NP-MRD: Showing NP-Card for Arginylglutamic acid (NP0136347)

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Record Information

Version

2.0

Created at

2022-05-12 15:12:14 UTC

Updated at

2022-05-12 15:12:14 UTC

NP-MRD ID

NP0136347

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Arginylglutamic acid

Description

Arginylglutamic acid, also known as arg-glu or N-L-arginyl-L-glutamate, 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. Arginylglutamic acid is a very strong basic compound (based on its pKa). Arginylglutamic acid was first documented in 2009 (PMID: 19778072). It is an incomplete breakdown product of protein digestion or protein catabolism.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 41  0  0  0  0  0  0  0  0999 V2000
    3.9945   -1.1141    1.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9035   -1.4097    1.3210 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6059   -0.6098    0.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8547   -1.0805    0.0733 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2259    0.7192    0.3298 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8320    1.0984    0.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0609    0.4682   -0.7179 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6103    0.8502   -0.6696 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9348    0.4027    0.6048 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0214   -1.0572    0.6888 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4580    0.8611    0.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7041    2.0871    0.6447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5136   -0.0555    0.5168 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9417    0.3964    0.5120 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4384    0.0586   -0.8383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7972    0.3827   -1.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9559   -0.1751   -0.5838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8871    0.5213   -0.0642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0878   -1.5486   -0.4777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5583   -0.4005    1.5798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9004   -1.3063    2.1495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8562   -0.1595    1.9672 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8802   -2.0083   -0.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6615   -0.4459    0.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9376    1.4345    0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4885    0.8339    1.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6986    2.2012    0.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1549   -0.6482   -0.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4859    0.7859   -1.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5209    1.9485   -0.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0520    0.3981   -1.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4909    0.7755    1.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846   -1.4318   -0.1800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3769   -1.3291    1.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693   -1.0713    0.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8853    1.4868    0.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1836   -1.0224   -1.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7354    0.5895   -1.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9232    1.5176   -1.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8789    0.0366   -2.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7908   -2.0895   -0.9661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5114   -0.8903    2.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 19  1  0
 17 18  2  0
 14 20  1  0
 20 22  1  0
 20 21  2  0
 10 33  1  0
 10 34  1  0
  9 32  1  1
  8 30  1  0
  8 31  1  0
  7 28  1  0
  7 29  1  0
  6 26  1  0
  6 27  1  0
  5 25  1  0
  4 23  1  0
  4 24  1  0
  2  1  1  0
 13 35  1  0
 14 36  1  1
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 19 41  1  0
 22 42  1  0
M  END


  Mrv1652304062013222D          

 21 20  0  0  0  0            999 V2000
 2502.0114 2501.9570    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2502.0114 2501.1318    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2502.7323 2500.7322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.4470 2501.1440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.7323 2499.9069    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2502.0175 2499.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.3026 2499.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.5898 2499.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.8752 2499.9069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.1604 2499.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.1604 2498.6680    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2498.4150 2499.9235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2503.4470 2499.4933    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2501.2965 2502.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.5818 2501.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.8671 2502.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.1503 2501.9570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.8671 2503.1939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.7261 2502.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.4408 2501.9570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.7261 2503.1939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1 14  1  0  0  0  0
  1 19  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  5 13  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
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136347

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H21N5O5/c12-6(2-1-5-15-11(13)14)9(19)16-7(10(20)21)3-4-8(17)18/h6-7H,1-5,12H2,(H,16,19)(H,17,18)(H,20,21)(H4,13,14,15)/t6-,7-/m0/s1

> <INCHI_KEY>
HFKJBCPRWWGPEY-BQBZGAKWSA-N

> <FORMULA>
C11H21N5O5

> <MOLECULAR_WEIGHT>
303.319

> <EXACT_MASS>
303.154268796

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
30.205849151741752

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]pentanedioic acid

> <ALOGPS_LOGP>
-3.70

> <JCHEM_LOGP>
-6.2865045214381166

> <ALOGPS_LOGS>
-2.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.9982820595694553

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2292217098348655

> <JCHEM_PKA_STRONGEST_BASIC>
12.036268878574822

> <JCHEM_POLAR_SURFACE_AREA>
191.61999999999998

> <JCHEM_REFRACTIVITY>
82.01089999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.91e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
Arg-Glu

> <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    4670.4214670.320   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4670.4214668.779   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4671.7674668.033   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    4673.1014668.802   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    4671.7674666.493   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4670.4334665.721   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4669.0984666.493   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    4667.7684665.721   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0    4666.4344666.493   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0    4665.0994665.721   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0    4665.0994664.180   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0    4663.7084666.524   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0    4673.1014665.721   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0    4669.0874671.088   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4667.7534670.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    4666.4194671.088   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    4665.0814670.320   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0    4666.4194672.629   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0    4671.7554671.088   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0    4673.0894670.320   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0    4671.7554672.629   0.000  0.00  0.00           O+0
CONECT    1    2   14   19                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    5                                                            
CONECT   14    1   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    1   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Value	Source
Arg-glu	ChEBI
H-Arg-glu-OH	ChEBI
N-L-Arginyl-L-glutamic acid	ChEBI
N-L-Arginyl-L-glutamate	Generator
Arginylglutamate	Generator
L-Arginyl-L-glutamate	HMDB
Arginine glutamate dipeptide	HMDB
Arginine glutamic acid dipeptide	HMDB
Arginine-glutamate dipeptide	HMDB
Arginine-glutamic acid dipeptide	HMDB
Arginyl-glutamate	HMDB
Arginyl-glutamic acid	HMDB
L-Arg-L-glu	HMDB
L-Arginyl-L-glutamic acid	HMDB
N-Arginylglutamate	HMDB
N-Arginylglutamic acid	HMDB
NSC 186916	HMDB
R-e Dipeptide	HMDB
RE dipeptide	HMDB

Chemical Formula

C₁₁H₂₁N₅O₅

Average Mass

303.3190 Da

Monoisotopic Mass

303.15427 Da

IUPAC Name

(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]pentanedioic acid

Traditional Name

Arg-Glu

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H21N5O5/c12-6(2-1-5-15-11(13)14)9(19)16-7(10(20)21)3-4-8(17)18/h6-7H,1-5,12H2,(H,16,19)(H,17,18)(H,20,21)(H4,13,14,15)/t6-,7-/m0/s1

InChI Key

HFKJBCPRWWGPEY-BQBZGAKWSA-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
Glutamic acid 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
Dicarboxylic acid or derivatives
Fatty amide
N-acyl-amine
Fatty acid
Fatty acyl
Amino acid
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Carboxylic acid salt
Guanidine
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Carboxylic acid
Hydrocarbon derivative
Organic oxygen compound
Primary aliphatic amine
Organopnictogen compound
Organic nitrogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic salt
Amine
Primary amine
Organic zwitterion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:63357 )

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	-3.7	ALOGPS
logP	-6.3	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.23	ChemAxon
pKa (Strongest Basic)	12.04	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	191.62 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	82.01 m³·mol⁻¹	ChemAxon
Polarizability	30.21 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0028708

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6995003

PDB ID

Not Available

ChEBI ID

63357

Good Scents ID

Not Available

References

General References

Campos SR, Baptista AM: Conformational analysis in a multidimensional energy landscape: study of an arginylglutamate repeat. J Phys Chem B. 2009 Dec 10;113(49):15989-6001. doi: 10.1021/jp902991u. [PubMed:19778072 ]

Showing NP-Card for Arginylglutamic acid (NP0136347)

MOL for NP0136347 (Arginylglutamic acid)

3D MOL for NP0136347 (Arginylglutamic acid)

3D SDF for NP0136347 (Arginylglutamic acid)

3D-SDF for NP0136347 (Arginylglutamic acid)

PDB for NP0136347 (Arginylglutamic acid)

3D PDB for NP0136347 (Arginylglutamic acid)

SMILES for NP0136347 (Arginylglutamic acid)

INCHI for NP0136347 (Arginylglutamic acid)

Structure for NP0136347 (Arginylglutamic acid)

3D Structure for NP0136347 (Arginylglutamic acid)