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Showing metabocard for Methylguanidine (HMDB0001522)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:45 UTC
HMDB IDHMDB0001522
Secondary Accession Numbers
  • HMDB01522
Metabolite 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
Data?1676999745
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001522 (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 HMDB0001522 (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 HMDB0001522 (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>
HMDB0001522

> <DATABASE_NAME>
hmdb

> <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 HMDB0001522 (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 HMDB0001522 (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 HMDB0001522 (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 HMDB0001522 (Methylguanidine)

CNC(N)=N
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INCHI for HMDB0001522 (Methylguanidine)

InChI=1S/C2H7N3/c1-5-2(3)4/h1H3,(H4,3,4,5)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1-METHYLGUANIDINEChEBI
MethylguanidinChEBI
MGXChEBI
Monomethyl guanidinChEBI
MonomethylguanidineChEBI
N-MethylguanidineChEBI
N1-MethylguanidineChEBI
Chemical FormulaC2H7N3
Average Molecular Weight73.0971
Monoisotopic Molecular Weight73.063997239
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
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
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological roleIndirect biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.78 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+113.05131661259
DarkChem[M-H]-106.76731661259
AllCCS[M+H]+125.2332859911
AllCCS[M-H]-128.52332859911
DeepCCS[M+H]+118.56730932474
DeepCCS[M-H]-116.67130932474
DeepCCS[M-2H]-151.94630932474
DeepCCS[M+Na]+125.95630932474
AllCCS[M+H]+125.232859911
AllCCS[M+H-H2O]+120.932859911
AllCCS[M+NH4]+129.332859911
AllCCS[M+Na]+130.532859911
AllCCS[M-H]-128.532859911
AllCCS[M+Na-2H]-134.332859911
AllCCS[M+HCOO]-140.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MethylguanidineCNC(N)=N2073.2Standard polar33892256
MethylguanidineCNC(N)=N933.4Standard non polar33892256
MethylguanidineCNC(N)=N1405.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Methylguanidine,1TMS,isomer #1CNC(=N)N[Si](C)(C)C1382.2Semi standard non polar33892256
Methylguanidine,1TMS,isomer #1CNC(=N)N[Si](C)(C)C1034.5Standard non polar33892256
Methylguanidine,1TMS,isomer #1CNC(=N)N[Si](C)(C)C2237.7Standard polar33892256
Methylguanidine,1TMS,isomer #2CN(C(=N)N)[Si](C)(C)C1295.9Semi standard non polar33892256
Methylguanidine,1TMS,isomer #2CN(C(=N)N)[Si](C)(C)C1062.0Standard non polar33892256
Methylguanidine,1TMS,isomer #2CN(C(=N)N)[Si](C)(C)C2039.5Standard polar33892256
Methylguanidine,1TMS,isomer #3CNC(N)=N[Si](C)(C)C1251.5Semi standard non polar33892256
Methylguanidine,1TMS,isomer #3CNC(N)=N[Si](C)(C)C1060.7Standard non polar33892256
Methylguanidine,1TMS,isomer #3CNC(N)=N[Si](C)(C)C1897.3Standard polar33892256
Methylguanidine,2TMS,isomer #1CN(C(=N)N[Si](C)(C)C)[Si](C)(C)C1345.7Semi standard non polar33892256
Methylguanidine,2TMS,isomer #1CN(C(=N)N[Si](C)(C)C)[Si](C)(C)C1189.2Standard non polar33892256
Methylguanidine,2TMS,isomer #1CN(C(=N)N[Si](C)(C)C)[Si](C)(C)C1867.1Standard polar33892256
Methylguanidine,2TMS,isomer #2CNC(=N[Si](C)(C)C)N[Si](C)(C)C1382.4Semi standard non polar33892256
Methylguanidine,2TMS,isomer #2CNC(=N[Si](C)(C)C)N[Si](C)(C)C1155.2Standard non polar33892256
Methylguanidine,2TMS,isomer #2CNC(=N[Si](C)(C)C)N[Si](C)(C)C1947.3Standard polar33892256
Methylguanidine,2TMS,isomer #3CNC(=N)N([Si](C)(C)C)[Si](C)(C)C1386.2Semi standard non polar33892256
Methylguanidine,2TMS,isomer #3CNC(=N)N([Si](C)(C)C)[Si](C)(C)C1181.5Standard non polar33892256
Methylguanidine,2TMS,isomer #3CNC(=N)N([Si](C)(C)C)[Si](C)(C)C1925.1Standard polar33892256
Methylguanidine,2TMS,isomer #4CN(C(N)=N[Si](C)(C)C)[Si](C)(C)C1318.6Semi standard non polar33892256
Methylguanidine,2TMS,isomer #4CN(C(N)=N[Si](C)(C)C)[Si](C)(C)C1203.9Standard non polar33892256
Methylguanidine,2TMS,isomer #4CN(C(N)=N[Si](C)(C)C)[Si](C)(C)C1865.8Standard polar33892256
Methylguanidine,3TMS,isomer #1CN(C(=N[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C1387.2Semi standard non polar33892256
Methylguanidine,3TMS,isomer #1CN(C(=N[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C1215.4Standard non polar33892256
Methylguanidine,3TMS,isomer #1CN(C(=N[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C1702.6Standard polar33892256
Methylguanidine,3TMS,isomer #2CN(C(=N)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1366.6Semi standard non polar33892256
Methylguanidine,3TMS,isomer #2CN(C(=N)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1352.0Standard non polar33892256
Methylguanidine,3TMS,isomer #2CN(C(=N)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1709.5Standard polar33892256
Methylguanidine,3TMS,isomer #3CNC(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1382.5Semi standard non polar33892256
Methylguanidine,3TMS,isomer #3CNC(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1269.1Standard non polar33892256
Methylguanidine,3TMS,isomer #3CNC(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1733.2Standard polar33892256
Methylguanidine,4TMS,isomer #1CN(C(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1462.7Semi standard non polar33892256
Methylguanidine,4TMS,isomer #1CN(C(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1410.3Standard non polar33892256
Methylguanidine,4TMS,isomer #1CN(C(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C1483.2Standard polar33892256
Methylguanidine,1TBDMS,isomer #1CNC(=N)N[Si](C)(C)C(C)(C)C1548.8Semi standard non polar33892256
Methylguanidine,1TBDMS,isomer #1CNC(=N)N[Si](C)(C)C(C)(C)C1184.9Standard non polar33892256
Methylguanidine,1TBDMS,isomer #1CNC(=N)N[Si](C)(C)C(C)(C)C2290.7Standard polar33892256
Methylguanidine,1TBDMS,isomer #2CN(C(=N)N)[Si](C)(C)C(C)(C)C1461.1Semi standard non polar33892256
Methylguanidine,1TBDMS,isomer #2CN(C(=N)N)[Si](C)(C)C(C)(C)C1235.8Standard non polar33892256
Methylguanidine,1TBDMS,isomer #2CN(C(=N)N)[Si](C)(C)C(C)(C)C2212.4Standard polar33892256
Methylguanidine,1TBDMS,isomer #3CNC(N)=N[Si](C)(C)C(C)(C)C1447.4Semi standard non polar33892256
Methylguanidine,1TBDMS,isomer #3CNC(N)=N[Si](C)(C)C(C)(C)C1239.8Standard non polar33892256
Methylguanidine,1TBDMS,isomer #3CNC(N)=N[Si](C)(C)C(C)(C)C2089.4Standard polar33892256
Methylguanidine,2TBDMS,isomer #1CN(C(=N)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1789.9Semi standard non polar33892256
Methylguanidine,2TBDMS,isomer #1CN(C(=N)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1582.0Standard non polar33892256
Methylguanidine,2TBDMS,isomer #1CN(C(=N)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1979.5Standard polar33892256
Methylguanidine,2TBDMS,isomer #2CNC(=N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C1792.0Semi standard non polar33892256
Methylguanidine,2TBDMS,isomer #2CNC(=N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C1463.2Standard non polar33892256
Methylguanidine,2TBDMS,isomer #2CNC(=N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C1977.8Standard polar33892256
Methylguanidine,2TBDMS,isomer #3CNC(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1767.4Semi standard non polar33892256
Methylguanidine,2TBDMS,isomer #3CNC(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1567.9Standard non polar33892256
Methylguanidine,2TBDMS,isomer #3CNC(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1985.6Standard polar33892256
Methylguanidine,2TBDMS,isomer #4CN(C(N)=N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1703.8Semi standard non polar33892256
Methylguanidine,2TBDMS,isomer #4CN(C(N)=N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1554.0Standard non polar33892256
Methylguanidine,2TBDMS,isomer #4CN(C(N)=N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2070.3Standard polar33892256
Methylguanidine,3TBDMS,isomer #1CN(C(=N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1968.7Semi standard non polar33892256
Methylguanidine,3TBDMS,isomer #1CN(C(=N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1830.5Standard non polar33892256
Methylguanidine,3TBDMS,isomer #1CN(C(=N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1950.1Standard polar33892256
Methylguanidine,3TBDMS,isomer #2CN(C(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2002.5Semi standard non polar33892256
Methylguanidine,3TBDMS,isomer #2CN(C(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1990.4Standard non polar33892256
Methylguanidine,3TBDMS,isomer #2CN(C(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1994.1Standard polar33892256
Methylguanidine,3TBDMS,isomer #3CNC(=N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1977.4Semi standard non polar33892256
Methylguanidine,3TBDMS,isomer #3CNC(=N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1850.2Standard non polar33892256
Methylguanidine,3TBDMS,isomer #3CNC(=N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1951.5Standard polar33892256
Methylguanidine,4TBDMS,isomer #1CN(C(=N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2243.3Semi standard non polar33892256
Methylguanidine,4TBDMS,isomer #1CN(C(=N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2204.9Standard non polar33892256
Methylguanidine,4TBDMS,isomer #1CN(C(=N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1923.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Methylguanidine GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9000000000-0b42b86da8534391928a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methylguanidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methylguanidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-007o-9000000000-9397702dbb559840626e2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylguanidine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-05fr-9000000000-534633b3b3a72158d5162012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylguanidine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a4i-9000000000-ee83bc75360621d86cc92012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylguanidine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0006-9000000000-7c1f479fe12182b55b742012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylguanidine , positive-QTOFsplash10-00di-9000000000-44511a31625f714234e52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylguanidine 20V, Positive-QTOFsplash10-0a4i-9000000000-b6d964b0cfb37e04aa3a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylguanidine 40V, Positive-QTOFsplash10-052f-9000000000-18c440680d035ed316d42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylguanidine 10V, Positive-QTOFsplash10-0a4i-9000000000-ecb092d7f7fa515ac8812021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylguanidine 10V, Positive-QTOFsplash10-0a4i-9000000000-cc59ab6824edf551244e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylguanidine 40V, Positive-QTOFsplash10-052f-9000000000-f836ec6360a96bbbd0542021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylguanidine 20V, Positive-QTOFsplash10-0a4i-9000000000-3b8beb22e673f9fe659e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylguanidine 10V, Positive-QTOFsplash10-0a4i-9000000000-7ef3fba0b93f0ffa9dbe2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylguanidine 40V, Positive-QTOFsplash10-0006-9000000000-387fd6ffcb6fd5f260f92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylguanidine 10V, Positive-QTOFsplash10-0ab9-9000000000-d397b15b0bf6997fff622021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylguanidine 40V, Positive-QTOFsplash10-0006-9000000000-772b7e2aeeb01889ea682021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylguanidine 20V, Positive-QTOFsplash10-0a4i-9000000000-b2d8c441679319b6b93b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylguanidine 20V, Positive-QTOFsplash10-0a4i-9000000000-f6850e9d0e6cc606dd732021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylguanidine 10V, Positive-QTOFsplash10-00di-9000000000-c221ed32014cd06b0bfc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylguanidine 20V, Positive-QTOFsplash10-00di-9000000000-83eaeeade889a9c4fad42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylguanidine 40V, Positive-QTOFsplash10-06dl-9000000000-afe740e2160d95afdac82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylguanidine 10V, Negative-QTOFsplash10-00e9-9000000000-471b2da48f84e67fff622017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylguanidine 20V, Negative-QTOFsplash10-00di-9000000000-193b559c768749fc6b0b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylguanidine 40V, Negative-QTOFsplash10-0006-9000000000-3661661b88220d2279072017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylguanidine 10V, Positive-QTOFsplash10-0a4i-9000000000-dd30b822725ba557254e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylguanidine 20V, Positive-QTOFsplash10-0a4i-9000000000-f8ebd4faa807cb8f53212021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylguanidine 40V, Positive-QTOFsplash10-0a4l-9000000000-eba2529a06eb90d77ce52021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Brain
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.10 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified<0.100 uMAdult (>18 years old)Both
Normal		 details
BloodDetected and Quantified0.025 (0.0-0.05) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified < 0.050 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected and Quantified5.25+/- 3.24 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
 details
SalivaDetected and Quantified>10 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.34 +/- 0.14 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0-40 umol/mmol creatinineNewborn (0-30 days old)Both
Normal		 details
UrineDetected and Quantified9.073 +/- 5.348 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.25 +/- 0.72 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
 details
UrineDetected and Quantified0.5 (0.29-0.87) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.7 (1.2-6.0) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified3.3 +/- 1.3 uMAdult (>18 years old)BothChronic renal failure details
BloodDetected and Quantified1.91 +/- 0.82 uMAdult (>18 years old)Bothuremia details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothPancreatic Cancer details
BloodDetected and Quantified10.600 +/- 6.970 uMAdult (>18 years old)Both
Uremia		 details
UrineDetected and Quantified10.32 +/- 7.817 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
Associated Disorders and Diseases
Disease References
Chronic renal failure
  1. Kikuchi T, Orita Y, Ando A, Mikami H, Fujii M, Okada A, Abe H: Liquid-chromatographic determination of guanidino compounds in plasma and erythrocyte of normal persons and uremic patients. Clin Chem. 1981 Nov;27(11):1899-902. [PubMed:7296840 ]
Uremia
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
  2. Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
Pancreatic cancer
  1. Xie G, Lu L, Qiu Y, Ni Q, Zhang W, Gao YT, Risch HA, Yu H, Jia W: Plasma metabolite biomarkers for the detection of pancreatic cancer. J Proteome Res. 2015 Feb 6;14(2):1195-202. doi: 10.1021/pr501135f. Epub 2014 Dec 8. [PubMed:25429707 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00013439
Good Scents IDNot Available
References
Synthesis ReferencePhilippi, E.; Morsch, K. Preparation of methylguanidine according to Werner-Bell. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1927), 60B 2120-2.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [PubMed:12097436 ]
  2. Mizutani N, Hayakawa C, Ohya Y, Watanabe K, Watanabe Y, Mori A: Guanidino compounds in hyperargininemia. Tohoku J Exp Med. 1987 Nov;153(3):197-205. [PubMed:3433275 ]
  3. 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 ]
  4. Lazdins I, Dawborn JK: Concentration of guanidines in normal human plasma. Clin Exp Pharmacol Physiol. 1978 Jan-Feb;5(1):75-80. [PubMed:639360 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. Giovannetti S, Barsotti G: Uremic intoxication. Nephron. 1975;14(2):123-33. [PubMed:1093053 ]
  12. 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 ]
  13. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]