ContaminantDB: Guanidoacetic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (6)XML

Record Information

Version

1.0

Creation Date

2014-08-29 05:46:47 UTC

Update Date

2016-11-09 01:09:02 UTC

Accession Number

CHEM003109

Identification

Common Name

Guanidoacetic acid

Class

Small Molecule

Description

Guanidinoacetic acid is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. Guanidoacetic acid is a metabolite in the Urea cycle and metabolism of amino groups, and in the metabolic pathways of several amino acids. This includes glycine, serine, threonine, arginine and proline metabolism. Guanidinoacetic acid is also a precursor of creatine, an essential substrate for muscle energy metabolism.

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Affinity Label
Amide
Amine
Food Toxin
Lachrymator
Metabolite
Natural Compound
Organic Compound
Uremic Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Glycocyamine	ChEBI
Guanidinoacetate	ChEBI
N-(Carbamimidoyl)glycine	ChEBI
N-[Amino(imino)methyl]glycine	ChEBI
N-Amidinoglycine	ChEBI
Guanidinoacetic acid	Kegg
Guanidoacetate	Generator
(Carboxymethyl)-guanidine	HMDB
2-[[Amino(imino)methyl]amino]acetate	HMDB
2-[[Amino(imino)methyl]amino]acetic acid	HMDB
a-Guanidinoacetate	HMDB
a-Guanidinoacetic acid	HMDB
alpha-Guanidinoacetate	HMDB
alpha-Guanidinoacetic acid	HMDB
b-Guanidinoacetate	HMDB
b-Guanidinoacetic acid	HMDB
beta-Guanidinoacetate	HMDB
beta-Guanidinoacetic acid	HMDB
Betacyamine	HMDB
Betasyamine	HMDB
Guanidineacetate	HMDB
Guanidineacetic acid	HMDB
Guanidylacetate	HMDB
Guanidylacetic acid	HMDB
Guanyl glycine	HMDB
N-Amidino-glycine	HMDB
[(Aminoiminomethyl)amino]-acetate	HMDB
[(Aminoiminomethyl)amino]-acetic acid	HMDB
Glycocyamine, 2-(14)C-labeled	HMDB
Glycocyamine, ion (1-)	HMDB
Glycocyamine monohydrochloride	HMDB

Chemical Formula

C₃H₇N₃O₂

Average Molecular Mass

117.107 g/mol

Monoisotopic Mass

117.054 g/mol

CAS Registry Number

352-97-6

IUPAC Name

2-carbamimidamidoacetic acid

Traditional Name

glycocyamine

SMILES

NC(=N)NCC(O)=O

InChI Identifier

InChI=1S/C3H7N3O2/c4-3(5)6-1-2(7)8/h1H2,(H,7,8)(H4,4,5,6)

InChI Key

BPMFZUMJYQTVII-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Guanidine
Carboximidamide
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

glycine derivative (CHEBI:16344 )
N-amidino-amino acid (CHEBI:16344 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Brain
Kidney
Liver

Pathways

Name	SMPDB Link	KEGG Link
Arginine and Proline Metabolism	SMP00020	map00330
Glycine and Serine Metabolism	SMP00004	map00260
Argininemia	SMP00357	Not Available
Creatine deficiency, guanidinoacetate methyltransferase deficiency	SMP00504	Not Available
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency)	SMP00188	Not Available
S-Adenosylhomocysteine (SAH) Hydrolase Deficiency	SMP00214	Not Available

Applications

Not Available

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	3.6 mg/mL at 15°C

Predicted Properties

Property	Value	Source
Water Solubility	4.19 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-3.1	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	12.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.2 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	36.72 m³·mol⁻¹	ChemAxon
Polarizability	10.54 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-0901000000-4a89fe463d29379e6339	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-0911000000-542baca9dcca73225bf0	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-006t-0911200000-bb7ea068f193f39c283b	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-0901000000-4a89fe463d29379e6339	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-0911000000-542baca9dcca73225bf0	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-006t-0911200000-bb7ea068f193f39c283b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-c703c631a81e400681bd	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9700000000-1dae820000c4f9ec1662	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-016r-7900000000-4777d20e1ab29262427e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00dl-9000000000-a1b5501bf0f7a9b0489d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9100000000-b61a48cf749b57a2c77e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0gk9-7900000000-5ba298286886c1fabdf5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-00di-9100000000-a5b77a913821d637210f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-00di-9100000000-a5b77a913821d637210f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0gk9-7900000000-5ba298286886c1fabdf5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-014i-6900000000-4d655a894c702bdfdb59	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-23d5c2795ed49f043127	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-ae360cd8919c8fbce3ee	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-93406e2cdb79770abc7d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-c6bd00733ea6fa3f6e5d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-9000000000-2667e0007de6a723415e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0100-9400000000-c5561d5ccaf260c048ec	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0g29-9400000000-421d076c4b6868ca69fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-53db4bf2729a2990a938	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-05fu-9000000000-2cad7322e574eb992175	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-01di-9800000000-967331a78fe4a7917408	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-9000000000-7b281fae734baaa2695d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-4900000000-1b831140a3071dd98e0c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9300000000-b27aea734be08f5d2ddc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dl-9000000000-dea2f28faa5430d7e56f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00xr-9500000000-1ba345c7064e9cb70f9c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-6864d4355d3462fbc69f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-1c36299ab8746bbf67a5	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Endogenous, Ingestion, Dermal (contact)

Mechanism of Toxicity

Uremic toxins such as guanidinoacetic acid are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (2). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (3)

Metabolism

Guanidino acetic acid (GAA) is synthesized in the liver and kidney from Arg and Gly and subsequently methylated by S-adenosylmethionine to form creatine. The conversion of guaniodacetate to creatinine in the liver causes a depletion of methyl groups. This causes homocysteine levels to rise, which has been shown to produce cardiovascular and skeletal problems.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Naturally produced by the body (endogenous). Is used as a supplement to enhance athletic performance.

Minimum Risk Level

Not Available

Health Effects

Acute exposure to guanidoacetic acid can lead to some mild skin and eye irritation. Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. Chronically high levels of guanidoacetic acid are associated with at least 4 inborn errors of metabolism including: Argininemia, Guanidinoacetate methyltransferase deficiency, Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency) and S-Adenosylhomocysteine (SAH) Hydrolase Deficiency.

Symptoms

As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.

Treatment

Chronic Exposure: Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored. Acute Exposure: EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice.

Concentrations

Not Available

External Links

DrugBank ID

DB02751

HMDB ID

HMDB0000128

FooDB ID

FDB005417

Phenol Explorer ID

Not Available

KNApSAcK ID