Guanidinosuccinic acid
PubChem CID: 439918
Connections displayed (default: 10).
Loading graph...
| Compound Synonyms | Guanidinosuccinic acid, 6133-30-8, (S)-2-Guanidinosuccinic acid, N-Amidino-L-aspartic acid, Guanidinosuccinate, L-Aspartic acid,N-(aminoiminomethyl)-, L-N-Amidinoaspartic acid, N-carbamimidoyl-L-aspartic acid, N-Amidino-L-aspartate, N-(Aminoiminomethyl)-L-aspartic acid, (2S)-2-carbamimidamidobutanedioic acid, carbamimidoyl-L-aspartic acid, (2S)-2-(diaminomethylideneamino)butanedioic acid, MFCD00055819, amidino aspartic acid, (S)-2-Guanidinosuccinicacid, SCHEMBL4099868, SCHEMBL25356400, CHEBI:17072, AKOS006272951, AS-63019, HY-113373, CS-0062315, NS00014844, C03139, C16083, Q27102197, (2S)-2-[(DIAMINOMETHYLIDENE)AMINO]BUTANEDIOIC ACID |
|---|---|
| Ghose Rule | False |
| Classyfire Kingdom | Organic compounds |
| Topological Polar Surface Area | 139.0 |
| Hydrogen Bond Donor Count | 4.0 |
| Pfizer 3 75 Rule | True |
| Np Classifier Class | Aminoacids |
| Deep Smiles | OC=O)C[C@@H]C=O)O))N=CN)N |
| Heavy Atom Count | 12.0 |
| Classyfire Class | Carboxylic acids and derivatives |
| Description | Guanidinosuccinic acid (GSA) 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) [HMDB] |
| Classyfire Subclass | Amino acids, peptides, and analogues |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 221.0 |
| Database Name | fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 1.0 |
| Iupac Name | (2S)-2-(diaminomethylideneamino)butanedioic acid |
| Class | Carboxylic acids and derivatives |
| Veber Rule | True |
| Classyfire Superclass | Organic acids and derivatives |
| Xlogp | -2.0 |
| Superclass | Organic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Gsk 4 400 Rule | True |
| Molecular Formula | C5H9N3O4 |
| Inchi Key | VVHOUVWJCQOYGG-REOHCLBHSA-N |
| Silicos It Class | Soluble |
| Rotatable Bond Count | 4.0 |
| State | Solid |
| Synonyms | (2S)-2-Carbamimidamidobutanedioate, (2S)-2-Carbamimidamidobutanedioic acid, Guanidinosuccinate, L-N-Amidinoaspartate, L-N-amidinoaspartic acid, N-(Aminoiminomethyl)-L-aspartate, N-(aminoiminomethyl)-L-aspartic acid, N-Amidino-L-aspartate, N-amidino-L-aspartic acid, N-carbamimidoyl-L-aspartic acid, L-N-Amidinoaspartic acid, N-(Aminoiminomethyl)-L-aspartic acid, N-Amidino-L-aspartic acid, N-Carbamimidoyl-L-aspartic acid, Guanidinosuccinic acid, (DL)-isomer, Guanidinosuccinic acid, guanidinosuccinic acid |
| Substituent Name | Alpha-amino acid or derivatives, N-substituted-alpha-amino acid, Amino fatty acid, Fatty acyl, Fatty acid, Dicarboxylic acid or derivatives, Guanidine, Carboximidamide, Carboxylic acid, Hydrocarbon derivative, Organooxygen compound, Organonitrogen compound, Imine, Carbonyl group, Aliphatic acyclic compound |
| Esol Class | Highly soluble |
| Functional Groups | CC(=O)O, CN=C(N)N |
| Compound Name | Guanidinosuccinic acid |
| Kingdom | Organic compounds |
| Exact Mass | 175.059 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 175.059 |
| Hydrogen Bond Acceptor Count | 5.0 |
| Molecular Weight | 175.14 |
| Gi Absorption | False |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 1.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aliphatic acyclic compounds |
| Lipinski Rule Of 5 | True |
| Inchi | 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 |
| Smiles | C([C@@H](C(=O)O)N=C(N)N)C(=O)O |
| Np Classifier Biosynthetic Pathway | Amino acids and Peptides |
| Defined Bond Stereocenter Count | 0.0 |
| Egan Rule | False |
| Taxonomy Direct Parent | Aspartic acid and derivatives |
| Np Classifier Superclass | Small peptides |
- 1. Outgoing r'ship
FOUND_INto/from Diospyros Melanoxylon (Plant) Rel Props:Reference:ISBN:9788172361150