Showing Compound Guanidine (FDB005416)

Record Information

Version

1.0

Creation date

2010-04-08 22:06:40 UTC

Update date

2019-11-26 03:00:33 UTC

Primary ID

FDB005416

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Guanidine

Description

Guanidine 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 Number

50-01-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Aminomethanamidine	ChEBI
Gu	ChEBI
Guanidin	ChEBI
H2N-C(=nh)-NH2	ChEBI
Iminourea	ChEBI
Carbamidine	Kegg
(4-Aminobutyl) guanidine	HMDB
Aminoformamidine	HMDB
Carbamamidine	HMDB
Imidourea	HMDB
Guanidine hydrochloride	HMDB
Guanidine monohydrate	HMDB
Guanidine monohydrochloride	HMDB
Guanidine sulfate	HMDB
Guanidium chloride	HMDB
Chloride, guanidinium	HMDB
Guanidine monohydroiodine	HMDB
Guanidine sulfate (1:1)	HMDB
Guanidine sulfate (2:1)	HMDB
Guanidine sulfite (1:1)	HMDB
Guanidinium	HMDB
Hydrochloride, guanidine	HMDB
Monohydrobromide, guanidine	HMDB
Monohydrochloride, guanidine	HMDB
Phosphate, guanidine	HMDB
Guanidine monohydrobromide	HMDB
Guanidine phosphate	HMDB
Monohydroiodine, guanidine	HMDB
Nitrate, guanidine	HMDB
Chloride, guanidium	HMDB
Guanidine nitrate	HMDB
Guanidinium chloride	HMDB
Monohydrate, guanidine	HMDB
Sulfate, guanidine	HMDB
(NH2)2C=NH	biospider
1184-68-5 (unspecified sulfate)	biospider
1763-07-1 (unspecified phosphate)	biospider
50-01-1 (mono-hydrochloride)	biospider
Bisguanidinium sulfate	biospider
GAI	biospider
GU	biospider
Guanidine, hydrochloride	biospider
Guanidine, sulfate (2:1)	biospider
Guanidinium sulfate	biospider
H2N-C(=NH)-NH2	biospider
NSC7296 (SULFATE, 2:1)	biospider

Predicted Properties

Property	Value	Source
Water Solubility	11.5 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-1.2	ChemAxon
logS	-0.71	ALOGPS
pKa (Strongest Basic)	12.55	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	75.89 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	25.86 m³·mol⁻¹	ChemAxon
Polarizability	5.57 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

Chemical Formula

CH5N3

IUPAC name

guanidine

InChI Identifier

InChI=1S/CH5N3/c2-1(3)4/h(H5,2,3,4)

InChI Key

ZRALSGWEFCBTJO-UHFFFAOYSA-N

Isomeric SMILES

NC(N)=N

Average Molecular Weight

59.0705

Monoisotopic Molecular Weight

59.048347175

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.

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

one-carbon compound (CHEBI:42820 )
guanidines (CHEBI:42820 )
carboxamidine (CHEBI:42820 )
a small molecule (CPD-13517 )

Ontology

Ingestion

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	182.3 oC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	12.5
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Guanidine, 3 TMS, GC-MS Spectrum	splash10-00dj-0920000000-b2c19a9125b059b573fd	Spectrum
GC-MS	Guanidine, non-derivatized, GC-MS Spectrum	splash10-00dj-0920000000-b2c19a9125b059b573fd	Spectrum
Predicted GC-MS	Guanidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-9000000000-6e00e9be1957670e422b	Spectrum
Predicted GC-MS	Guanidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-9000000000-4df2949d18a754b6aa19	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-18b92fabd8878a75412f	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-6675e99565dbe0735311	2012-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9000000000-0bf566c21de369198214	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9000000000-b4670d41c5cfae856086	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9000000000-9431377731da436c5aa7	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9000000000-2280b2044ac4a1f8b7fb	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-8278836749ed05b02fb3	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-154d1302bda42480ad7b	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-ab782a456c989f06bfc8	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-36e3aa30c6cc4afb2049	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-36e3aa30c6cc4afb2049	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-1c8520c5f7efb1187e43	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-1c8520c5f7efb1187e43	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-1c8520c5f7efb1187e43	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

3400

ChEMBL ID

Not Available

KEGG Compound ID

C17349

Pubchem Compound ID

3520

Pubchem Substance ID

Not Available

ChEBI ID

24435

Phenol-Explorer ID

Not Available

DrugBank ID

DB00536

HMDB ID

HMDB01842

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

GUANIDINE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

GAI

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Guanidine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti myasthenic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
convulsant			DUKE
hepatotoxic	50908	A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.	DUKE
hypertensive			DUKE
hypoglycemic	35526	A drug which lowers the blood glucose level.	DUKE
myostimulant			DUKE