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(2S)-5-[amino(nitramido)methylidene]azaniumyl-2-azaniumylpentanoate

PubChem CID
6991999
Structure
(2S)-5-[amino(nitramido)methylidene]azaniumyl-2-azaniumylpentanoate_small.png
(2S)-5-[amino(nitramido)methylidene]azaniumyl-2-azaniumylpentanoate_3D_Structure.png
Molecular Formula
Synonyms
  • (2S)-5-[amino(nitramido)methylidene]azaniumyl-2-azaniumylpentanoate
  • N omega Nitro L Arginine
Molecular Weight
220.21 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2006-07-28
  • Modify:
    2025-01-04
Description
An inhibitor of nitric oxide synthetase which has been shown to prevent glutamate toxicity. Nitroarginine has been experimentally tested for its ability to prevent ammonia toxicity and ammonia-induced alterations in brain energy and ammonia metabolites. (Neurochem Res 1995:200(4):451-6)

1 Structures

1.1 2D Structure

Chemical Structure Depiction
(2S)-5-[amino(nitramido)methylidene]azaniumyl-2-azaniumylpentanoate.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-5-[amino(nitramido)methylidene]azaniumyl-2-azaniumylpentanoate
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

2.1.2 InChI

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)/p+1/t4-/m0/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.3 InChIKey

MRAUNPAHJZDYCK-BYPYZUCNSA-O
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.4 SMILES

C(C[C@@H](C(=O)[O-])[NH3+])C[NH+]=C(N)N[N+](=O)[O-]
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C6H14N5O4+
Computed by PubChem 2.1 (PubChem release 2019.06.18)

2.3 Synonyms

2.3.1 MeSH Entry Terms

  • N omega Nitro L Arginine
  • N omega-Nitro-L-Arginine
  • N(G)-Nitroarginine
  • N(omega)-Nitroarginine
  • NG Nitro L Arginine
  • NG Nitroarginine
  • NG-Nitro-L-Arginine
  • NG-Nitroarginine
  • Nitroarginine
  • NO2Arg
  • NOARG
  • omega Nitroarginine
  • omega-Nitro-L-Arginine, N
  • omega-Nitroarginine

2.3.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
220.21 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
-3
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
4
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
220.10457894 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
220.10457894 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
166 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
15
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
1
Reference
Computed by PubChem
Property Name
Complexity
Property Value
255
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2010.01.29)

5 Chemical Vendors

6 Pharmacology and Biochemistry

6.1 MeSH Pharmacological Classification

Enzyme Inhibitors
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

7 Literature

7.1 Consolidated References

7.2 NLM Curated PubMed Citations

8 Classification

8.1 MeSH Tree

9 Information Sources

  1. Medical Subject Headings (MeSH)
    LICENSE
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    https://www.nlm.nih.gov/copyright.html
  2. PubChem
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