NP-MRD: Showing NP-Card for Glutaminylcysteine (NP0136424)

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Record Information

Version

2.0

Created at

2022-05-12 15:14:11 UTC

Updated at

2022-05-12 15:14:11 UTC

NP-MRD ID

NP0136424

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glutaminylcysteine

Description

Glutaminylcysteine, also known as Q-C dipeptide or GLN-cys, 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. Glutaminylcysteine is a very strong basic compound (based on its pKa). It is an incomplete breakdown product of protein digestion or protein catabolism.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 30  0  0  0  0  0  0  0  0999 V2000
    5.3462   -1.3203   -0.6778 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -0.8688   -0.8912 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5351   -0.9136   -2.0464 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1794   -0.3480    0.2117 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8418    0.0453   -0.3165 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9245    0.5910    0.7577 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7100   -0.4245    1.7940 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3698    0.9915    0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3395    1.8575   -0.7420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5842    0.4376    0.5812 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8773    0.7647    0.0638 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5705   -0.4503   -0.5522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5677   -1.1076   -1.9204 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7992    1.3034    1.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3691    1.4141    2.2546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0991    1.6940    0.8458 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9710   -0.7496   -0.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6522   -2.2255   -1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0944   -1.1559    0.9966 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7170    0.4819    0.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9890    0.8541   -1.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3740   -0.8267   -0.8129 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4227    1.4791    1.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5555   -0.4056    2.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7043   -1.3629    1.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5508   -0.2908    1.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7938    1.5359   -0.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7567   -1.2161    0.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5628   -0.1309   -0.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3028   -2.1289   -2.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4883    2.4761    1.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  6  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
  7 24  1  0
  7 25  1  0
  6 23  1  1
  5 21  1  0
  5 22  1  0
  4 19  1  0
  4 20  1  0
  1 17  1  0
  1 18  1  0
 10 26  1  0
 11 27  1  6
 12 28  1  0
 12 29  1  0
 13 30  1  0
 16 31  1  0
M  END


  Mrv1652304062013352D          

 16 15  0  0  0  0            999 V2000
 2502.0697 2500.2855    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2501.3557 2499.8722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.6416 2500.2855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.9274 2499.8722    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2499.2133 2500.2855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.4991 2499.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.7851 2500.2855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.0711 2499.8722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2497.7851 2501.1101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.9274 2499.0477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.6416 2501.1101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.7837 2499.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.4979 2500.2855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.7837 2499.0477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.0697 2501.1101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.7837 2501.5213    0.0000 S   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>
NP0136424

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H15N3O4S/c9-4(1-2-6(10)12)7(13)11-5(3-16)8(14)15/h4-5,16H,1-3,9H2,(H2,10,12)(H,11,13)(H,14,15)/t4-,5-/m0/s1

> <INCHI_KEY>
XIPZDANNDPMZGQ-WHFBIAKZSA-N

> <FORMULA>
C8H15N3O4S

> <MOLECULAR_WEIGHT>
249.29

> <EXACT_MASS>
249.078327149

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
23.98883548236788

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-[(2S)-2-amino-4-carbamoylbutanamido]-3-sulfanylpropanoic acid

> <ALOGPS_LOGP>
-2.89

> <JCHEM_LOGP>
-4.4914216870897565

> <ALOGPS_LOGS>
-1.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.055694990660584

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.523031033123993

> <JCHEM_PKA_STRONGEST_BASIC>
8.219142538870978

> <JCHEM_POLAR_SURFACE_AREA>
135.51000000000002

> <JCHEM_REFRACTIVITY>
58.1336

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(2S)-2-amino-4-carbamoylbutanamido]-3-sulfanylpropanoic 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    4670.5304667.200   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4669.1974666.428   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4667.8644667.200   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4666.5314666.428   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4665.1984667.200   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4663.8654666.428   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4662.5324667.200   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0    4661.1994666.428   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0    4662.5324668.739   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0    4666.5314664.889   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0    4667.8644668.739   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    4671.8634666.428   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    4673.1964667.200   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    4671.8634664.889   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    4670.5304668.739   0.000  0.00  0.00           C+0
HETATM   16  S   UNK     0    4671.8634669.506   0.000  0.00  0.00           S+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
GLN-Cys	HMDB
L-Glutaminyl-L-cysteine	HMDB
Glutaminyl-cysteine	HMDB
Glutamine cysteine dipeptide	HMDB
Glutamine-cysteine dipeptide	HMDB
Q-C Dipeptide	HMDB
QC Dipeptide	HMDB
L-GLN-L-Cys	HMDB
Glutaminylcysteine	HMDB
(2R)-2-{[(2S)-2-amino-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-3-sulfanylpropanoate	Generator
(2R)-2-{[(2S)-2-amino-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-3-sulphanylpropanoate	Generator
(2R)-2-{[(2S)-2-amino-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-3-sulphanylpropanoic acid	Generator

Chemical Formula

C₈H₁₅N₃O₄S

Average Mass

249.2900 Da

Monoisotopic Mass

249.07833 Da

IUPAC Name

(2R)-2-[(2S)-2-amino-4-carbamoylbutanamido]-3-sulfanylpropanoic acid

Traditional Name

(2R)-2-[(2S)-2-amino-4-carbamoylbutanamido]-3-sulfanylpropanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C8H15N3O4S/c9-4(1-2-6(10)12)7(13)11-5(3-16)8(14)15/h4-5,16H,1-3,9H2,(H2,10,12)(H,11,13)(H,14,15)/t4-,5-/m0/s1

InChI Key

XIPZDANNDPMZGQ-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

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-l-alpha-amino acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Cysteine or derivatives
Alpha-amino acid or derivatives
Fatty amide
Fatty acyl
N-acyl-amine
Amino acid or derivatives
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Primary carboxylic acid amide
Alkylthiol
Carboxylic acid
Monocarboxylic acid or derivatives
Primary amine
Organic nitrogen compound
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Organic oxygen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
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	-2.9	ALOGPS
logP	-4.5	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.52	ChemAxon
pKa (Strongest Basic)	8.22	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	135.51 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	58.13 m³·mol⁻¹	ChemAxon
Polarizability	23.99 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

HMDB0028794

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26944399

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54471413

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Glutaminylcysteine (NP0136424)

MOL for NP0136424 (Glutaminylcysteine)

3D MOL for NP0136424 (Glutaminylcysteine)

3D SDF for NP0136424 (Glutaminylcysteine)

3D-SDF for NP0136424 (Glutaminylcysteine)

PDB for NP0136424 (Glutaminylcysteine)

3D PDB for NP0136424 (Glutaminylcysteine)

SMILES for NP0136424 (Glutaminylcysteine)

INCHI for NP0136424 (Glutaminylcysteine)

Structure for NP0136424 (Glutaminylcysteine)

3D Structure for NP0136424 (Glutaminylcysteine)