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Showing NP-Card for Methylguanidine (NP0001278)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-06-29 00:47:06 UTC
NP-MRD IDNP0001278
Secondary Accession NumbersNone
Natural Product Identification
Common NameMethylguanidine
DescriptionMethylguanidine (MG) is a guanidine in which one of the amino hydrogens of guanidine itself is substituted by a methyl group. Methylguanidine is a guanidine compound deriving from protein catabolism. It is also a product of putrefaction. Methylguanidine has a role as a metabolite, an EC 1.14.13.39 (Nitric oxide synthase) inhibitor and as a uremic toxin. It has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ). It accumulates in renal failure, however it also exhibits anti-inflammatory effects. Methylguanidine is synthesized from creatinine concomitant with the synthesis of hydrogen peroxide from endogenous substrates in peroxisomes. Recent evidence suggests that methylguanidine significantly inhibits iNOS activity and TNF- release. This means that methylguandine can attenuate the degree of inflammation and tissue damage associated with endotoxic shock.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001278 (Methylguanidine)


  Mrv1652305271900212D          

  5  4  0  0  0  0            999 V2000
   -0.2843    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4284    0.4132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0005    0.4132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2843   -0.8262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1408    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
M  END
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3D MOL for NP0001278 (Methylguanidine)

HMDB0001522
     RDKit          3D
Methylguanidine
 12 11  0  0  0  0  0  0  0  0999 V2000
    1.6336   -0.3813   -0.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3965   -0.1639    0.5524 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7764    0.3655   -0.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8602    1.5306   -0.5558 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9629   -0.4128   -0.0084 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7002    0.1164   -1.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4527    0.0448    0.5082 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8683   -1.4772   -0.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3790   -0.4277    1.5756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0701    2.1729   -0.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2666   -0.8828   -0.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4943   -0.4845    0.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  3  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  4 10  1  0
  5 11  1  0
  5 12  1  0
M  END
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3D SDF for NP0001278 (Methylguanidine)


  Mrv1652305271900212D          

  5  4  0  0  0  0            999 V2000
   -0.2843    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4284    0.4132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0005    0.4132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2843   -0.8262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1408    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001278

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNC(N)=N

> <INCHI_IDENTIFIER>
InChI=1S/C2H7N3/c1-5-2(3)4/h1H3,(H4,3,4,5)

> <INCHI_KEY>
CHJJGSNFBQVOTG-UHFFFAOYSA-N

> <FORMULA>
C2H7N3

> <MOLECULAR_WEIGHT>
73.0971

> <EXACT_MASS>
73.063997239

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
7.567812806222556

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-methylguanidine

> <ALOGPS_LOGP>
-1.33

> <JCHEM_LOGP>
-0.9592296159999999

> <ALOGPS_LOGS>
-0.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
12.776746351525006

> <JCHEM_POLAR_SURFACE_AREA>
61.9

> <JCHEM_REFRACTIVITY>
30.6334

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methylguanidine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0001278 (Methylguanidine)

HMDB0001522
     RDKit          3D
Methylguanidine
 12 11  0  0  0  0  0  0  0  0999 V2000
    1.6336   -0.3813   -0.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3965   -0.1639    0.5524 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7764    0.3655   -0.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8602    1.5306   -0.5558 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9629   -0.4128   -0.0084 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7002    0.1164   -1.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4527    0.0448    0.5082 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8683   -1.4772   -0.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3790   -0.4277    1.5756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0701    2.1729   -0.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2666   -0.8828   -0.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4943   -0.4845    0.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  3  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  4 10  1  0
  5 11  1  0
  5 12  1  0
M  END
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PDB for NP0001278 (Methylguanidine)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -0.531   0.000   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.800   0.771   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      -1.868   0.771   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      -0.531  -1.542   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       2.129   0.000   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    2                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for NP0001278 (Methylguanidine)

COMPND    HMDB0001522
HETATM    1  C1  UNL     1       1.634  -0.381  -0.144  1.00  0.00           C  
HETATM    2  N1  UNL     1       0.397  -0.164   0.552  1.00  0.00           N  
HETATM    3  C2  UNL     1      -0.776   0.366  -0.016  1.00  0.00           C  
HETATM    4  N2  UNL     1      -0.860   1.531  -0.556  1.00  0.00           N  
HETATM    5  N3  UNL     1      -1.963  -0.413  -0.008  1.00  0.00           N  
HETATM    6  H1  UNL     1       1.700   0.116  -1.116  1.00  0.00           H  
HETATM    7  H2  UNL     1       2.453   0.045   0.508  1.00  0.00           H  
HETATM    8  H3  UNL     1       1.868  -1.477  -0.189  1.00  0.00           H  
HETATM    9  H4  UNL     1       0.379  -0.428   1.576  1.00  0.00           H  
HETATM   10  H5  UNL     1      -0.070   2.173  -0.616  1.00  0.00           H  
HETATM   11  H6  UNL     1      -2.267  -0.883  -0.861  1.00  0.00           H  
HETATM   12  H7  UNL     1      -2.494  -0.484   0.869  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    9
CONECT    3    4    4    5
CONECT    4   10
CONECT    5   11   12
END
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SMILES for NP0001278 (Methylguanidine)

CNC(N)=N
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INCHI for NP0001278 (Methylguanidine)

InChI=1S/C2H7N3/c1-5-2(3)4/h1H3,(H4,3,4,5)
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Synonyms
ValueSource
1-METHYLGUANIDINEChEBI
MethylguanidinChEBI
MGXChEBI
Monomethyl guanidinChEBI
MonomethylguanidineChEBI
N-MethylguanidineChEBI
N1-MethylguanidineChEBI
Chemical FormulaC2H7N3
Average Mass73.0971 Da
Monoisotopic Mass73.06400 Da
IUPAC NameN-methylguanidine
Traditional Namemethylguanidine
CAS Registry Number471-29-4
SMILES
CNC(N)=N
InChI Identifier
InChI=1S/C2H7N3/c1-5-2(3)4/h1H3,(H4,3,4,5)
InChI KeyCHJJGSNFBQVOTG-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Eriobotrya japonicaFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Malus pumilaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as guanidines. Guanidines are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassGuanidines
Direct ParentGuanidines
Alternative Parents
Substituents
  • Guanidine
  • Carboximidamide
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Imine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.78 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility15.7 g/LALOGPS
logP-1.3ALOGPS
logP-0.96ChemAxon
logS-0.67ALOGPS
pKa (Strongest Basic)12.78ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area61.9 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.63 m³·mol⁻¹ChemAxon
Polarizability7.57 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001522
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005421
KNApSAcK IDC00052348
Chemspider ID9707
KEGG Compound IDC02294
BioCyc IDCPD-593
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3768
PubChem Compound10111
PDB IDNot Available
ChEBI ID16628
Good Scents IDNot Available
References
General References
  1. De Deyn PP, Marescau B, D'Hooge R, Possemiers I, Nagler J, Mahler C: Guanidino compound levels in brain regions of non-dialyzed uremic patients. Neurochem Int. 1995 Sep;27(3):227-37. [PubMed:8520461 ]
  2. Lazdins I, Dawborn JK: Concentration of guanidines in normal human plasma. Clin Exp Pharmacol Physiol. 1978 Jan-Feb;5(1):75-80. [PubMed:639360 ]
  3. De Deyn PP, Marescau B, Cuykens JJ, Van Gorp L, Lowenthal A, De Potter WP: Guanidino compounds in serum and cerebrospinal fluid of non-dialyzed patients with renal insufficiency. Clin Chim Acta. 1987 Jul 30;167(1):81-8. [PubMed:3665089 ]
  4. Orita Y, Ando A, Tsubakihara Y, Mikami H, Kikuchi T, Nakata K, Abe H: Tissue and blood cell concentration of methylguanidine in rats and patients with chronic renal failure. Nephron. 1981;27(1):35-9. [PubMed:7219635 ]
  5. Hiraga Y, Kinoshita T: High-performance liquid chromatographic analysis of guanidino compounds using ninhydrin reagent. II. Guanidino compounds in blood of patients on haemodialysis therapy. J Chromatogr. 1985 Aug 9;342(2):269-75. [PubMed:4055949 ]
  6. Boppana VK, Rhodes GR, Brooks DP: Determination of methylguanidine in plasma and urine by high-performance liquid chromatography with fluorescence detection following postcolumn derivatization. Anal Biochem. 1990 Feb 1;184(2):213-8. [PubMed:2327567 ]
  7. Nohara Y, Hanai T, Suzuki J, Matsumoto G, Iinuma F, Kubo H, Kinoshita T, Watanabe M: Automatic system for the assay of guanidino compounds to assess uremic status. Biol Pharm Bull. 2000 Sep;23(9):1015-20. [PubMed:10993196 ]
  8. Fujitsuka N, Yokozawa T, Oura H, Akao T, Kobashi K, Ienaga K, Nakamura K: L-gulono-gamma-lactone oxidase is the enzyme responsible for the production of methylguanidine in the rat liver. Nephron. 1993;63(4):445-51. [PubMed:8459881 ]
  9. Giovannetti S, Barsotti G: Uremic intoxication. Nephron. 1975;14(2):123-33. [PubMed:1093053 ]
  10. Shainkin R, Berkenstadt Y, Giat Y, Berlyne GM: An automated technique for the analysis of plasma guanidino acids, and some findings in chronic renal disease. Clin Chim Acta. 1975 Apr 2;60(1):45-50. [PubMed:236102 ]