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Showing NP-Card for nitroarginine (NP0200430)

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Record Information
Version2.0
Created at2022-09-04 19:16:47 UTC
Updated at2022-09-04 19:16:47 UTC
NP-MRD IDNP0200430
Secondary Accession NumbersNone
Natural Product Identification
Common Namenitroarginine
DescriptionNitroarginine belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Nitroarginine is a very strong basic compound (based on its pKa). nitroarginine is found in Trypanosoma brucei. An L-arginine derivative that is L-arginine in which the terminal nitrogen of the guanidyl group is replaced by a nitro group.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0200430 (nitroarginine)


  Mrv0541 02231217322D          

 15 14  0  0  1  0            999 V2000
    9.9513    4.0954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.0329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.2355    3.2704    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    4.9500    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  CHG  2  10   1  11  -1
M  END
Download

3D MOL for NP0200430 (nitroarginine)

     RDKit          3D

 28 27  0  0  0  0  0  0  0  0999 V2000
    3.5872    0.4224   -2.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7727   -0.0047   -1.5933 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8653    0.0467   -0.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6395    0.6730   -0.9726 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5029    0.7406   -0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1937   -0.5578    0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3435   -0.3313    1.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3794    0.6461    0.6011 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4409    0.7582    1.6298 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9979    0.1655   -0.6398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3277    0.0884   -1.6945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3203   -0.2082   -0.6666 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1278   -0.5384    0.5692 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2433   -1.3990    0.7603 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.1257   -2.6019    0.9918 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5167   -0.8486    0.6817 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.5405    1.1416   -1.9231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2354    1.4406   -0.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7936    1.1479    0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5790   -1.0514   -0.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4978   -1.3136    0.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9771    0.0578    2.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8438   -1.3083    1.3588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9632    1.6554    0.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3324    1.0440    1.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1766    1.5857    2.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6515   -1.0621   -0.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5493   -0.3885    1.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  3 13  1  0
 13 14  1  0
 14 16  1  0
 14 15  2  0
  8 10  1  0
 10 12  1  0
 10 11  2  0
  9 25  1  0
  9 26  1  0
  8 24  1  6
  7 22  1  0
  7 23  1  0
  6 20  1  0
  6 21  1  0
  5 18  1  0
  5 19  1  0
  4 17  1  0
  2  1  1  0
 13 28  1  0
 12 27  1  0
M  CHG  2  14   1  16  -1
M  END
Download

3D SDF for NP0200430 (nitroarginine)


  Mrv0541 02231217322D          

 15 14  0  0  1  0            999 V2000
    9.9513    4.0954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9513    3.2704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2368    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5224    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8079    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0934    3.2704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789    2.0329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    3.2704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.2355    3.2704    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    4.9500    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3802    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6658    2.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  CHG  2  10   1  11  -1
M  END
> <DATABASE_ID>
NP0200430

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H13N5O4/c7-4(5(12)13)2-1-3-9-6(8)10-11(14)15/h4H,1-3,7H2,(H,12,13)(H3,8,9,10)/t4-/m0/s1

> <INCHI_KEY>
MRAUNPAHJZDYCK-BYPYZUCNSA-N

> <FORMULA>
C6H13N5O4

> <MOLECULAR_WEIGHT>
219.1985

> <EXACT_MASS>
219.096753929

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
20.323635797536582

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-5-(1-nitrocarbamimidamido)pentanoic acid

> <ALOGPS_LOGP>
-2.79

> <JCHEM_LOGP>
-3.3690660966825363

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.087917740510816

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8305252111253836

> <JCHEM_PKA_STRONGEST_BASIC>
9.161510244915318

> <JCHEM_POLAR_SURFACE_AREA>
157.04999999999995

> <JCHEM_REFRACTIVITY>
60.909400000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.74e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nitroarginine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0200430 (nitroarginine)

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PDB for NP0200430 (nitroarginine)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      18.576   7.645   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      18.576   6.105   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.242   5.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.908   6.105   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.575   5.335   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      13.241   6.105   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      11.907   5.335   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      11.907   3.795   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      10.574   6.105   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       9.240   5.335   0.000  0.00  0.00           N+1
HETATM   11  O   UNK     0       7.906   6.105   0.000  0.00  0.00           O-1
HETATM   12  O   UNK     0       9.240   3.795   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      19.909   5.335   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      21.243   6.105   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      19.909   3.795   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    2   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

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3D PDB for NP0200430 (nitroarginine)
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SMILES for NP0200430 (nitroarginine)
N[C@@H](CCCNC(=N)N[N+]([O-])=O)C(O)=O
Download
INCHI for NP0200430 (nitroarginine)
InChI=1S/C6H13N5O4/c7-4(5(12)13)2-1-3-9-6(8)10-11(14)15/h4H,1-3,7H2,(H,12,13)(H3,8,9,10)/t4-/m0/s1
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View in JSmol
Synonyms
ValueSource
Ngamma-nitro-L-arginineChEBI
N(g)-Nitro-L-arginineKegg
N Omega-nitro-L-arginineMeSH
N(g)-NitroarginineMeSH
N(Omega)-nitroarginineMeSH
Omega-nitroarginineMeSH
Omega-nitro-L-arginine, NMeSH
NG NitroarginineMeSH
NG-NitroarginineMeSH
NOARGMeSH
Omega nitroarginineMeSH
N Omega nitro L arginineMeSH
NG nitro L ArginineMeSH
NG-nitro-L-ArginineMeSH
NO2argMeSH
N(Γ)-nitro-L-arginineGenerator
Chemical FormulaC6H13N5O4
Average Mass219.1985 Da
Monoisotopic Mass219.09675 Da
IUPAC Name(2S)-2-amino-5-(1-nitrocarbamimidamido)pentanoic acid
Traditional Namenitroarginine
CAS Registry NumberNot Available
SMILES
N[C@@H](CCCNC(=N)N[N+]([O-])=O)C(O)=O
InChI Identifier
InChI=1S/C6H13N5O4/c7-4(5(12)13)2-1-3-9-6(8)10-11(14)15/h4H,1-3,7H2,(H,12,13)(H3,8,9,10)/t4-/m0/s1
InChI KeyMRAUNPAHJZDYCK-BYPYZUCNSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Trypanosoma bruceiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentL-alpha-amino acids  
Alternative Parents
Substituents
  • L-alpha-amino acid
    • 

  • Nitro fatty acid
    • 

  • Nitroguanidine
    • 

  • Fatty acid
    • 

  • Fatty acyl
    • 

  • Nitramine
    • 

  • Guanidine
    • 

  • Amino acid
    • 

  • Organic nitro compound
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboximidamide
    • 

  • Allyl-type 1,3-dipolar organic compound
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Organic 1,3-dipolar compound
    • 

  • Carbonyl group
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Amine
    • 

  • Organic zwitterion
    • 

  • Organic nitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.8ALOGPS
logP-3.4ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)1.83ChemAxon
pKa (Strongest Basic)9.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area157.05 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity60.91 m³·mol⁻¹ChemAxon
Polarizability20.32 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB04223  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC03417  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNitroarginine  
METLIN IDNot Available
PubChem Compound440005  
PDB IDNot Available
ChEBI ID27960  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]