NP-MRD: Showing NP-Card for Histidylarginine (NP0136488)

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Record Information

Version

1.0

Created at

2022-05-12 15:15:49 UTC

Updated at

2022-05-12 15:15:49 UTC

NP-MRD ID

NP0136488

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Histidylarginine

Description

H-His-Arg-OH belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. H-His-Arg-OH is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 43  0  0  0  0  0  0  0  0999 V2000
    6.4446    0.0031   -0.9279 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0978    0.8093   -0.3916 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0507    0.6937    0.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5856    1.8158    1.0841 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3653   -0.5398    0.4400 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9304   -1.2174   -0.7901 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8564   -0.4399   -1.4480 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6363   -0.1436   -0.7135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7763   -1.2856   -0.2927 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3995   -0.6814    0.4126 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6774   -0.8750   -0.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8316   -1.5487   -1.1574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8570   -0.2934    0.5614 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4662    0.4367    1.7322 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5747    0.6082   -0.4065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7997    1.1969    0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0705    0.6344    0.1300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8821    1.4862    0.7834 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1473    2.5362    1.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8726    2.3535    0.8557 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3998   -2.2413    0.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5799   -1.9156    1.8523 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8237   -3.5168    0.2901 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1448    2.1283    1.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7172    2.3251    0.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1357   -1.0239    1.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8326   -1.1580   -1.5063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7318   -2.2566   -0.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2838    0.5451   -1.8306 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6182   -0.9799   -2.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8740    0.5277    0.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9587    0.5386   -1.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4087   -1.8197   -1.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2128   -0.1498    1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5398   -1.1276    0.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8433    1.2182    1.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329   -0.1815    2.4448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8915    1.3931   -0.8142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8757   -0.0115   -1.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3448   -0.3163   -0.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4943    3.4078    1.7935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0682    3.0046    1.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6300   -3.9389   -0.6051 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  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  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 21  1  0
 21 23  1  0
 21 22  2  0
 20 16  1  0
 14 36  1  0
 14 37  1  0
 13 35  1  1
 15 38  1  0
 15 39  1  0
 17 40  1  0
 19 41  1  0
 20 42  1  0
 10 34  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
 23 43  1  0
M  END


  Mrv1652304062013472D          

 22 22  0  0  0  0            999 V2000
10019.449710022.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10020.166310021.6006    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10020.880810022.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10021.595210021.6006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10022.310110022.0131    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10023.024210021.6006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.738210022.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10024.452310021.6006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10025.168410022.0131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10025.882410021.6006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10025.882410020.7757    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10026.596510022.0131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10022.310110022.8386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10023.024210023.2515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10021.595210023.2515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10020.880810022.8386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10020.166310020.7757    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10018.065110022.0964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10017.396210021.6104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10017.651710020.8240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10018.478510020.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10018.733910021.6104    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  0  0  0  0
  2 17  1  1  0  0  0
  3  4  1  0  0  0  0
  3 16  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 13  1  6  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
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 21 22  2  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 18 19  1  0  0  0  0
 18 22  1  0  0  0  0
  1 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136488

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H21N7O3/c13-8(4-7-5-16-6-18-7)10(20)19-9(11(21)22)2-1-3-17-12(14)15/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>
NIKBMHGRNAPJFW-IUCAKERBSA-N

> <FORMULA>
C12H21N7O3

> <MOLECULAR_WEIGHT>
311.346

> <EXACT_MASS>
311.170587564

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
31.77489856789113

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-3.52

> <JCHEM_LOGP>
-4.449345877345903

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.872860489072249

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4012755091681144

> <JCHEM_PKA_STRONGEST_BASIC>
12.026312422448019

> <JCHEM_POLAR_SURFACE_AREA>
183.0

> <JCHEM_REFRACTIVITY>
88.78219999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S)-2-amino-3-(3H-imidazol-4-yl)propanamido]-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    8702.9738707.758   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8704.3108706.988   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8705.6448707.758   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0    8706.9788706.988   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0    8708.3128707.758   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8709.6458706.988   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8710.9788707.758   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8712.3118706.988   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0    8713.6488707.758   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0    8714.9808706.988   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0    8714.9808705.448   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0    8716.3138707.758   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0    8708.3128709.299   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    8709.6458710.069   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8706.9788710.069   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8705.6448709.299   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0    8704.3108705.448   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0    8700.3888707.913   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0    8699.1408707.006   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0    8699.6178705.538   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0    8701.1608705.538   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8701.6378707.006   0.000  0.00  0.00           C+0
CONECT    1    2   22                                                       
CONECT    2    1    3   17                                                  
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    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   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    3                                                            
CONECT   17    2                                                            
CONECT   18   19   22                                                       
CONECT   19   20   18                                                       
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
H-R dipeptide	HMDB
HR dipeptide	HMDB
His-Arg	HMDB
Histidine arginine dipeptide	HMDB
Histidine-arginine dipeptide	HMDB
Histidinyl-arginine	HMDB
Histidinylarginine	HMDB
Histidyl-arginine	HMDB
Histidylarginine	HMDB
L-His-L-Arg	HMDB
L-Histidinyl-L-arginine	HMDB
L-Histidyl-L-arginine	HMDB
N2-Histidinylarginine	HMDB
N2-Histidylarginine	HMDB
N2-L-Histidinyl-L-arginine	HMDB
N2-L-Histidyl-L-arginine	HMDB

Chemical Formula

C₁₂H₂₁N₇O₃

Average Mass

311.3460 Da

Monoisotopic Mass

311.17059 Da

IUPAC Name

(2S)-2-[(2S)-2-amino-3-(1H-imidazol-5-yl)propanamido]-5-carbamimidamidopentanoic acid

Traditional Name

(2S)-2-[(2S)-2-amino-3-(3H-imidazol-4-yl)propanamido]-5-carbamimidamidopentanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H21N7O3/c13-8(4-7-5-16-6-18-7)10(20)19-9(11(21)22)2-1-3-17-12(14)15/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

NIKBMHGRNAPJFW-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 peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
Histidine 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
Imidazolyl carboxylic acid derivative
Aralkylamine
Fatty amide
Fatty acyl
Heteroaromatic compound
Azole
Imidazole
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Guanidine
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Organic oxygen compound
Organic oxide
Organic nitrogen compound
Primary aliphatic amine
Hydrocarbon derivative
Carbonyl group
Organonitrogen compound
Organooxygen compound
Amine
Primary amine
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	-4.4	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.4	ChemAxon
pKa (Strongest Basic)	12.03	ChemAxon
Physiological Charge	1	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	31.77 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

HMDB0028879

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5731232

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7408563

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Histidylarginine (NP0136488)

MOL for NP0136488 (Histidylarginine)

3D MOL for NP0136488 (Histidylarginine)

3D SDF for NP0136488 (Histidylarginine)

3D-SDF for NP0136488 (Histidylarginine)

PDB for NP0136488 (Histidylarginine)

3D PDB for NP0136488 (Histidylarginine)

SMILES for NP0136488 (Histidylarginine)

INCHI for NP0136488 (Histidylarginine)

Structure for NP0136488 (Histidylarginine)

3D Structure for NP0136488 (Histidylarginine)