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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:45 UTC

HMDB ID

HMDB0001522

Secondary Accession Numbers

HMDB01522

Metabolite Identification

Common Name

Methylguanidine

Description

Methylguanidine (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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-METHYLGUANIDINE	ChEBI
Methylguanidin	ChEBI
MGX	ChEBI
Monomethyl guanidin	ChEBI
Monomethylguanidine	ChEBI
N-Methylguanidine	ChEBI
N1-Methylguanidine	ChEBI

Chemical Formula

C₂H₇N₃

Average Molecular Weight

73.0971

Monoisotopic Molecular Weight

73.063997239

IUPAC Name

N-methylguanidine

Traditional Name

methylguanidine

CAS Registry Number

471-29-4

SMILES

CNC(N)=N

InChI Identifier

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

InChI Key

CHJJGSNFBQVOTG-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.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Guanidines

Direct Parent

Guanidines

Alternative Parents

Substituents

Guanidine
Carboximidamide
Organopnictogen compound
Hydrocarbon derivative
Imine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

guanidines (CHEBI:16628 )

Ontology

Physiological effect

Health effect

Renal system and urinary system

Renal disorder

Chronic kidney disease (HMDB: HMDB0001522)
Kidney disease (HMDB: HMDB0001522)
Uremia (HMDB: HMDB0001522)
Chronic kidney disease (HMDB: HMDB0001522)

Observation

Nervous system disorder

Coma (HMDB: HMDB0001522)

Central nervous system disorder

Psychiatric disorder

Psychosis (HMDB: HMDB0001522)

Circulatory system disorder

Cardiac disorder

Cardiovascular disease (HMDB: HMDB0001522)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 3433275)
Saliva (PMID: 12097436)
Cerebrospinal Fluid (CSF) (PMID: 3433275)
Cerebrospinal fluid (HMDB: HMDB0001522)

Organ

Brain (HMDB: HMDB0001522)
Liver (HMDB: HMDB0001522)

Excreta

Biofluid or Excreta

Urine (PMID: 7752905)
Feces (PMID: 27543620)

Cellular substructure

Cytoplasm (HMDB: HMDB0001522)
Extracellular (HMDB: HMDB0001522)

Route of exposure

Parenteral

Dermal (HMDB: HMDB0001522)

Enteral

Ingestion (HMDB: HMDB0001522)

Source

Endogenous

Endogenous (HMDB: HMDB0001522)

Plant

Plant (HMDB: HMDB0001522)

Exogenous

Food

Food (HMDB: HMDB0001522)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Fruit

Pome

Apple (FooDB: FOOD00105)

Tropical fruit

Loquat (FooDB: FOOD00076)

Process

Not Available

Role

Biological role

Metabolite (HMDB: HMDB0001522)
Metabolite (HMDB: HMDB0001522)

Modulator

Inhibitor

EC 1.14.13.39 (nitric oxide synthase) inhibitor (HMDB: HMDB0001522)

Indirect biological role

Metabotoxin

Uremic toxin (HMDB: HMDB0001522)
Uremic toxin (HMDB: HMDB0001522)

Industrial application

Pharmaceutical industry

Biomarker

Chronic kidney disease (MarkerDB: MDB00013439)
Uremia (MarkerDB: MDB00013439)
Chronic Renal Failure (MarkerDB: MDB00013439)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.78 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	15.7 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-0.96	ChemAxon
logS	-0.67	ALOGPS
pKa (Strongest Basic)	12.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	61.9 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	30.63 m³·mol⁻¹	ChemAxon
Polarizability	7.57 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	113.051	31661259
DarkChem	[M-H]-	106.767	31661259
AllCCS	[M+H]+	125.23	32859911
AllCCS	[M-H]-	128.523	32859911
DeepCCS	[M+H]+	118.567	30932474
DeepCCS	[M-H]-	116.671	30932474
DeepCCS	[M-2H]-	151.946	30932474
DeepCCS	[M+Na]+	125.956	30932474
AllCCS	[M+H]+	125.2	32859911
AllCCS	[M+H-H2O]+	120.9	32859911
AllCCS	[M+NH4]+	129.3	32859911
AllCCS	[M+Na]+	130.5	32859911
AllCCS	[M-H]-	128.5	32859911
AllCCS	[M+Na-2H]-	134.3	32859911
AllCCS	[M+HCOO]-	140.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methylguanidine	CNC(N)=N	2073.2	Standard polar	33892256
Methylguanidine	CNC(N)=N	933.4	Standard non polar	33892256
Methylguanidine	CNC(N)=N	1405.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methylguanidine,1TMS,isomer #1	CNC(=N)N[Si](C)(C)C	1382.2	Semi standard non polar	33892256
Methylguanidine,1TMS,isomer #1	CNC(=N)N[Si](C)(C)C	1034.5	Standard non polar	33892256
Methylguanidine,1TMS,isomer #1	CNC(=N)N[Si](C)(C)C	2237.7	Standard polar	33892256
Methylguanidine,1TMS,isomer #2	CN(C(=N)N)[Si](C)(C)C	1295.9	Semi standard non polar	33892256
Methylguanidine,1TMS,isomer #2	CN(C(=N)N)[Si](C)(C)C	1062.0	Standard non polar	33892256
Methylguanidine,1TMS,isomer #2	CN(C(=N)N)[Si](C)(C)C	2039.5	Standard polar	33892256
Methylguanidine,1TMS,isomer #3	CNC(N)=N[Si](C)(C)C	1251.5	Semi standard non polar	33892256
Methylguanidine,1TMS,isomer #3	CNC(N)=N[Si](C)(C)C	1060.7	Standard non polar	33892256
Methylguanidine,1TMS,isomer #3	CNC(N)=N[Si](C)(C)C	1897.3	Standard polar	33892256
Methylguanidine,2TMS,isomer #1	CN(C(=N)N[Si](C)(C)C)[Si](C)(C)C	1345.7	Semi standard non polar	33892256
Methylguanidine,2TMS,isomer #1	CN(C(=N)N[Si](C)(C)C)[Si](C)(C)C	1189.2	Standard non polar	33892256
Methylguanidine,2TMS,isomer #1	CN(C(=N)N[Si](C)(C)C)[Si](C)(C)C	1867.1	Standard polar	33892256
Methylguanidine,2TMS,isomer #2	CNC(=N[Si](C)(C)C)N[Si](C)(C)C	1382.4	Semi standard non polar	33892256
Methylguanidine,2TMS,isomer #2	CNC(=N[Si](C)(C)C)N[Si](C)(C)C	1155.2	Standard non polar	33892256
Methylguanidine,2TMS,isomer #2	CNC(=N[Si](C)(C)C)N[Si](C)(C)C	1947.3	Standard polar	33892256
Methylguanidine,2TMS,isomer #3	CNC(=N)N([Si](C)(C)C)[Si](C)(C)C	1386.2	Semi standard non polar	33892256
Methylguanidine,2TMS,isomer #3	CNC(=N)N([Si](C)(C)C)[Si](C)(C)C	1181.5	Standard non polar	33892256
Methylguanidine,2TMS,isomer #3	CNC(=N)N([Si](C)(C)C)[Si](C)(C)C	1925.1	Standard polar	33892256
Methylguanidine,2TMS,isomer #4	CN(C(N)=N[Si](C)(C)C)[Si](C)(C)C	1318.6	Semi standard non polar	33892256
Methylguanidine,2TMS,isomer #4	CN(C(N)=N[Si](C)(C)C)[Si](C)(C)C	1203.9	Standard non polar	33892256
Methylguanidine,2TMS,isomer #4	CN(C(N)=N[Si](C)(C)C)[Si](C)(C)C	1865.8	Standard polar	33892256
Methylguanidine,3TMS,isomer #1	CN(C(=N[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C	1387.2	Semi standard non polar	33892256
Methylguanidine,3TMS,isomer #1	CN(C(=N[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C	1215.4	Standard non polar	33892256
Methylguanidine,3TMS,isomer #1	CN(C(=N[Si](C)(C)C)N[Si](C)(C)C)[Si](C)(C)C	1702.6	Standard polar	33892256
Methylguanidine,3TMS,isomer #2	CN(C(=N)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	1366.6	Semi standard non polar	33892256
Methylguanidine,3TMS,isomer #2	CN(C(=N)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	1352.0	Standard non polar	33892256
Methylguanidine,3TMS,isomer #2	CN(C(=N)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	1709.5	Standard polar	33892256
Methylguanidine,3TMS,isomer #3	CNC(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1382.5	Semi standard non polar	33892256
Methylguanidine,3TMS,isomer #3	CNC(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1269.1	Standard non polar	33892256
Methylguanidine,3TMS,isomer #3	CNC(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1733.2	Standard polar	33892256
Methylguanidine,4TMS,isomer #1	CN(C(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	1462.7	Semi standard non polar	33892256
Methylguanidine,4TMS,isomer #1	CN(C(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	1410.3	Standard non polar	33892256
Methylguanidine,4TMS,isomer #1	CN(C(=N[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	1483.2	Standard polar	33892256
Methylguanidine,1TBDMS,isomer #1	CNC(=N)N[Si](C)(C)C(C)(C)C	1548.8	Semi standard non polar	33892256
Methylguanidine,1TBDMS,isomer #1	CNC(=N)N[Si](C)(C)C(C)(C)C	1184.9	Standard non polar	33892256
Methylguanidine,1TBDMS,isomer #1	CNC(=N)N[Si](C)(C)C(C)(C)C	2290.7	Standard polar	33892256
Methylguanidine,1TBDMS,isomer #2	CN(C(=N)N)[Si](C)(C)C(C)(C)C	1461.1	Semi standard non polar	33892256
Methylguanidine,1TBDMS,isomer #2	CN(C(=N)N)[Si](C)(C)C(C)(C)C	1235.8	Standard non polar	33892256
Methylguanidine,1TBDMS,isomer #2	CN(C(=N)N)[Si](C)(C)C(C)(C)C	2212.4	Standard polar	33892256
Methylguanidine,1TBDMS,isomer #3	CNC(N)=N[Si](C)(C)C(C)(C)C	1447.4	Semi standard non polar	33892256
Methylguanidine,1TBDMS,isomer #3	CNC(N)=N[Si](C)(C)C(C)(C)C	1239.8	Standard non polar	33892256
Methylguanidine,1TBDMS,isomer #3	CNC(N)=N[Si](C)(C)C(C)(C)C	2089.4	Standard polar	33892256
Methylguanidine,2TBDMS,isomer #1	CN(C(=N)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1789.9	Semi standard non polar	33892256
Methylguanidine,2TBDMS,isomer #1	CN(C(=N)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1582.0	Standard non polar	33892256
Methylguanidine,2TBDMS,isomer #1	CN(C(=N)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1979.5	Standard polar	33892256
Methylguanidine,2TBDMS,isomer #2	CNC(=N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	1792.0	Semi standard non polar	33892256
Methylguanidine,2TBDMS,isomer #2	CNC(=N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	1463.2	Standard non polar	33892256
Methylguanidine,2TBDMS,isomer #2	CNC(=N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C	1977.8	Standard polar	33892256
Methylguanidine,2TBDMS,isomer #3	CNC(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1767.4	Semi standard non polar	33892256
Methylguanidine,2TBDMS,isomer #3	CNC(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1567.9	Standard non polar	33892256
Methylguanidine,2TBDMS,isomer #3	CNC(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1985.6	Standard polar	33892256
Methylguanidine,2TBDMS,isomer #4	CN(C(N)=N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1703.8	Semi standard non polar	33892256
Methylguanidine,2TBDMS,isomer #4	CN(C(N)=N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1554.0	Standard non polar	33892256
Methylguanidine,2TBDMS,isomer #4	CN(C(N)=N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2070.3	Standard polar	33892256
Methylguanidine,3TBDMS,isomer #1	CN(C(=N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1968.7	Semi standard non polar	33892256
Methylguanidine,3TBDMS,isomer #1	CN(C(=N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1830.5	Standard non polar	33892256
Methylguanidine,3TBDMS,isomer #1	CN(C(=N[Si](C)(C)C(C)(C)C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1950.1	Standard polar	33892256
Methylguanidine,3TBDMS,isomer #2	CN(C(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2002.5	Semi standard non polar	33892256
Methylguanidine,3TBDMS,isomer #2	CN(C(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1990.4	Standard non polar	33892256
Methylguanidine,3TBDMS,isomer #2	CN(C(=N)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1994.1	Standard polar	33892256
Methylguanidine,3TBDMS,isomer #3	CNC(=N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1977.4	Semi standard non polar	33892256
Methylguanidine,3TBDMS,isomer #3	CNC(=N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1850.2	Standard non polar	33892256
Methylguanidine,3TBDMS,isomer #3	CNC(=N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1951.5	Standard polar	33892256
Methylguanidine,4TBDMS,isomer #1	CN(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)C	2243.3	Semi standard non polar	33892256
Methylguanidine,4TBDMS,isomer #1	CN(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)C	2204.9	Standard non polar	33892256
Methylguanidine,4TBDMS,isomer #1	CN(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)C	1923.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Methylguanidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9000000000-0b42b86da8534391928a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methylguanidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methylguanidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-007o-9000000000-9397702dbb559840626e	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylguanidine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-05fr-9000000000-534633b3b3a72158d516	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylguanidine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0a4i-9000000000-ee83bc75360621d86cc9	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylguanidine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0006-9000000000-7c1f479fe12182b55b74	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylguanidine , positive-QTOF	splash10-00di-9000000000-44511a31625f714234e5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylguanidine 20V, Positive-QTOF	splash10-0a4i-9000000000-b6d964b0cfb37e04aa3a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylguanidine 40V, Positive-QTOF	splash10-052f-9000000000-18c440680d035ed316d4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylguanidine 10V, Positive-QTOF	splash10-0a4i-9000000000-ecb092d7f7fa515ac881	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylguanidine 10V, Positive-QTOF	splash10-0a4i-9000000000-cc59ab6824edf551244e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylguanidine 40V, Positive-QTOF	splash10-052f-9000000000-f836ec6360a96bbbd054	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylguanidine 20V, Positive-QTOF	splash10-0a4i-9000000000-3b8beb22e673f9fe659e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylguanidine 10V, Positive-QTOF	splash10-0a4i-9000000000-7ef3fba0b93f0ffa9dbe	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylguanidine 40V, Positive-QTOF	splash10-0006-9000000000-387fd6ffcb6fd5f260f9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylguanidine 10V, Positive-QTOF	splash10-0ab9-9000000000-d397b15b0bf6997fff62	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylguanidine 40V, Positive-QTOF	splash10-0006-9000000000-772b7e2aeeb01889ea68	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylguanidine 20V, Positive-QTOF	splash10-0a4i-9000000000-b2d8c441679319b6b93b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methylguanidine 20V, Positive-QTOF	splash10-0a4i-9000000000-f6850e9d0e6cc606dd73	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylguanidine 10V, Positive-QTOF	splash10-00di-9000000000-c221ed32014cd06b0bfc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylguanidine 20V, Positive-QTOF	splash10-00di-9000000000-83eaeeade889a9c4fad4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylguanidine 40V, Positive-QTOF	splash10-06dl-9000000000-afe740e2160d95afdac8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylguanidine 10V, Negative-QTOF	splash10-00e9-9000000000-471b2da48f84e67fff62	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylguanidine 20V, Negative-QTOF	splash10-00di-9000000000-193b559c768749fc6b0b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylguanidine 40V, Negative-QTOF	splash10-0006-9000000000-3661661b88220d227907	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylguanidine 10V, Positive-QTOF	splash10-0a4i-9000000000-dd30b822725ba557254e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylguanidine 20V, Positive-QTOF	splash10-0a4i-9000000000-f8ebd4faa807cb8f5321	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylguanidine 40V, Positive-QTOF	splash10-0a4l-9000000000-eba2529a06eb90d77ce5	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 400 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Brain
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	<0.10 uM	Adult (>18 years old)	Both	Normal	22626821	details
Blood	Detected and Quantified	<0.100 uM	Adult (>18 years old)	Both	Normal	12675874	details
Blood	Detected and Quantified	0.025 (0.0-0.05) uM	Adult (>18 years old)	Both	Normal	3433275	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	< 0.050 uM	Adult (>18 years old)	Both	Normal	3433275	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Saliva	Detected and Quantified	5.25+/- 3.24 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected and Quantified	>10 uM	Adult (>18 years old)	Both	Normal	12097436	details
Urine	Detected and Quantified	0.34 +/- 0.14 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	7752905	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22932811	details
Urine	Detected and Quantified	0-40 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	31506554	details
Urine	Detected and Quantified	9.073 +/- 5.348 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21389975	details
Urine	Detected and Quantified	1.25 +/- 0.72 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details
Urine	Detected and Quantified	0.5 (0.29-0.87) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	18818040	details
Urine	Detected and Quantified	2.7 (1.2-6.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	3.3 +/- 1.3 uM	Adult (>18 years old)	Both	Chronic renal failure	7296840	details
Blood	Detected and Quantified	1.91 +/- 0.82 uM	Adult (>18 years old)	Both	uremia	22626821	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Pancreatic Cancer	25429707	details
Blood	Detected and Quantified	10.600 +/- 6.970 uM	Adult (>18 years old)	Both	Uremia	12675874	details
Urine	Detected and Quantified	10.32 +/- 7.817 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Chronic renal failure
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
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 ] 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
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
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

260350 (Pancreatic cancer)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

3768

PubChem Compound

10111

PDB ID

Not Available

ChEBI ID

16628

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00013439

Good Scents ID

Not Available

References

Synthesis Reference

Philippi, 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

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 ]
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 ]
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 ]
Lazdins I, Dawborn JK: Concentration of guanidines in normal human plasma. Clin Exp Pharmacol Physiol. 1978 Jan-Feb;5(1):75-80. [PubMed:639360 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
Giovannetti S, Barsotti G: Uremic intoxication. Nephron. 1975;14(2):123-33. [PubMed:1093053 ]
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 ]
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 ]

Showing metabocard for Methylguanidine (HMDB0001522)

MOL for HMDB0001522 (Methylguanidine)

3D MOL for HMDB0001522 (Methylguanidine)

3D SDF for HMDB0001522 (Methylguanidine)

3D-SDF for HMDB0001522 (Methylguanidine)

PDB for HMDB0001522 (Methylguanidine)

3D PDB for HMDB0001522 (Methylguanidine)

SMILES for HMDB0001522 (Methylguanidine)

INCHI for HMDB0001522 (Methylguanidine)

Structure for HMDB0001522 (Methylguanidine)

3D Structure for HMDB0001522 (Methylguanidine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra