NP-MRD: Showing NP-Card for Arginylaspartic acid (NP0136344)

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Record Information

Version

2.0

Created at

2022-05-12 15:12:08 UTC

Updated at

2022-05-12 15:12:08 UTC

NP-MRD ID

NP0136344

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Arginylaspartic acid

Description

Arginylaspartic acid, also known as arginylaspartate or RD, 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. Arginylaspartic acid was first documented in 1999 (PMID: 10513634). Arginylaspartic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 38  0  0  0  0  0  0  0  0999 V2000
   -5.5182   -0.5744    0.4956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5040    0.4560    0.6143 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6772    1.2025   -0.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7794    2.5967    0.1971 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7622    0.6638   -1.0111 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4369   -0.7266   -1.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6434   -1.0952    0.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3450   -0.3092    0.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4716   -0.6630   -0.9188 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2512   -2.0990   -0.7683 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8110    0.0625   -0.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9005    1.1954   -1.3406 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8978   -0.4990   -0.1580 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2069    0.1345    0.0037 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3885    0.6184    1.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6745    1.3146    1.6295 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1195    1.5364    2.7930 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4684    1.7689    0.5904 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2665   -0.8587   -0.2898 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0299   -1.8653   -1.0177 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5438   -0.7406    0.2163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6852    3.0652    0.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9615    3.1394    0.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3272    1.2969   -1.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9095   -1.0710   -1.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3926   -1.3316   -0.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4391   -2.1857    0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2184   -0.9040    1.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7813   -0.6262    1.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5237    0.7622    0.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0189   -0.3947   -1.8082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0162   -2.3785    0.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3364   -2.5035   -1.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7986   -1.4609    0.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2970    0.9897   -0.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2932   -0.2561    2.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5502    1.3111    1.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1128    1.8995   -0.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9672   -1.4705    0.8131 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 18  1  0
 16 17  2  0
 14 19  1  0
 19 21  1  0
 19 20  2  0
 10 32  1  0
 10 33  1  0
  9 31  1  6
  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
 13 34  1  0
 14 35  1  6
 15 36  1  0
 15 37  1  0
 18 38  1  0
 21 39  1  0
M  END


  Mrv1652304062013212D          

 20 19  0  0  0  0            999 V2000
 2502.1430 2500.0010    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2501.4290 2499.5877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7129 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.9989 2499.5877    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2499.2849 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.5709 2499.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8569 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.1429 2499.5877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2496.4289 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2496.4289 2500.8255    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2495.7149 2499.5877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.9989 2498.7633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7129 2500.8255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.8570 2499.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.5710 2500.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2504.2850 2499.5877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2503.5710 2500.8255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1430 2500.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.8570 2501.2366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4290 2501.2366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 14  1  0  0  0  0
  1 18  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 13  2  0  0  0  0
  4  5  1  0  0  0  0
  4 12  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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136344

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H19N5O5/c11-5(2-1-3-14-10(12)13)8(18)15-6(9(19)20)4-7(16)17/h5-6H,1-4,11H2,(H,15,18)(H,16,17)(H,19,20)(H4,12,13,14)/t5-,6-/m0/s1

> <INCHI_KEY>
SIFXMYAHXJGAFC-WDSKDSINSA-N

> <FORMULA>
C10H19N5O5

> <MOLECULAR_WEIGHT>
289.292

> <EXACT_MASS>
289.138618732

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
28.164137453601178

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-3.74

> <JCHEM_LOGP>
-6.5291698978751285

> <ALOGPS_LOGS>
-2.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
5.138542468715838

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3035126233235843

> <JCHEM_PKA_STRONGEST_BASIC>
12.035020071569967

> <JCHEM_POLAR_SURFACE_AREA>
191.61999999999995

> <JCHEM_REFRACTIVITY>
77.25589999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]butanedioic 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    4670.6674666.669   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4669.3344665.897   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4667.9974666.669   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4666.6654665.897   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4665.3324666.669   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4663.9994665.897   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4662.6664666.669   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0    4661.3334665.897   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0    4660.0014666.669   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0    4660.0014668.208   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0    4658.6684665.897   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0    4666.6654664.358   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0    4667.9974668.208   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    4672.0004665.897   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4673.3334666.669   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    4674.6654665.897   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    4673.3334668.208   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0    4670.6674668.208   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    4672.0004668.975   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0    4669.3344668.975   0.000  0.00  0.00           O+0
CONECT    1    2   14   18                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    4                                                            
CONECT   13    3                                                            
CONECT   14    1   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
L-Arg-L-asp	ChEBI
RD	ChEBI
Arginylaspartate	Generator
Arg-asp	HMDB
Arginine aspartate dipeptide	HMDB
Arginine aspartic acid dipeptide	HMDB
Arginine-aspartate dipeptide	HMDB
Arginine-aspartic acid dipeptide	HMDB
Arginyl-aspartate	HMDB
Arginyl-aspartic acid	HMDB
L-Arginyl-L-aspartate	HMDB
L-Arginyl-L-aspartic acid	HMDB
N-Arginylaspartate	HMDB
N-Arginylaspartic acid	HMDB
N-L-Arginyl-L-aspartate	HMDB
N-L-Arginyl-L-aspartic acid	HMDB
R-D Dipeptide	HMDB
RD Dipeptide	HMDB
Arginylaspartic acid	ChEBI

Chemical Formula

C₁₀H₁₉N₅O₅

Average Mass

289.2920 Da

Monoisotopic Mass

289.13862 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H19N5O5/c11-5(2-1-3-14-10(12)13)8(18)15-6(9(19)20)4-7(16)17/h5-6H,1-4,11H2,(H,15,18)(H,16,17)(H,19,20)(H4,12,13,14)/t5-,6-/m0/s1

InChI Key

SIFXMYAHXJGAFC-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
Aspartic 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:73812 )

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	-6.5	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	3.3	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	9	ChemAxon
Refractivity	77.26 m³·mol⁻¹	ChemAxon
Polarizability	28.16 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

HMDB0028705

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

7009611

PDB ID

Not Available

ChEBI ID

73812

Good Scents ID

Not Available

References

General References

Takao K, Samejima K: Arginyl-tRNA-protein transferase activities in crude supernatants of rat tissues. Biol Pharm Bull. 1999 Sep;22(9):1007-9. doi: 10.1248/bpb.22.1007. [PubMed:10513634 ]

Showing NP-Card for Arginylaspartic acid (NP0136344)

MOL for NP0136344 (Arginylaspartic acid)

3D MOL for NP0136344 (Arginylaspartic acid)

3D SDF for NP0136344 (Arginylaspartic acid)

3D-SDF for NP0136344 (Arginylaspartic acid)

PDB for NP0136344 (Arginylaspartic acid)

3D PDB for NP0136344 (Arginylaspartic acid)

SMILES for NP0136344 (Arginylaspartic acid)

INCHI for NP0136344 (Arginylaspartic acid)

Structure for NP0136344 (Arginylaspartic acid)

3D Structure for NP0136344 (Arginylaspartic acid)