Record Information
Version1.0
Creation Date2016-09-30 22:48:03 UTC
Update Date2020-05-11 20:55:46 UTC
BMDB IDBMDB0001842
Secondary Accession Numbers
  • BMDB01842
Metabolite Identification
Common NameGuanidine
DescriptionGuanidine, also known as Gu or H2N-C(=nh)-NH2, 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. Guanidine is a drug which is used for the reduction of the symptoms of muscle weakness and easy fatigability associated with the myasthenic syndrome of eaton-lambert. it is not indicated for treating myasthenia gravis. Guanidine is a very strong basic compound (based on its pKa). In cattle, guanidine is involved in the metabolic pathway called the purine metabolism pathway. Guanidine is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
AminomethanamidineChEBI
GuChEBI
GuanidinChEBI
H2N-C(=nh)-NH2ChEBI
IminoureaChEBI
CarbamidineKegg
(4-Aminobutyl) guanidineHMDB
AminoformamidineHMDB
CarbamamidineHMDB
ImidoureaHMDB
Guanidine hydrochlorideHMDB
Guanidine monohydrateHMDB
Guanidine monohydrochlorideHMDB
Guanidine sulfateHMDB
Guanidium chlorideHMDB
Chloride, guanidiniumHMDB
Guanidine monohydroiodineHMDB
Guanidine sulfate (1:1)HMDB
Guanidine sulfate (2:1)HMDB
Guanidine sulfite (1:1)HMDB
GuanidiniumHMDB
Hydrochloride, guanidineHMDB
Monohydrobromide, guanidineHMDB
Monohydrochloride, guanidineHMDB
Phosphate, guanidineHMDB
Guanidine monohydrobromideHMDB
Guanidine phosphateHMDB
Monohydroiodine, guanidineHMDB
Nitrate, guanidineHMDB
Chloride, guanidiumHMDB
Guanidine nitrateHMDB
Guanidinium chlorideHMDB
Monohydrate, guanidineHMDB
Sulfate, guanidineHMDB
Chemical FormulaCH5N3
Average Molecular Weight59.0705
Monoisotopic Molecular Weight59.048347175
IUPAC Nameguanidine
Traditional Nameguanidine
CAS Registry Number50-01-1
SMILES
NC(N)=N
InChI Identifier
InChI=1S/CH5N3/c2-1(3)4/h(H5,2,3,4)
InChI KeyZRALSGWEFCBTJO-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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point182.3 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility829 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.9ALOGPS
logP-1.2ChemAxon
logS-0.71ALOGPS
pKa (Strongest Basic)12.55ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area75.89 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity25.86 m³·mol⁻¹ChemAxon
Polarizability5.57 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00dj-0920000000-b2c19a9125b059b573fdView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00dj-0920000000-b2c19a9125b059b573fdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9000000000-6e00e9be1957670e422bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-9000000000-4df2949d18a754b6aa19View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-18b92fabd8878a75412fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-6675e99565dbe0735311View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-0bf566c21de369198214View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9000000000-b4670d41c5cfae856086View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9000000000-9431377731da436c5aa7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-2280b2044ac4a1f8b7fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-8278836749ed05b02fb3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-154d1302bda42480ad7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-ab782a456c989f06bfc8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-36e3aa30c6cc4afb2049View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-36e3aa30c6cc4afb2049View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-1c8520c5f7efb1187e43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-1c8520c5f7efb1187e43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-1c8520c5f7efb1187e43View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Adrenal Cortex
  • Adrenal Gland
  • Adrenal Medulla
  • Brain
  • Cartilage
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Skeletal Muscle
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adrenal CortexExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Adrenal GlandExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Adrenal MedullaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
CartilageExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PancreasExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001842
DrugBank IDDB00536
Phenol Explorer Compound IDNot Available
FooDB IDFDB005416
KNApSAcK IDNot Available
Chemspider ID3400
KEGG Compound IDC17349
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGuanidine
METLIN ID6342
PubChem Compound3520
PDB IDNot Available
ChEBI ID42820
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in nucleic acid binding
Specific function:
Endonuclease that catalyzes the cleavage of RNA on the 3' side of pyrimidine nucleotides. Acts on single-stranded and double-stranded RNA.
Gene Name:
RNASE1
Uniprot ID:
P61823
Molecular weight:
16461.0
General function:
Carbohydrate transport and metabolism
Specific function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin-dependent kinase II and LCK tyrosine kinase (By similarity).
Gene Name:
SLC22A1
Uniprot ID:
A7MBE0
Molecular weight:
62502.0