ChemFOnt: Showing chemical card for Guanidinosuccinic acid (CFc000001790)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:30 UTC

Chemfont ID

CFc000001790

Molecule Identification

Common Name

Guanidinosuccinic acid

Definition

Guanidinosuccinic acid (GSA) has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID:22626821 ). It is one of the earliest uremic toxins isolated and its toxicity identified. Its metabolic origins show that it arose from the oxidation of argininosuccinic acid (ASA) by free radicals. The stimulus for this oxidation, occurring optimally in the presence of the failed kidney, is the rising level of urea which, through enzyme inhibition, results in a decline in hepatic levels of the semi-essential amino acid, arginine. It is further noted that concentrations of GSA in both serum and urine decline sharply in animals and humans exposed to the essential amino acid, methionine. Uremic patients suffer from a defective ability to generate methyl groups due to anorexia, dietary restrictions and renal protein leakage. This leads to the accumulation of homocysteine, a substance known to produce vascular damage. Even in healthy subjects intake of choline together with methionine is insufficient to satisfy total metabolic requirements for methyl groups. In end-stage renal disease, therefore, protein restriction contributes to the build-up of toxins in uremia. Replacement using specific amino acid mixtures should be directed toward identified deficiencies and adequacy monitored by following serum levels of the related toxins, in this case GSA and homocysteine. (PMID 12701806 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S)-2-Carbamimidamidobutanedioic acid	ChEBI
L-N-Amidinoaspartic acid	ChEBI
N-(Aminoiminomethyl)-L-aspartic acid	ChEBI
N-Amidino-L-aspartic acid	Kegg
(2S)-2-Carbamimidamidobutanedioate	Generator
L-N-Amidinoaspartate	Generator
N-(Aminoiminomethyl)-L-aspartate	Generator
N-Amidino-L-aspartate	Generator
Guanidinosuccinate	Generator
N-Carbamimidoyl-L-aspartic acid	HMDB
Guanidinosuccinic acid, (DL)-isomer	MeSH, HMDB
Guanidinosuccinic acid	ChEBI

Chemical Formula

C₅H₉N₃O₄

Average Molecular Weight

175.1427

Monoisotopic Molecular Weight

175.059305791

IUPAC Name

(2S)-2-carbamimidamidobutanedioic acid

Traditional Name

N-amidino-L-aspartic acid

CAS Registry Number

6133-30-8

SMILES

NC(=N)N[C@@H](CC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C5H9N3O4/c6-5(7)8-2(4(11)12)1-3(9)10/h2H,1H2,(H,9,10)(H,11,12)(H4,6,7,8)/t2-/m0/s1

InChI Key

VVHOUVWJCQOYGG-REOHCLBHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Aspartic acid and derivatives

Alternative Parents

Substituents

Aspartic acid or derivatives
Dicarboxylic acid or derivatives
Fatty acid
Guanidine
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Carboxylic acid
Organopnictogen compound
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

guanidines (CHEBI:17072 )
C4-dicarboxylic acid (CHEBI:17072 )
L-aspartic acid derivative (CHEBI:17072 )
N-amidino-amino acid (CHEBI:17072 )

Functional Ontology

Physiological effect

Health effect

Renal system and urinary system

Renal disorder

Chronic kidney disease (HMDB: HMDB0003157)
Kidney disease (HMDB: HMDB0003157)
Uremia (HMDB: HMDB0003157)
Chronic kidney disease (HMDB: HMDB0003157)

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Cirrhosis (HMDB: HMDB0003157)

Observation

Nervous system disorder

Coma (HMDB: HMDB0003157)

Central nervous system disorder

Psychiatric disorder

Psychosis (HMDB: HMDB0003157)

Circulatory system disorder

Cardiac disorder

Cardiovascular disease (HMDB: HMDB0003157)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 3433275)
Cerebrospinal Fluid (CSF) (PMID: 3433275)
Cellular Cytoplasm (HMDB: HMDB0003157)
Cerebrospinal fluid (HMDB: HMDB0003157)

Excreta

Biofluid or Excreta

Urine (PMID: 18818040)
Feces (PMID: 27543620)

Cellular substructure

Cytoplasm (HMDB: HMDB0003157)
Membrane (HMDB: HMDB0003157)

Route of exposure

Parenteral

Dermal (HMDB: HMDB0003157)

Enteral

Ingestion (HMDB: HMDB0003157)

Source

Endogenous

Endogenous (HMDB: HMDB0003157)

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)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Chronic kidney disease (MarkerDB: MDB00013446)
Uremia (MarkerDB: MDB00013446)
Cirrhosis (MarkerDB: MDB00013446)
Chronic Renal Failure (MarkerDB: MDB00013446)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.82 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-3.3	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	2.98	ChemAxon
pKa (Strongest Basic)	12.23	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.5 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	47.25 m³·mol⁻¹	ChemAxon
Polarizability	15.13 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