NP-MRD: Showing NP-Card for Arginylhistidine (NP0136350)

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Record Information

Version

2.0

Created at

2022-05-12 15:12:19 UTC

Updated at

2022-05-12 15:12:19 UTC

NP-MRD ID

NP0136350

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Arginylhistidine

Description

Arginylhistidine, also known as R-H dipeptide or arg-his, 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. Arginylhistidine 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

 43 43  0  0  0  0  0  0  0  0999 V2000
   -5.0676   -0.8189    3.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6468   -0.8886    2.3199 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6051   -0.1778    1.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5381   -0.4736    0.2316 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6574    0.8809    1.1286 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0507    1.3120   -0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1176    0.2416   -0.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0600   -0.1423    0.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0312   -1.1110   -0.1179 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1407   -1.4755    0.9772 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1268   -0.2845   -1.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7358   -0.0545   -2.1445 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1081    0.0638   -0.7287 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4050    0.4306   -0.3398 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4218   -0.6158   -0.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7832   -0.2186   -0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3877   -0.4016    0.9761 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6097    0.1057    0.9351 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8126    0.6198   -0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6831    0.4097   -0.9986 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7745    1.7998   -0.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8962    2.3950   -1.5025 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9731    2.3975   -0.6145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2836   -0.6636   -0.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5650   -0.5213    0.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3882    1.3834    2.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8141    1.5522   -0.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5086    2.2627    0.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7230    0.6088   -1.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7489   -0.6823   -0.8222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5620   -0.5668    1.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708    0.8066    0.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3657   -1.9403   -0.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6964   -1.5334    1.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3266   -2.3722    0.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3623    0.6091   -1.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4195    0.6470    0.8086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3607   -0.9498   -1.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1157   -1.5430   -0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9524   -0.8751    1.8291 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7522    1.1083   -0.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6230    0.7227   -2.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2368    2.7987    0.2931 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  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 14 21  1  0
 21 23  1  0
 21 22  2  0
 20 16  1  0
 10 34  1  0
 10 35  1  0
  9 33  1  6
  8 31  1  0
  8 32  1  0
  7 29  1  0
  7 30  1  0
  6 27  1  0
  6 28  1  0
  5 26  1  0
  4 24  1  0
  4 25  1  0
  2  1  1  0
 13 36  1  0
 14 37  1  1
 15 38  1  0
 15 39  1  0
 17 40  1  0
 19 41  1  0
 20 42  1  0
 23 43  1  0
M  END


  Mrv1652304062013232D          

 22 22  0  0  0  0            999 V2000
 2500.3657 2501.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0806 2501.0263    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2501.0806 2500.2008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2501.8017 2499.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.5166 2500.2129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.8017 2498.9757    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2501.0868 2498.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3716 2498.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6567 2498.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9439 2498.9757    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2290 2498.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.2290 2497.7363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2497.4833 2498.9922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2502.5166 2498.5619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7955 2501.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.5104 2501.0263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7955 2502.2636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9788 2501.5204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2498.3114 2501.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.5663 2500.2508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2499.3913 2500.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6462 2501.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  2 15  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  4  1  1  0  0  0
  6  7  1  0  0  0  0
  6 14  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  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 21 22  2  0  0  0  0
 18 19  1  0  0  0  0
 18 22  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
  1 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136350

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC1=CN=CN1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H21N7O3/c13-8(2-1-3-17-12(14)15)10(20)19-9(11(21)22)4-7-5-16-6-18-7/h5-6,8-9H,1-4,13H2,(H,16,18)(H,19,20)(H,21,22)(H4,14,15,17)/t8-,9-/m0/s1

> <INCHI_KEY>
BNODVYXZAAXSHW-IUCAKERBSA-N

> <FORMULA>
C12H21N7O3

> <MOLECULAR_WEIGHT>
311.346

> <EXACT_MASS>
311.170587564

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
31.80353780866627

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-(1H-imidazol-5-yl)propanoic acid

> <ALOGPS_LOGP>
-3.51

> <JCHEM_LOGP>
-4.450928346385138

> <ALOGPS_LOGS>
-3.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
12.829153042304842

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3618663133718463

> <JCHEM_PKA_STRONGEST_BASIC>
11.975841348373061

> <JCHEM_POLAR_SURFACE_AREA>
183.0

> <JCHEM_REFRACTIVITY>
88.78219999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-(3H-imidazol-4-yl)propanoic 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    4667.3494669.351   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4668.6844668.582   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    4668.6844667.041   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    4670.0304666.296   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    4671.3644667.064   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    4670.0304664.755   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4668.6954663.982   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    4667.3604664.755   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    4666.0264663.982   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0    4664.6954664.755   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0    4663.3614663.982   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0    4663.3614662.441   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0    4661.9694664.785   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0    4671.3644663.982   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0    4670.0184669.351   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    4671.3534668.582   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0    4670.0184670.892   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0    4664.7604669.505   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0    4663.5154668.599   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0    4663.9904667.135   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0    4665.5304667.135   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    4666.0064668.599   0.000  0.00  0.00           C+0
CONECT    1    2   22                                                       
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    6                                                            
CONECT   15    2   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   19   22                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   22   20                                                       
CONECT   22   21   18    1                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Value	Source
(2S)-2-{[(2S)-2-amino-5-carbamimidamido-1-hydroxypentylidene]amino}-3-(1H-imidazol-5-yl)propanoate	HMDB
Arg-his	HMDB
Arginine histidine dipeptide	HMDB
Arginine-histidine dipeptide	HMDB
Arginyl-histidine	HMDB
L-Arg-L-his	HMDB
L-Arginyl-L-histidine	HMDB
N-Arginylhistidine	HMDB
N-L-Arginyl-L-histidine	HMDB
R-H Dipeptide	HMDB
RH Dipeptide	HMDB

Chemical Formula

C₁₂H₂₁N₇O₃

Average Mass

311.3460 Da

Monoisotopic Mass

311.17059 Da

IUPAC Name

(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-(1H-imidazol-5-yl)propanoic acid

Traditional Name

(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-(3H-imidazol-4-yl)propanoic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC1=CN=CN1)C(O)=O

InChI Identifier

InChI=1S/C12H21N7O3/c13-8(2-1-3-17-12(14)15)10(20)19-9(11(21)22)4-7-5-16-6-18-7/h5-6,8-9H,1-4,13H2,(H,16,18)(H,19,20)(H,21,22)(H4,14,15,17)/t8-,9-/m0/s1

InChI Key

BNODVYXZAAXSHW-IUCAKERBSA-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
Histidine or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Imidazolyl carboxylic acid derivative
Fatty amide
N-acyl-amine
Fatty acyl
Azole
Imidazole
Heteroaromatic compound
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Guanidine
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Monocarboxylic acid or derivatives
Carboxylic acid
Primary amine
Organic oxygen compound
Organic oxide
Organopnictogen compound
Primary aliphatic amine
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Amine
Organonitrogen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	-3.5	ALOGPS
logP	-4.5	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.36	ChemAxon
pKa (Strongest Basic)	11.98	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	183 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	88.78 m³·mol⁻¹	ChemAxon
Polarizability	31.8 Å³	ChemAxon
Number of Rings	1	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

HMDB0028711

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

69256407

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Arginylhistidine (NP0136350)

MOL for NP0136350 (Arginylhistidine)

3D MOL for NP0136350 (Arginylhistidine)

3D SDF for NP0136350 (Arginylhistidine)

3D-SDF for NP0136350 (Arginylhistidine)

PDB for NP0136350 (Arginylhistidine)

3D PDB for NP0136350 (Arginylhistidine)

SMILES for NP0136350 (Arginylhistidine)

INCHI for NP0136350 (Arginylhistidine)

Structure for NP0136350 (Arginylhistidine)

3D Structure for NP0136350 (Arginylhistidine)