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Guanidine (FDB005416)

Record Information
Version1.0
Creation date2010-04-08 22:06:40 UTC
Update date2019-11-26 03:00:33 UTC
Primary IDFDB005416
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGuanidine
DescriptionGuanidine apparently acts by enhancing the release of acetylcholine following a nerve impulse. It also appears to slow the rates of depolarization and repolarization of muscle cell membranes.; Guanidine is a crystalline compound of strong alkalinity formed by the oxidation of guanine. It is used in the manufacture of plastics and explosives. It is found in urine as a normal product of protein metabolism. The molecule was first synthesized in 1861 by the oxidative degradation of an aromatic natural product, guanine, isolated from Peruvian guano. Despite the provocative simplicity of the molecule, the crystal structure was first described 148 years later.; Guanidine is a polyamine that can function as a strong organic base existing primarily as guanidium ions at physiological pH. With a pKa of 12.5, guanidine is protonated, with a charge of +1 in physiological conditions. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed). Guanidine is a crystalline compound of strong alkalinity formed by the oxidation of guanine. It is used in the manufacture of plastics and explosives. -- Wikipedia; Guanidines are a group of organic compounds sharing a common functional group with the general structure (R1R2N)(R3R4N)C=N-R5. The central bond within this group is that of an imine; the other recognizable motif within this group is an aminal. Examples of guanidines are arginine, triazabicyclodecene and saxitoxin. other derivatives could include guanidine hydroxide, the active ingredient in some non-lye relaxers. Guanidinium salts are well known for their denaturing action on proteins. Guanidinium chloride is one of the most effective denaturants. In 6 M GndHCl all proteins with an ordered structure lose their structure, and most of them become randomly coiled, that is, they do not contain any residual structure.
CAS Number50-01-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility11.5 g/LALOGPS
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaCH5N3
IUPAC nameguanidine
InChI IdentifierInChI=1S/CH5N3/c2-1(3)4/h(H5,2,3,4)
InChI KeyZRALSGWEFCBTJO-UHFFFAOYSA-N
Isomeric SMILESNC(N)=N
Average Molecular Weight59.0705
Monoisotopic Molecular Weight59.048347175
Classification
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

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point182.3 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKa12.5
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSGuanidine, 3 TMS, GC-MS Spectrumsplash10-00dj-0920000000-b2c19a9125b059b573fdSpectrum
GC-MSGuanidine, non-derivatized, GC-MS Spectrumsplash10-00dj-0920000000-b2c19a9125b059b573fdSpectrum
Predicted GC-MSGuanidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9000000000-6e00e9be1957670e422bSpectrum
Predicted GC-MSGuanidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-9000000000-4df2949d18a754b6aa192012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-18b92fabd8878a75412f2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-6675e99565dbe07353112012-07-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-0bf566c21de3691982142015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9000000000-b4670d41c5cfae8560862015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9000000000-9431377731da436c5aa72015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-2280b2044ac4a1f8b7fb2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-8278836749ed05b02fb32015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-154d1302bda42480ad7b2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-ab782a456c989f06bfc82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-36e3aa30c6cc4afb20492021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-36e3aa30c6cc4afb20492021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-1c8520c5f7efb1187e432021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-1c8520c5f7efb1187e432021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-1c8520c5f7efb1187e432021-09-23View Spectrum
NMRNot Available
ChemSpider ID3400
ChEMBL IDNot Available
KEGG Compound IDC17349
Pubchem Compound ID3520
Pubchem Substance IDNot Available
ChEBI ID24435
Phenol-Explorer IDNot Available
DrugBank IDDB00536
HMDB IDHMDB01842
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDGUANIDINE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDGAI
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGuanidine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti myasthenic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
convulsantDUKE
hepatotoxic50908 A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.DUKE
hypertensiveDUKE
hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
myostimulantDUKE
Enzymes
NameGene NameUniProt ID
Arginine decarboxylaseADCQ96A70
Ribonuclease pancreaticRNASE1P07998
Disks large homolog 4DLG4P78352
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).