NP-MRD: Showing NP-Card for Arg-Arg-Arg (NP0340130)

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Record Information

Version

2.0

Created at

2024-09-12 01:40:09 UTC

Updated at

2024-09-12 01:40:09 UTC

NP-MRD ID

NP0340130

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Arg-Arg-Arg

Description

Arg-Arg-Arg was first documented in 2022 (PMID: 35964735). Based on a literature review a small amount of articles have been published on Arg-Arg-Arg (PMID: 38633589) (PMID: 35682672).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05272304122D          

 34 33  0  0  0  0            999 V2000
   -7.4783   -0.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7778   -3.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2672   -1.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6681   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2377   -3.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8073   -1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7483    0.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5078   -4.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4571   -1.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3981   -1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5078   -2.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6175   -1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5879   -1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9677   -1.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8285    1.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7778   -6.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8931   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9382   -2.1177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6386    1.3124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2884    1.7801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9677   -6.3272    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3179   -6.7950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332   -0.0908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1632   -1.4940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5584    0.3769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0479   -5.3918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0830   -0.5586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3179   -2.4295    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1575   -2.1177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0479   -1.0263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2377   -1.1822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6976   -0.5586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3474   -0.0908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 19 10  1  0  0  0  0
 20 16  2  0  0  0  0
 21 16  1  0  0  0  0
 22 17  2  0  0  0  0
 23 17  1  0  0  0  0
 24 18  2  0  0  0  0
 25 18  1  0  0  0  0
 26  7  1  0  0  0  0
 26 16  1  0  0  0  0
 27  8  1  0  0  0  0
 27 17  1  0  0  0  0
 28  9  1  0  0  0  0
 28 18  1  0  0  0  0
 29 11  1  4  0  0  0
 29 13  2  0  0  0  0
 30 12  1  4  0  0  0
 30 14  2  0  0  0  0
 31 13  1  0  0  0  0
 32 14  1  0  0  0  0
 33 15  2  0  0  0  0
 34 15  1  0  0  0  0
M  END


  Mrv2104 05272304122D          

 34 33  0  0  0  0            999 V2000
   -7.4783   -0.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7778   -3.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2672   -1.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6681   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2377   -3.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8073   -1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7483    0.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5078   -4.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4571   -1.1822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3981   -1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5078   -2.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6175   -1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5879   -1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9677   -1.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8285    1.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7778   -6.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8931   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9382   -2.1177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6386    1.3124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2884    1.7801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9677   -6.3272    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3179   -6.7950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332   -0.0908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1632   -1.4940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5584    0.3769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0479   -5.3918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0830   -0.5586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3179   -2.4295    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1575   -2.1177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0479   -1.0263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2377   -1.1822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6976   -0.5586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3474   -0.0908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 19 10  1  0  0  0  0
 20 16  2  0  0  0  0
 21 16  1  0  0  0  0
 22 17  2  0  0  0  0
 23 17  1  0  0  0  0
 24 18  2  0  0  0  0
 25 18  1  0  0  0  0
 26  7  1  0  0  0  0
 26 16  1  0  0  0  0
 27  8  1  0  0  0  0
 27 17  1  0  0  0  0
 28  9  1  0  0  0  0
 28 18  1  0  0  0  0
 29 11  1  4  0  0  0
 29 13  2  0  0  0  0
 30 12  1  4  0  0  0
 30 14  2  0  0  0  0
 31 13  1  0  0  0  0
 32 14  1  0  0  0  0
 33 15  2  0  0  0  0
 34 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0340130

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CCCNC(N)=N)C(O)=NC(CCCNC(N)=N)C(O)=NC(CCCNC(N)=N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1/C18H38N12O4/c19-10(4-1-7-26-16(20)21)13(31)29-11(5-2-8-27-17(22)23)14(32)30-12(15(33)34)6-3-9-28-18(24)25/h10-12H,1-9,19H2,(H,29,31)(H,30,32)(H,33,34)(H4,20,21,26)(H4,22,23,27)(H4,24,25,28)

> <INCHI_KEY>
XPSGESXVBSQZPL-UHFFFAOYNA-N

> <FORMULA>
C18H38N12O4

> <MOLECULAR_WEIGHT>
486.582

> <EXACT_MASS>
486.313897752

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
51.64661371231843

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-({2-[(2-amino-5-carbamimidamido-1-hydroxypentylidene)amino]-5-carbamimidamido-1-hydroxypentylidene}amino)-5-carbamimidamidopentanoic acid

> <JCHEM_LOGP>
-7.717364322655934

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
3

> <JCHEM_PKA>
3.748288634287194

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.174460672640647

> <JCHEM_PKA_STRONGEST_BASIC>
12.509343603365684

> <JCHEM_POLAR_SURFACE_AREA>
314.2000000000001

> <JCHEM_REFRACTIVITY>
156.4129000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-({2-[(2-amino-5-carbamimidamido-1-hydroxypentylidene)amino]-5-carbamimidamido-1-hydroxypentylidene}amino)-5-carbamimidamidopentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-23         0                                  
HETATM    1  C   UNK     0     -13.959  -1.043   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.919  -7.445   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.365  -1.916   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -12.447  -1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.910  -6.281   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.374  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -14.463   0.413   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.415  -8.900   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.853  -2.207   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -11.943  -2.789   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.415  -4.826   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.886  -2.789   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.431  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -7.406  -3.662   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.390  -1.334   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -16.480   2.159   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.919 -11.520   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.667  -1.334   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0     -12.951  -3.953   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0     -17.992   2.450   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0     -15.472   3.323   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0      -7.406 -11.811   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0      -9.927 -12.684   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0       2.675  -0.169   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0       2.171  -2.789   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0     -15.976   0.704   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0      -9.423 -10.065   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0       0.155  -1.043   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0      -9.927  -4.535   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0      -5.894  -3.953   0.000  0.00  0.00           N+0
HETATM   31  O   UNK     0      -9.423  -1.916   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -7.910  -2.207   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -6.902  -1.043   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -4.382  -0.169   0.000  0.00  0.00           O+0
CONECT    1    4    7                                                       
CONECT    2    5    8                                                       
CONECT    3    6    9                                                       
CONECT    4    1   10                                                       
CONECT    5    2   11                                                       
CONECT    6    3   12                                                       
CONECT    7    1   26                                                       
CONECT    8    2   27                                                       
CONECT    9    3   28                                                       
CONECT   10    4   13   19                                                  
CONECT   11    5   14   29                                                  
CONECT   12    6   15   30                                                  
CONECT   13   10   29   31                                                  
CONECT   14   11   30   32                                                  
CONECT   15   12   33   34                                                  
CONECT   16   20   21   26                                                  
CONECT   17   22   23   27                                                  
CONECT   18   24   25   28                                                  
CONECT   19   10                                                            
CONECT   20   16                                                            
CONECT   21   16                                                            
CONECT   22   17                                                            
CONECT   23   17                                                            
CONECT   24   18                                                            
CONECT   25   18                                                            
CONECT   26    7   16                                                       
CONECT   27    8   17                                                       
CONECT   28    9   18                                                       
CONECT   29   11   13                                                       
CONECT   30   12   14                                                       
CONECT   31   13                                                            
CONECT   32   14                                                            
CONECT   33   15                                                            
CONECT   34   15                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₃₈N₁₂O₄

Average Mass

486.5820 Da

Monoisotopic Mass

486.31390 Da

IUPAC Name

2-({2-[(2-amino-5-carbamimidamido-1-hydroxypentylidene)amino]-5-carbamimidamido-1-hydroxypentylidene}amino)-5-carbamimidamidopentanoic acid

Traditional Name

2-({2-[(2-amino-5-carbamimidamido-1-hydroxypentylidene)amino]-5-carbamimidamido-1-hydroxypentylidene}amino)-5-carbamimidamidopentanoic acid

CAS Registry Number

Not Available

SMILES

NC(CCCNC(N)=N)C(O)=NC(CCCNC(N)=N)C(O)=NC(CCCNC(N)=N)C(O)=O

InChI Identifier

InChI=1/C18H38N12O4/c19-10(4-1-7-26-16(20)21)13(31)29-11(5-2-8-27-17(22)23)14(32)30-12(15(33)34)6-3-9-28-18(24)25/h10-12H,1-9,19H2,(H,29,31)(H,30,32)(H,33,34)(H4,20,21,26)(H4,22,23,27)(H4,24,25,28)

InChI Key

XPSGESXVBSQZPL-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

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	-7.7	ChemAxon
pKa (Strongest Acidic)	3.17	ChemAxon
pKa (Strongest Basic)	12.51	ChemAxon
Physiological Charge	3	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	314.2 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	156.41 m³·mol⁻¹	ChemAxon
Polarizability	51.65 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ericson MD, Freeman KT, Larson CM, Bouchard JL, John K, Lunzer MM, Koerperich ZM, Haskell-Luevano C: Incorporation of Three Extracyclic Arginine Residues into a Melanocortin Macrocyclic Agonist (c[Pro-His-DPhe-Arg-Trp-Dap-Lys(Arg-Arg-Arg-Ac)-DPro]) Decreases Food Intake When Administered Intrathecally or Subcutaneously Compared to a Macrocyclic Ligand Lacking Extracyclic Arginine Residues (c[Pro-His-DPhe-Arg-Trp-Dap-Ala-DPro)]. ACS Pharmacol Transl Sci. 2024 Apr 2;7(4):1114-1125. doi: 10.1021/acsptsci.4c00011. eCollection 2024 Apr 12. [PubMed:38633589 ]
Lam van TV, Ivanova T, Lindberg I, Bottcher-Friebertshauser E, Steinmetzer T, Hardes K: Design, synthesis, and characterization of novel fluorogenic substrates of the proprotein convertases furin, PC1/3, PC2, PC5/6, and PC7. Anal Biochem. 2022 Oct 15;655:114836. doi: 10.1016/j.ab.2022.114836. Epub 2022 Aug 11. [PubMed:35964735 ]
Rogachevskii IV, Plakhova VB, Penniyaynen VA, Kalinina AD, Podzorova SA, Samosvat DM, Zegrya GG, Krylov BV: Arginine-Containing Tripeptides as Analgesic Substances: The Possible Mechanism of Ligand-Receptor Binding to the Slow Sodium Channel. Int J Mol Sci. 2022 May 26;23(11):5993. doi: 10.3390/ijms23115993. [PubMed:35682672 ]

Showing NP-Card for Arg-Arg-Arg (NP0340130)

MOL for NP0340130 (Arg-Arg-Arg)

3D MOL for NP0340130 (Arg-Arg-Arg)

3D SDF for NP0340130 (Arg-Arg-Arg)

3D-SDF for NP0340130 (Arg-Arg-Arg)

PDB for NP0340130 (Arg-Arg-Arg)

3D PDB for NP0340130 (Arg-Arg-Arg)

SMILES for NP0340130 (Arg-Arg-Arg)

INCHI for NP0340130 (Arg-Arg-Arg)

Structure for NP0340130 (Arg-Arg-Arg)

3D Structure for NP0340130 (Arg-Arg-Arg)