NP-MRD: Showing NP-Card for Asparaginylarginine (NP0136364)

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Record Information

Version

2.0

Created at

2022-05-12 15:12:39 UTC

Updated at

2022-05-12 15:12:39 UTC

NP-MRD ID

NP0136364

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Asparaginylarginine

Description

Asparaginylarginine, also known as N-R dipeptide or asn-arg, 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. Asparaginylarginine 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

 40 39  0  0  0  0  0  0  0  0999 V2000
    3.1858   -0.4603    2.7371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9448    0.1807    2.4417 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1821    0.5273    1.2410 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2418    1.4071    0.9456 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3776    0.0291    0.1774 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1188   -1.3629    0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2148   -1.9258   -0.8732 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7963   -1.5432   -0.8925 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4244   -0.1125   -1.1248 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0682   -0.0187   -1.0766 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6328    0.9008   -0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9215    1.6193    0.5988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1066    1.0324   -0.0700 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7140    0.1355   -1.0039 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4959    0.7393    1.3622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9320    0.8347    1.6009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4487    0.5942    2.8830 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7042    1.1303    0.6648 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7451    0.2003   -2.5396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1608    0.4735   -3.3367 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0763    0.1742   -2.9275 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3465    2.2652    1.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9191    1.2497    0.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0570    0.7165   -0.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8716   -1.7454    1.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1360   -1.8567   -0.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2807   -3.0622   -0.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7251   -1.7822   -1.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2507   -1.9206    0.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2773   -2.1312   -1.7231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8280    0.5933   -0.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6261   -0.6128   -1.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4381    2.0698   -0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4530   -0.8588   -0.8383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3788    0.3881   -1.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1244   -0.2884    1.5859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8992    1.4472    1.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7742   -0.3495    3.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5041    1.3611    3.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3829   -0.0384   -3.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 13 11  1  0
 11 12  2  0
 11 10  1  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 19  1  0
 19 21  1  0
 19 20  2  0
 14 34  1  0
 14 35  1  0
 13 33  1  6
 15 36  1  0
 15 37  1  0
 17 38  1  0
 17 39  1  0
 10 32  1  0
  9 31  1  1
  8 29  1  0
  8 30  1  0
  7 27  1  0
  7 28  1  0
  6 25  1  0
  6 26  1  0
  5 24  1  0
  4 22  1  0
  4 23  1  0
  2  1  1  0
 21 40  1  0
M  END


  Mrv1652304062013252D          

 20 19  0  0  0  0            999 V2000
 2502.8639 2502.0518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2502.8639 2501.2263    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2503.5870 2500.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2504.3019 2501.2385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2503.5870 2500.0013    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2502.8722 2499.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1573 2500.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4424 2499.5876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1573 2500.8268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2504.3019 2499.5876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1490 2502.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4341 2502.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7193 2502.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0044 2502.0518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2896 2502.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2896 2503.2890    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2498.5747 2502.0518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2503.5788 2502.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2504.2936 2502.0518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2503.5788 2503.2890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1 11  1  0  0  0  0
  1 18  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 10  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136364

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H20N6O4/c11-5(4-7(12)17)8(18)16-6(9(19)20)2-1-3-15-10(13)14/h5-6H,1-4,11H2,(H2,12,17)(H,16,18)(H,19,20)(H4,13,14,15)/t5-,6-/m0/s1

> <INCHI_KEY>
NPDLYUOYAGBHFB-WDSKDSINSA-N

> <FORMULA>
C10H20N6O4

> <MOLECULAR_WEIGHT>
288.308

> <EXACT_MASS>
288.154603148

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.561636287050995

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2S)-2-amino-3-carbamoylpropanamido]-5-carbamimidamidopentanoic acid

> <ALOGPS_LOGP>
-3.85

> <JCHEM_LOGP>
-5.123519190470142

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.548091409647217

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4836782763647385

> <JCHEM_PKA_STRONGEST_BASIC>
12.087748224957314

> <JCHEM_POLAR_SURFACE_AREA>
197.41

> <JCHEM_REFRACTIVITY>
79.07809999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.04e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-amino-3-carbamoylpropanamido]-5-carbamimidamidopentanoic 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    4672.0134670.497   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4672.0134668.956   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4673.3624668.210   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    4674.6974668.979   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    4673.3624666.669   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4672.0284665.897   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4670.6944666.669   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0    4669.3594665.897   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0    4670.6944668.210   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0    4674.6974665.897   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0    4670.6784671.265   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    4669.3444670.497   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4668.0094671.265   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0    4666.6754670.497   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0    4665.3414671.265   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0    4665.3414672.806   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0    4664.0064670.497   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0    4673.3474671.265   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    4674.6814670.497   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0    4673.3474672.806   0.000  0.00  0.00           O+0
CONECT    1    2   11   18                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5                                                            
CONECT   11    1   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    1   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

View in JSmol

Synonyms

Value	Source
(2S)-2-{[(2S)-2-amino-1-hydroxy-3-(C-hydroxycarbonimidoyl)propylidene]amino}-5-carbamimidamidopentanoate	HMDB
Asn-arg	HMDB
Asparagine arginine dipeptide	HMDB
Asparagine-arginine dipeptide	HMDB
Asparaginyl-arginine	HMDB
L-Asn-L-arg	HMDB
L-Asparaginyl-L-arginine	HMDB
N-R Dipeptide	HMDB
N2-Asparaginylarginine	HMDB
N2-L-Asparaginyl-L-arginine	HMDB
NR Dipeptide	HMDB

Chemical Formula

C₁₀H₂₀N₆O₄

Average Mass

288.3080 Da

Monoisotopic Mass

288.15460 Da

IUPAC Name

(2S)-2-[(2S)-2-amino-3-carbamoylpropanamido]-5-carbamimidamidopentanoic acid

Traditional Name

(2S)-2-[(2S)-2-amino-3-carbamoylpropanamido]-5-carbamimidamidopentanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H20N6O4/c11-5(4-7(12)17)8(18)16-6(9(19)20)2-1-3-15-10(13)14/h5-6H,1-4,11H2,(H2,12,17)(H,16,18)(H,19,20)(H4,13,14,15)/t5-,6-/m0/s1

InChI Key

NPDLYUOYAGBHFB-WDSKDSINSA-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
Asparagine 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
Fatty amide
N-acyl-amine
Fatty acid
Fatty acyl
Secondary carboxylic acid amide
Primary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Guanidine
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Organic 1,3-dipolar compound
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Primary aliphatic amine
Organic nitrogen compound
Organic oxide
Organonitrogen compound
Carbonyl group
Organooxygen compound
Primary amine
Organic oxygen compound
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	-3.8	ALOGPS
logP	-5.1	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.48	ChemAxon
pKa (Strongest Basic)	12.09	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	197.41 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	79.08 m³·mol⁻¹	ChemAxon
Polarizability	28.56 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

HMDB0028725

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

14299174

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Asparaginylarginine (NP0136364)

MOL for NP0136364 (Asparaginylarginine)

3D MOL for NP0136364 (Asparaginylarginine)

3D SDF for NP0136364 (Asparaginylarginine)

3D-SDF for NP0136364 (Asparaginylarginine)

PDB for NP0136364 (Asparaginylarginine)

3D PDB for NP0136364 (Asparaginylarginine)

SMILES for NP0136364 (Asparaginylarginine)

INCHI for NP0136364 (Asparaginylarginine)

Structure for NP0136364 (Asparaginylarginine)

3D Structure for NP0136364 (Asparaginylarginine)