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Showing NP-Card for NG,NG-Dimethyl-L-arginine (NP0334597)

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Record Information
Version2.0
Created at2024-09-10 19:04:39 UTC
Updated at2024-09-10 19:04:39 UTC
NP-MRD IDNP0334597
Secondary Accession NumbersNone
Natural Product Identification
Common NameNG,NG-Dimethyl-L-arginine
DescriptionAsymmetric dimethylarginine, also known as N(g),N(g)-dimethylarginine or ADMA, belongs to the class of organic compounds known as arginine and derivatives. Arginine and derivatives are compounds containing arginine or a derivative thereof resulting from reaction of arginine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Asymmetric dimethylarginine is a very strong basic compound (based on its pKa). Asymmetric dimethylarginine exists in all eukaryotes, ranging from yeast to humans. Outside of the human body, Asymmetric dimethylarginine is found, on average, in the highest concentration within a few different foods, such as wheats, barley, and oats and in a lower concentration in turnips, saskatoon berries, and spinachs. Asymmetric dimethylarginine has also been detected, but not quantified in, pulses. This could make asymmetric dimethylarginine a potential biomarker for the consumption of these foods. Asymmetric dimethylarginine is a potentially toxic compound. NG,NG-Dimethyl-L-arginine was first documented in 1999 (PMID: 10218738). A L-arginine derivative having two methyl groups both attached to the primary amino moiety of the guanidino group (PMID: 16119611) (PMID: 15568284) (PMID: 15558588).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334597 (NG,NG-Dimethyl-L-arginine)


  Mrv0541 02231215392D          

 14 13  0  0  1  0            999 V2000
    1.0461    3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    3.0789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    3.0789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   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  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  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  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
M  END
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3D MOL for NP0334597 (NG,NG-Dimethyl-L-arginine)

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3D SDF for NP0334597 (NG,NG-Dimethyl-L-arginine)

  Mrv0541 02231215392D          

 14 13  0  0  1  0            999 V2000
    1.0461    3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    3.0789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    3.0789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   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  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  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  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0334597

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CCC\N=C(/N)N(C)C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H18N4O2/c1-12(2)8(10)11-5-3-4-6(9)7(13)14/h6H,3-5,9H2,1-2H3,(H2,10,11)(H,13,14)/t6-/m0/s1

> <INCHI_KEY>
YDGMGEXADBMOMJ-LURJTMIESA-N

> <FORMULA>
C8H18N4O2

> <MOLECULAR_WEIGHT>
202.2541

> <EXACT_MASS>
202.14297584

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
22.186030281533142

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-5-[(E)-[amino(dimethylamino)methylidene]amino]pentanoic acid

> <ALOGPS_LOGP>
-3.13

> <JCHEM_LOGP>
-2.6729980412943983

> <ALOGPS_LOGS>
-1.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.539262506302749

> <JCHEM_PKA_STRONGEST_BASIC>
12.34050755300345

> <JCHEM_POLAR_SURFACE_AREA>
104.94

> <JCHEM_REFRACTIVITY>
53.699600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.77e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
asymmetric dimethylarginine

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0334597 (NG,NG-Dimethyl-L-arginine)
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PDB for NP0334597 (NG,NG-Dimethyl-L-arginine)
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  C   UNK     0       1.953   7.287   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.953   5.747   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       0.619   4.977   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.286   4.977   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       4.620   5.747   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       3.286   3.437   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       8.621   4.977   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

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3D PDB for NP0334597 (NG,NG-Dimethyl-L-arginine)
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SMILES for NP0334597 (NG,NG-Dimethyl-L-arginine)
N[C@@H](CCC\N=C(/N)N(C)C)C(O)=O
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INCHI for NP0334597 (NG,NG-Dimethyl-L-arginine)
InChI=1S/C8H18N4O2/c1-12(2)8(10)11-5-3-4-6(9)7(13)14/h6H,3-5,9H2,1-2H3,(H2,10,11)(H,13,14)/t6-/m0/s1
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View in JSmol
Synonyms
ValueSource
ADMAChEBI
Guanidino-N,N-dimethylarginineChEBI
N,N-DimethylarginineChEBI
N(5)-((Dimethylamino)iminomethyl)-L-ornithineChEBI
NG,NG-Dimethyl-L-arginineChEBI
N(g),N(g)-DimethylarginineChEBI
N(g)-DimethylarginineChEBI
N(g1),N(g1)-DimethylarginineChEBI
Nomega,nomega-dimethyl-L-arginineKegg
2-Amino-5-(amino-dimethylamino-methylidene)amino-pentanoateHMDB
2-Amino-5-(amino-dimethylamino-methylidene)amino-pentanoic acidHMDB
Dimethyl-L-arginineHMDB
N(Omega),N(omega)-dimethyl-L-arginineHMDB
NG,NG-DimethylarginineHMDB
NG-DimethylarginineHMDB
Nomega,nomega'-dimethyl-L-arginineHMDB
Asymmetric dimethylarginineChEBI
Chemical FormulaC8H18N4O2
Average Mass202.2541 Da
Monoisotopic Mass202.14298 Da
IUPAC Name(2S)-2-amino-5-[(E)-[amino(dimethylamino)methylidene]amino]pentanoic acid
Traditional Nameasymmetric dimethylarginine
CAS Registry NumberNot Available
SMILES
N[C@@H](CCC\N=C(/N)N(C)C)C(O)=O
InChI Identifier
InChI=1S/C8H18N4O2/c1-12(2)8(10)11-5-3-4-6(9)7(13)14/h6H,3-5,9H2,1-2H3,(H2,10,11)(H,13,14)/t6-/m0/s1
InChI KeyYDGMGEXADBMOMJ-LURJTMIESA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as arginine and derivatives. Arginine and derivatives are compounds containing arginine or a derivative thereof resulting from reaction of arginine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentArginine and derivatives  
Alternative Parents
Substituents
  • Arginine or derivatives
    • 

  • Alpha-amino acid
    • 

  • L-alpha-amino acid
    • 

  • Fatty acid
    • 

  • Guanidine
    • 

  • Amino acid
    • 

  • Carboximidamide
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Hydrocarbon derivative
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Imine
    • 

  • Carbonyl group
    • 

  • Amine
    • 

  • Organic nitrogen compound
    • 

  • Organic oxide
    • 

  • 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-3.1ALOGPS
logP-2.7ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)2.54ChemAxon
pKa (Strongest Basic)12.34ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.94 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity53.7 m³·mol⁻¹ChemAxon
Polarizability22.19 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001539  
DrugBank IDDB01686  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000508  
KNApSAcK IDNot Available
Chemspider ID110375  
KEGG Compound IDC03626  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAsymmetric dimethylarginine  
METLIN ID6309  
PubChem Compound123831  
PDB IDNot Available
ChEBI ID17929  
Good Scents IDNot Available
References
General References
  1. Surdacki A, Nowicki M, Sandmann J, Tsikas D, Boeger RH, Bode-Boeger SM, Kruszelnicka-Kwiatkowska O, Kokot F, Dubiel JS, Froelich JC: Reduced urinary excretion of nitric oxide metabolites and increased plasma levels of asymmetric dimethylarginine in men with essential hypertension. J Cardiovasc Pharmacol. 1999 Apr;33(4):652-8. [PubMed:10218738  ] 
  2. Watanabe T, Kato S, Sato K, Nagata K: Nitric oxide regulation system in degenerative lumbar disease. Kurume Med J. 2005;52(1-2):39-47. doi: 10.2739/kurumemedj.52.39. [PubMed:16119611  ] 
  3. Nijveldt RJ, Teerlink T, Siroen MP, van der Hoven B, Prins HA, Wiezer MJ, Meijer C, van der Sijp JR, Cuesta MA, Meijer S, van Leeuwen PA: Elevation of asymmetric dimethylarginine (ADMA) in patients developing hepatic failure after major hepatectomy. JPEN J Parenter Enteral Nutr. 2004 Nov-Dec;28(6):382-7. doi:  10.1177/0148607104028006382. [PubMed:15568284  ] 
  4. Siroen MP, Warle MC, Teerlink T, Nijveldt RJ, Kuipers EJ, Metselaar HJ, Tilanus HW, Kuik DJ, van der Sijp JR, Meijer S, van der Hoven B, van Leeuwen PA: The transplanted liver graft is capable of clearing asymmetric dimethylarginine. Liver Transpl. 2004 Dec;10(12):1524-30. doi: 10.1002/lt.20286. [PubMed:15558588  ]