NP-MRD: Showing NP-Card for Glutaminylleucine (NP0136430)

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Record Information

Version

2.0

Created at

2022-05-12 15:14:21 UTC

Updated at

2022-05-12 15:14:21 UTC

NP-MRD ID

NP0136430

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glutaminylleucine

Description

Glutaminylleucine, also known as Q-L dipeptide or L-GLN-L-leu, 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. Glutaminylleucine 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

 39 38  0  0  0  0  0  0  0  0999 V2000
   -2.9437    0.3653   -2.9105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8801    0.4881   -1.3991 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9379    1.9435   -1.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6383   -0.1756   -0.9000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4817   -0.1061    0.5866 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2417   -0.7860    0.9168 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8368   -0.0764    1.4934 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7883    1.1527    1.7483 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0862   -0.7975    1.8177 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9762   -2.1747    1.4571 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2271   -0.1047    1.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9968   -0.1224   -0.3652 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1203    0.5615   -1.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1128    0.6652   -2.4636 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0613    1.0399   -0.4033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5969   -0.6874    1.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3547   -1.6398    2.1362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9039   -0.2699    1.2794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0099    0.4640   -3.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5212   -0.5872   -3.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3867    1.2276   -3.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7904   -0.0436   -1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2874    2.1200    0.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6404    2.5070   -1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9364    2.4028   -1.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6966   -1.2513   -1.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7750    0.3089   -1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3721    0.9737    0.8701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1642   -1.8064    0.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3255   -0.7384    2.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2676   -2.6569    2.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7960   -2.2736    0.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2772    0.9532    1.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1839   -0.5668    1.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0299    0.3450   -0.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9732   -1.1573   -0.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5885   -0.0400   -3.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6162    1.4262   -2.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7046   -0.8827    1.3312 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  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  5 16  1  0
 16 18  1  0
 16 17  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  1
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  1
  6 29  1  0
  9 30  1  1
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 18 39  1  0
M  END

      
  Mrv1652304062013362D          

 18 17  0  0  0  0            999 V2000
 2504.5197 2503.1287    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2504.5197 2503.9544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2505.2326 2504.3683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2505.9478 2503.9544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2505.2326 2505.1940    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2504.5197 2505.6056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.8050 2505.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.0901 2505.6056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.3750 2505.1940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2503.0901 2506.4313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2505.9478 2505.6056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2503.8050 2502.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.0901 2503.1287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.3729 2502.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.0901 2503.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2505.2347 2502.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2505.9499 2503.1287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2505.2347 2501.8915    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 16  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  6  0  0  0
  5  6  1  0  0  0  0
  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136430

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H21N3O4/c1-6(2)5-8(11(17)18)14-10(16)7(12)3-4-9(13)15/h6-8H,3-5,12H2,1-2H3,(H2,13,15)(H,14,16)(H,17,18)/t7-,8-/m0/s1

> <INCHI_KEY>
ARPVSMCNIDAQBO-YUMQZZPRSA-N

> <FORMULA>
C11H21N3O4

> <MOLECULAR_WEIGHT>
259.306

> <EXACT_MASS>
259.153206168

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.997296606280077

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.77

> <JCHEM_LOGP>
-3.285560702609918

> <ALOGPS_LOGS>
-1.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.715295394058689

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7779356185079145

> <JCHEM_PKA_STRONGEST_BASIC>
8.225671668304386

> <JCHEM_POLAR_SURFACE_AREA>
135.51

> <JCHEM_REFRACTIVITY>
64.0809

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-amino-4-carbamoylbutanamido]-4-methylpentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0    4675.1034672.507   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4675.1034674.048   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4676.4344674.821   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    4677.7694674.048   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    4676.4344676.362   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4675.1034677.130   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4673.7694676.362   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    4672.4354677.130   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0    4671.1004676.362   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0    4672.4354678.672   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0    4677.7694677.130   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0    4673.7694671.739   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4672.4354672.507   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4671.0964671.739   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4672.4354674.048   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    4676.4384671.739   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    4677.7734672.507   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0    4676.4384670.197   0.000  0.00  0.00           O+0
CONECT    1    2   12   16                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5                                                            
CONECT   12    1   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    1   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Value	Source
(2S)-2-[(2S)-2-Amino-4-carbamoylbutanamido]-4-methylpentanoic acid	ChEBI
(2S)-2-{[(2S)-2,5-diamino-5-oxopentanoyl]amino}-4-methylpentanoic acid	ChEBI
Glu-leu	ChEBI
Glutamine leucine dipeptide	ChEBI
Glutaminyl-leucine	ChEBI
L-GLN-L-Leu	ChEBI
N-L-Glutaminyl-L-leucine	ChEBI
Q-L	ChEBI
Q-L Dipeptide	ChEBI
QL	ChEBI
QL Dipeptide	ChEBI
(2S)-2-[(2S)-2-Amino-4-carbamoylbutanamido]-4-methylpentanoate	Generator
(2S)-2-{[(2S)-2,5-diamino-5-oxopentanoyl]amino}-4-methylpentanoate	Generator
GLN-Leu	HMDB
L-Glutaminyl-L-leucine	HMDB
N-Glutaminylleucine	HMDB
Glutamine-leucine dipeptide	HMDB
Glutaminylleucine	HMDB, ChEBI
(2S)-2-{[(2S)-2-amino-1-hydroxy-4-(C-hydroxycarbonimidoyl)butylidene]amino}-4-methylpentanoate	Generator

Chemical Formula

C₁₁H₂₁N₃O₄

Average Mass

259.3060 Da

Monoisotopic Mass

259.15321 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H21N3O4/c1-6(2)5-8(11(17)18)14-10(16)7(12)3-4-9(13)15/h6-8H,3-5,12H2,1-2H3,(H2,13,15)(H,14,16)(H,17,18)/t7-,8-/m0/s1

InChI Key

ARPVSMCNIDAQBO-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

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
Leucine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Alpha-amino acid or derivatives
Branched fatty acid
Methyl-branched fatty acid
N-acyl-amine
Fatty amide
Fatty acid
Fatty acyl
Primary carboxylic acid amide
Amino acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Primary aliphatic amine
Organooxygen compound
Primary amine
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Amine
Organic oxygen 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	-2.8	ALOGPS
logP	-3.3	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	3.78	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	8	ChemAxon
Refractivity	64.08 m³·mol⁻¹	ChemAxon
Polarizability	27 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

HMDB0028801

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

57558415

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44232492

PDB ID

Not Available

ChEBI ID

141429

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Glutaminylleucine (NP0136430)

MOL for NP0136430 (Glutaminylleucine)

3D MOL for NP0136430 (Glutaminylleucine)

3D SDF for NP0136430 (Glutaminylleucine)

3D-SDF for NP0136430 (Glutaminylleucine)

PDB for NP0136430 (Glutaminylleucine)

3D PDB for NP0136430 (Glutaminylleucine)

SMILES for NP0136430 (Glutaminylleucine)

INCHI for NP0136430 (Glutaminylleucine)

Structure for NP0136430 (Glutaminylleucine)

3D Structure for NP0136430 (Glutaminylleucine)