e-S Dipeptide	HMDB
ES dipeptide	HMDB
Glu-ser	HMDB
Glutamate serine dipeptide	HMDB
Glutamate-serine dipeptide	HMDB
L-Glutamyl-L-serine	HMDB
Α-L-glu-L-ser	HMDB
Α-L-glutamyl-L-serine	HMDB
L-Α-glutamyl-L-serine	HMDB
N-Α-glutamylserine	HMDB
N-Α-L-glutamyl-L-serine	HMDB
N-L-Α-glutamylserine	HMDB
N-L-Α-glutamyl-L-serine	HMDB
alpha-L-Glu-L-ser	HMDB
alpha-L-Glutamyl-L-serine	HMDB
L-alpha-Glutamyl-L-serine	HMDB
N-alpha-Glutamylserine	HMDB
N-alpha-L-Glutamyl-L-serine	HMDB
N-L-alpha-Glutamylserine	HMDB
N-L-alpha-Glutamyl-L-serine	HMDB
N-Glutamylserine	HMDB
N-L-Glutamyl-L-serine	HMDB
Glutamyl-serine	HMDB
Glutamic acid serine dipeptide	HMDB
Glutamic acid-serine dipeptide	HMDB
Glutamylserine	HMDB, ChEBI

Chemical Formula

C₈H₁₄N₂O₆

Average Mass

234.2080 Da

Monoisotopic Mass

234.08519 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C8H14N2O6/c9-4(1-2-6(12)13)7(14)10-5(3-11)8(15)16/h4-5,11H,1-3,9H2,(H,10,14)(H,12,13)(H,15,16)/t4-,5-/m0/s1

InChI Key

UQHGAYSULGRWRG-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
Trypanosoma brucei	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
Glutamic acid or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Serine or derivatives
Alpha-amino acid or derivatives
Amino fatty acid
Beta-hydroxy acid
Hydroxy fatty acid
Fatty acid
Hydroxy acid
Fatty acyl
N-acyl-amine
Fatty amide
Dicarboxylic acid or derivatives
Amino acid or derivatives
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Carboxylic acid
Primary amine
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Alcohol
Amine
Primary aliphatic amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:73509 )

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	-3.6	ALOGPS
logP	-5.1	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	3.11	ChemAxon
pKa (Strongest Basic)	8.45	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	149.95 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	50.13 m³·mol⁻¹	ChemAxon
Polarizability	21.68 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

HMDB0028828

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5363587

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6995653

PDB ID

Not Available

ChEBI ID

73509

Good Scents ID

Not Available

References

General References

Kanazawa A, Kakimoto Y, Nakajima T, Sano I: Identification of gamma-glutamylserine, gamma-glutamylalanine, gamma-glutamylvaline and S-methylglutathione of bovine brain. Biochim Biophys Acta. 1965 Nov 15;111(1):90-5. doi: 10.1016/0304-4165(65)90475-7. [PubMed:5867340 ]

Showing NP-Card for Glutamylserine (NP0136451)

MOL for NP0136451 (Glutamylserine)

3D MOL for NP0136451 (Glutamylserine)

3D SDF for NP0136451 (Glutamylserine)

3D-SDF for NP0136451 (Glutamylserine)

PDB for NP0136451 (Glutamylserine)

3D PDB for NP0136451 (Glutamylserine)

SMILES for NP0136451 (Glutamylserine)

INCHI for NP0136451 (Glutamylserine)

Structure for NP0136451 (Glutamylserine)

3D Structure for NP0136451 (Glutamylserine)