NP-MRD: Showing NP-Card for Glutaminylglycine (NP0136427)

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Record Information

Version

2.0

Created at

2022-05-12 15:14:16 UTC

Updated at

2022-05-12 15:14:16 UTC

NP-MRD ID

NP0136427

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glutaminylglycine

Description

Glutaminylglycine, also known as L-GLN-gly or QG, 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. Glutaminylglycine is a very strong basic compound (based on its pKa). Glutaminylglycine was first documented in 1977 (PMID: 21685). It is an incomplete breakdown product of protein digestion or protein catabolism (PMID: 23218487) (PMID: 21469233) (PMID: 6113588) (PMID: 19675894) (PMID: 21193394) (PMID: 9193708).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304062013362D          

 14 13  0  0  0  0            999 V2000
 2500.3574 2500.2058    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2499.6425 2499.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9276 2500.2058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2124 2499.7941    0.0000 C   0  0  0  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 2499.7941    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
 2499.6425 2498.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0723 2499.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7875 2500.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.5024 2499.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.2173 2500.2058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2502.5024 2498.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3574 2501.0315    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  0  0  0  0
  1 14  1  1  0  0  0
  2  3  1  0  0  0  0
  2  8  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  7  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136427

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H13N3O4/c8-4(1-2-5(9)11)7(14)10-3-6(12)13/h4H,1-3,8H2,(H2,9,11)(H,10,14)(H,12,13)/t4-/m0/s1

> <INCHI_KEY>
JEFZIKRIDLHOIF-BYPYZUCNSA-N

> <FORMULA>
C7H13N3O4

> <MOLECULAR_WEIGHT>
203.198

> <EXACT_MASS>
203.090605911

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
19.33153001769097

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2S)-2-amino-4-carbamoylbutanamido]acetic acid

> <ALOGPS_LOGP>
-3.31

> <JCHEM_LOGP>
-5.10872370691333

> <ALOGPS_LOGS>
-1.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.161750420662951

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.532645531445243

> <JCHEM_PKA_STRONGEST_BASIC>
8.22597768419463

> <JCHEM_POLAR_SURFACE_AREA>
135.51000000000002

> <JCHEM_REFRACTIVITY>
45.91340000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.55e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S)-2-amino-4-carbamoylbutanamido]acetic 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    4667.3344667.051   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4665.9994666.282   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    4664.6654667.051   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    4663.3304666.282   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4661.9954667.051   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    4660.6614666.282   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    4661.9954668.592   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    4665.9994664.741   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    4668.6684666.282   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    4670.0034667.051   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    4671.3384666.282   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0    4672.6724667.051   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0    4671.3384664.741   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0    4667.3344668.592   0.000  0.00  0.00           N+0
CONECT    1    2    9   14                                                  
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    2                                                            
CONECT    9    1   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    1                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol

Synonyms

Value	Source
Glutaminyl-glycine	ChEBI
L-GLN-Gly	ChEBI
QG	ChEBI
NSC 350592	HMDB
GLN-Gly	HMDB
L-Glutaminylglycine	HMDB
Glutamine glycine dipeptide	HMDB
Glutamine-glycine dipeptide	HMDB
Q-g Dipeptide	HMDB
QG Dipeptide	HMDB
N-L-Glutaminylglycine	HMDB
N-Glutaminylglycine	HMDB
Glutaminylglycine	HMDB, ChEBI

Chemical Formula

C₇H₁₃N₃O₄

Average Mass

203.1980 Da

Monoisotopic Mass

203.09061 Da

IUPAC Name

2-[(2S)-2-amino-4-carbamoylbutanamido]acetic acid

Traditional Name

[(2S)-2-amino-4-carbamoylbutanamido]acetic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C7H13N3O4/c8-4(1-2-5(9)11)7(14)10-3-6(12)13/h4H,1-3,8H2,(H2,9,11)(H,10,14)(H,12,13)/t4-/m0/s1

InChI Key

JEFZIKRIDLHOIF-BYPYZUCNSA-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
Glutamine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Fatty amide
N-acyl-amine
Fatty acyl
Amino acid or derivatives
Carboxamide group
Carboxylic acid salt
Amino acid
Primary carboxylic acid amide
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Organonitrogen compound
Hydrocarbon derivative
Amine
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Primary amine
Carbonyl group
Organic zwitterion
Organic salt
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:73848 )

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	-3.3	ALOGPS
logP	-5.1	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.53	ChemAxon
pKa (Strongest Basic)	8.23	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	135.51 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	45.91 m³·mol⁻¹	ChemAxon
Polarizability	19.33 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

HMDB0028797

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5360815

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6992690

PDB ID

Not Available

ChEBI ID

73848

Good Scents ID

Not Available

References

General References

Arai T, Noguchi A, Takano E, Kino K: Application of protein N-terminal amidase in enzymatic synthesis of dipeptides containing acidic amino acids specifically at the N-terminus. J Biosci Bioeng. 2013 Apr;115(4):382-7. doi: 10.1016/j.jbiosc.2012.10.024. Epub 2012 Dec 4. [PubMed:23218487 ]
Kitaoka M, Tsuruda Y, Tanaka Y, Goto M, Mitsumori M, Hayashi K, Hiraishi Y, Miyawaki K, Noji S, Kamiya N: Transglutaminase-mediated synthesis of a DNA-(enzyme)n probe for highly sensitive DNA detection. Chemistry. 2011 May 2;17(19):5387-92. doi: 10.1002/chem.201003744. Epub 2011 Apr 5. [PubMed:21469233 ]
Abe T, Chung SI, DiAugustine RP, Folk JE: Rabbit liver transglutaminase: physical, chemical, and catalytic properties. Biochemistry. 1977 Dec 13;16(25):5495-501. doi: 10.1021/bi00644a016. [PubMed:21685 ]
Inoue M, Morino Y: Inactivation of renal gamma-glutamyl transferase by 6-diazo-5-oxo-L-norleucylglycine, an inactive precursor of affinity-labeling reagent. Proc Natl Acad Sci U S A. 1981 Jan;78(1):46-9. doi: 10.1073/pnas.78.1.46. [PubMed:6113588 ]
Kamiya N, Abe H, Goto M, Tsuji Y, Jikuya H: Fluorescent substrates for covalent protein labeling catalyzed by microbial transglutaminase. Org Biomol Chem. 2009 Sep 7;7(17):3407-12. doi: 10.1039/b904046c. Epub 2009 Jun 30. [PubMed:19675894 ]
Yang MT, Chang CH, Wang JM, Wu TK, Wang YK, Chang CY, Li TT: Crystal structure and inhibition studies of transglutaminase from Streptomyces mobaraense. J Biol Chem. 2011 Mar 4;286(9):7301-7. doi: 10.1074/jbc.M110.203315. Epub 2010 Dec 29. [PubMed:21193394 ]
Pasternack R, Laurent HP, Ruth T, Kaiser A, Schon N, Fuchsbauer HL: A fluorescent substrate of transglutaminase for detection and characterization of glutamine acceptor compounds. Anal Biochem. 1997 Jun 15;249(1):54-60. doi: 10.1006/abio.1997.2139. [PubMed:9193708 ]
Suchanek G, Kreil G: Translation of melittin messenger RNA in vitro yields a product terminating with glutaminylglycine rather than with glutaminamide. Proc Natl Acad Sci U S A. 1977 Mar;74(3):975-8. doi: 10.1073/pnas.74.3.975. [PubMed:265590 ]
Kamiya N, Abe H: New fluorescent substrates of microbial transglutaminase and its application to peptide tag-directed covalent protein labeling. Methods Mol Biol. 2011;751:81-94. doi: 10.1007/978-1-61779-151-2_7. [PubMed:21674327 ]

Showing NP-Card for Glutaminylglycine (NP0136427)

MOL for NP0136427 (Glutaminylglycine)

3D MOL for NP0136427 (Glutaminylglycine)

3D SDF for NP0136427 (Glutaminylglycine)

3D-SDF for NP0136427 (Glutaminylglycine)

PDB for NP0136427 (Glutaminylglycine)

3D PDB for NP0136427 (Glutaminylglycine)

SMILES for NP0136427 (Glutaminylglycine)

INCHI for NP0136427 (Glutaminylglycine)

Structure for NP0136427 (Glutaminylglycine)

3D Structure for NP0136427 (Glutaminylglycine)