NP-MRD: Showing NP-Card for Arginylisoleucine (NP0136351)

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Record Information

Version

2.0

Created at

2022-05-12 15:12:20 UTC

Updated at

2022-05-12 15:12:20 UTC

NP-MRD ID

NP0136351

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Arginylisoleucine

Description

Arginylisoleucine, also known as RI or L-arg-L-ile, 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. Arginylisoleucine is a very strong basic compound (based on its pKa). Arginylisoleucine was first documented in 1983 (PMID: 6419713). It is an incomplete breakdown product of protein digestion or protein catabolism.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 44  0  0  0  0  0  0  0  0999 V2000
    3.1060    1.6902    2.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417    1.1197    2.0576 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6093    1.3401    0.7769 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8012    2.4174    0.2745 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3639    0.5260   -0.0747 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0698   -0.1821   -1.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2754   -1.3933   -1.2636 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8637   -1.4610   -0.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3857   -1.1458    0.4495 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0492   -1.9431    1.4487 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0927   -1.3457    0.6010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4539   -2.1393    1.4972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0590   -0.7018   -0.1935 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742   -0.9618    0.0286 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1399   -1.4957   -1.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4707   -1.6785   -2.2084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4793   -1.7894   -1.1519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1960    0.3152    0.4291 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6738    0.8246    1.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0503    1.3312   -0.6684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8114    2.6103   -0.3603 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0990    3.3970    0.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9562    2.2162   -0.2835 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4021    0.4381    0.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6175    0.6147   -1.9689 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0560   -0.3657   -1.8292 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4199   -1.8517   -2.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8742   -2.2072   -0.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4908   -2.4740   -1.2630 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2531   -0.7764   -1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5087   -0.0801    0.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7437   -1.6957    2.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8731   -2.9590    1.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8322   -0.0350   -0.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5887   -1.7281    0.8426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8704   -2.7225   -1.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2713    0.0913    0.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6189    1.1419    1.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2696    1.6940    2.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7585    0.0387    2.5098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9987    1.6315   -0.8261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4484    0.9188   -1.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1881    3.2675    0.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7843    2.3700    0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9297    3.1385   -1.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  1  0
 20 18  1  0
 18 19  1  0
 18 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
 11  9  1  0
  9 10  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
 14 15  1  0
 15 17  1  0
 15 16  2  0
 21 43  1  0
 21 44  1  0
 21 45  1  0
 20 41  1  0
 20 42  1  0
 18 37  1  1
 19 38  1  0
 19 39  1  0
 19 40  1  0
 14 35  1  1
 13 34  1  0
  9 31  1  1
 10 32  1  0
 10 33  1  0
  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
 17 36  1  0
M  END


  Mrv1652304062013232D          

 20 19  0  0  0  0            999 V2000
 2503.2070 2501.1030    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2503.2070 2501.9287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2503.9201 2502.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2504.6350 2501.9287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2503.9201 2503.1683    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2503.2070 2503.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4921 2503.1683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7772 2503.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0622 2503.1683    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3492 2503.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3492 2504.4056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6341 2503.1683    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2504.6350 2503.5799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4921 2500.6913    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2501.7772 2501.1030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0602 2500.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.4921 2499.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2503.9221 2500.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2504.6371 2501.1030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2503.9221 2499.8656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  1 14  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  6  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
 14 17  1  1  0  0  0
 15 16  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136351

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H25N5O3/c1-3-7(2)9(11(19)20)17-10(18)8(13)5-4-6-16-12(14)15/h7-9H,3-6,13H2,1-2H3,(H,17,18)(H,19,20)(H4,14,15,16)/t7-,8-,9-/m0/s1

> <INCHI_KEY>
QYLJIYOGHRGUIH-CIUDSAMLSA-N

> <FORMULA>
C12H25N5O3

> <MOLECULAR_WEIGHT>
287.364

> <EXACT_MASS>
287.195739685

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
31.005912186761595

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-methylpentanoic acid

> <ALOGPS_LOGP>
-3.09

> <JCHEM_LOGP>
-2.3475939465075393

> <ALOGPS_LOGS>
-2.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.780571137706396

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8274211953274886

> <JCHEM_PKA_STRONGEST_BASIC>
12.008684693248492

> <JCHEM_POLAR_SURFACE_AREA>
154.32

> <JCHEM_REFRACTIVITY>
84.81709999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-methylpentanoic 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    4672.6534668.726   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    4672.6534670.267   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    4673.9844671.040   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    4675.3194670.267   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    4673.9844672.581   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4672.6534673.349   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4671.3194672.581   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    4669.9844673.349   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0    4668.6494672.581   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0    4667.3194673.349   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0    4667.3194674.890   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0    4665.9844672.581   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0    4675.3194673.349   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0    4671.3194667.957   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4669.9844668.726   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    4668.6464667.957   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    4671.3194666.416   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    4673.9884667.957   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    4675.3234668.726   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0    4673.9884666.416   0.000  0.00  0.00           O+0
CONECT    1    2   14   18                                                  
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   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14                                                            
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
Arginyl-isoleucine	ChEBI
L-Arg-L-ile	ChEBI
RI	ChEBI
Arg-ile	HMDB
Arginine isoleucine dipeptide	HMDB
Arginine-isoleucine dipeptide	HMDB
L-Arginyl-L-isoleucine	HMDB
N-Arginylisoleucine	HMDB
N-L-Arginyl-L-isoleucine	HMDB
R-I dipeptide	HMDB
RI dipeptide	HMDB
Arginylisoleucine	ChEBI

Chemical Formula

C₁₂H₂₅N₅O₃

Average Mass

287.3640 Da

Monoisotopic Mass

287.19574 Da

IUPAC Name

(2S,3S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-methylpentanoic acid

Traditional Name

(2S,3S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-methylpentanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H25N5O3/c1-3-7(2)9(11(19)20)17-10(18)8(13)5-4-6-16-12(14)15/h7-9H,3-6,13H2,1-2H3,(H,17,18)(H,19,20)(H4,14,15,16)/t7-,8-,9-/m0/s1

InChI Key

QYLJIYOGHRGUIH-CIUDSAMLSA-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
Isoleucine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Alpha-amino acid or derivatives
Branched fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Fatty amide
N-acyl-amine
Guanidine
Amino acid or derivatives
Secondary carboxylic acid amide
Amino acid
Carboxamide group
Carboxylic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Carboximidamide
Primary aliphatic amine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Amine
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:73814 )

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	-3.1	ALOGPS
logP	-2.3	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.83	ChemAxon
pKa (Strongest Basic)	12.01	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	154.32 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	84.82 m³·mol⁻¹	ChemAxon
Polarizability	31.01 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

HMDB0028712

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

7009553

PDB ID

Not Available

ChEBI ID

73814

Good Scents ID

Not Available

References

General References

Kanapka JA, Kleinberg I: Catabolism of arginine by the mixed bacteria in human salivary sediment under conditions of low and high glucose concentration. Arch Oral Biol. 1983;28(11):1007-15. doi: 10.1016/0003-9969(83)90055-9. [PubMed:6419713 ]

Showing NP-Card for Arginylisoleucine (NP0136351)

MOL for NP0136351 (Arginylisoleucine)

3D MOL for NP0136351 (Arginylisoleucine)

3D SDF for NP0136351 (Arginylisoleucine)

3D-SDF for NP0136351 (Arginylisoleucine)

PDB for NP0136351 (Arginylisoleucine)

3D PDB for NP0136351 (Arginylisoleucine)

SMILES for NP0136351 (Arginylisoleucine)

INCHI for NP0136351 (Arginylisoleucine)

Structure for NP0136351 (Arginylisoleucine)

3D Structure for NP0136351 (Arginylisoleucine)