NP-MRD: Showing NP-Card for gamma-Glutamylthreonine (NP0136728)

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Record Information

Version

2.0

Created at

2022-05-12 15:21:58 UTC

Updated at

2022-05-12 15:21:58 UTC

NP-MRD ID

NP0136728

Secondary Accession Numbers

None

Natural Product Identification

Common Name

gamma-Glutamylthreonine

Description

Gamma-Glutamylthreonine, also known as L-gamma-glu-L-THR or γ-L-glutamyl-L-threonine, 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-Glutamylthreonine is a dipeptide composed of gamma-glutamate and threonine, and is a proteolytic breakdown product of larger proteins. 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. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Gamma-Glutamylthreonine is a very strong basic compound (based on its pKa). Gamma-Glutamylthreonine is an incomplete breakdown product of protein digestion or protein catabolism.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 32  0  0  0  0  0  0  0  0999 V2000
   -3.9661   -0.5944    1.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691   -1.2869    0.0444 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8668   -1.8427   -0.9709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0086   -0.3996   -0.5456 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2258    0.1391    0.5437 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1671   -0.1530    0.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6575   -0.8893   -0.2254 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9887    0.3834    1.7591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4373    0.1505    1.5933 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1214    0.7957    0.4411 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6817    0.4691   -0.8611 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5885    0.4607    0.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1378   -0.0191   -0.4693 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2798    0.6849    1.7339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5295    0.7110   -1.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3284    1.9265   -1.1013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3221    0.4141   -2.4482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5482   -0.7321    2.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9967    0.4972    0.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9828   -1.0475    1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5966   -2.1500    0.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4618   -2.6981   -1.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3414   -1.0171   -1.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6662    0.7540    1.2695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6008   -0.1100    2.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7165    1.4614    1.8616 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6074   -0.9723    1.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9359    0.4315    2.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0860    1.9159    0.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4015    1.2666   -1.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2185   -0.2694   -1.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2753    0.8931    1.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9914    0.8271   -3.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 14  1  0
 12 13  2  0
  4 15  1  0
 15 17  1  0
 15 16  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  1
  3 22  1  0
  4 23  1  6
  5 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  1
 11 30  1  0
 11 31  1  0
 14 32  1  0
 17 33  1  0
M  END


  Mrv1652304062014292D          

 17 16  0  0  0  0            999 V2000
 2498.5911 2500.3796    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2499.3062 2500.7913    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0212 2500.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7359 2500.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4509 2500.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1659 2500.7913    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2502.8810 2500.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.5956 2500.7913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.8810 2499.5539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1659 2501.6169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0212 2499.5539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8762 2500.7913    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2497.1614 2500.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8762 2501.6169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2498.5911 2499.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8762 2499.1401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.3062 2499.1401    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  6  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  6  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  1  1  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136728

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H16N2O6/c1-4(12)7(9(16)17)11-6(13)3-2-5(10)8(14)15/h4-5,7,12H,2-3,10H2,1H3,(H,11,13)(H,14,15)(H,16,17)/t4-,5+,7+/m1/s1

> <INCHI_KEY>
GWNXFCYUJXASDX-ZDLURKLDSA-N

> <FORMULA>
C9H16N2O6

> <MOLECULAR_WEIGHT>
248.235

> <EXACT_MASS>
248.100836243

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
23.28563342735822

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-3.40

> <JCHEM_LOGP>
-4.457135456913003

> <ALOGPS_LOGS>
-1.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.728311276780793

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.887340478917678

> <JCHEM_PKA_STRONGEST_BASIC>
9.311864183674457

> <JCHEM_POLAR_SURFACE_AREA>
149.95

> <JCHEM_REFRACTIVITY>
54.5476

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.99e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-4-{[(1S,2R)-1-carboxy-2-hydroxypropyl]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    4664.0374667.375   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4665.3724668.144   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4666.7064667.375   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4668.0404668.144   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4669.3754667.375   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4670.7104668.144   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4672.0444667.375   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    4673.3784668.144   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    4672.0444665.834   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0    4670.7104669.685   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0    4666.7064665.834   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    4662.7024668.144   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4661.3684667.375   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    4662.7024669.685   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    4664.0374665.834   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    4662.7024665.062   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    4665.3724665.062   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                                                       
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   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    1   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

View in JSmol

Synonyms

Value	Source
(2S)-2-Amino-5-{[(1S,2R)-1-carboxy-2-hydroxypropyl]amino}-5-oxopentanoic acid	ChEBI
L-gamma-Glu-L-THR	ChEBI
(2S)-2-Amino-5-{[(1S,2R)-1-carboxy-2-hydroxypropyl]amino}-5-oxopentanoate	Generator
L-g-Glu-L-THR	Generator
L-Γ-glu-L-THR	Generator
g-Glutamylthreonine	Generator
Γ-glutamylthreonine	Generator
g-Glu-THR	HMDB
Γ-glu-THR	HMDB
Γ-L-glu-L-THR	HMDB
Γ-L-glutamyl-L-threonine	HMDB
L-Γ-glutamyl-L-threonine	HMDB
N-Γ-glutamylthreonine	HMDB
N-L-Γ-glutamylthreonine	HMDB
N-L-Γ-glutamyl-L-threonine	HMDB
gamma-Glu-THR	HMDB
gamma-L-Glu-L-THR	HMDB
gamma-L-Glutamyl-L-threonine	HMDB
L-gamma-Glutamyl-L-threonine	HMDB
N-gamma-Glutamylthreonine	HMDB
N-L-gamma-Glutamylthreonine	HMDB
N-L-gamma-Glutamyl-L-threonine	HMDB
N-Γ-L-glutamyl-L-threonine	HMDB
N-gamma-L-Glutamyl-L-threonine	HMDB
gamma-Glutamylthreonine	HMDB, ChEBI

Chemical Formula

C₉H₁₆N₂O₆

Average Mass

248.2350 Da

Monoisotopic Mass

248.10084 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C9H16N2O6/c1-4(12)7(9(16)17)11-6(13)3-2-5(10)8(14)15/h4-5,7,12H,2-3,10H2,1H3,(H,11,13)(H,14,15)(H,16,17)/t4-,5+,7+/m1/s1

InChI Key

GWNXFCYUJXASDX-ZDLURKLDSA-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 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
Beta-hydroxy acid
Short-chain hydroxy acid
Hydroxy acid
N-acyl-amine
Fatty amide
Dicarboxylic acid or derivatives
Fatty acyl
Fatty acid
Amino acid
Secondary alcohol
Secondary carboxylic acid amide
Carboxamide group
Amino acid or derivatives
Carboxylic acid
Organonitrogen compound
Organooxygen compound
Primary amine
Alcohol
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	-3.4	ALOGPS
logP	-4.5	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	1.89	ChemAxon
pKa (Strongest Basic)	9.31	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	54.55 m³·mol⁻¹	ChemAxon
Polarizability	23.29 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

HMDB0029159

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

29273165

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53861142

PDB ID

Not Available

ChEBI ID

133747

Good Scents ID

Not Available

References

General References

Showing NP-Card for gamma-Glutamylthreonine (NP0136728)

MOL for NP0136728 (gamma-Glutamylthreonine)

3D MOL for NP0136728 (gamma-Glutamylthreonine)

3D SDF for NP0136728 (gamma-Glutamylthreonine)

3D-SDF for NP0136728 (gamma-Glutamylthreonine)

PDB for NP0136728 (gamma-Glutamylthreonine)

3D PDB for NP0136728 (gamma-Glutamylthreonine)

SMILES for NP0136728 (gamma-Glutamylthreonine)

INCHI for NP0136728 (gamma-Glutamylthreonine)

Structure for NP0136728 (gamma-Glutamylthreonine)

3D Structure for NP0136728 (gamma-Glutamylthreonine)