ChemFOnt: Showing chemical card for Succinylaminoimidazole carboxamide riboside (CFc000220558)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:39:44 UTC

Chemfont ID

CFc000220558

Molecule Identification

Common Name

Succinylaminoimidazole carboxamide riboside

Definition

Succinylaminoimidazole carboxamide riboside, also known as SAICAr, is the riboside form of the better known compound SAICAR (the ribotide). Ribosides chemically resemble ribotides except they do not contain a phosphate group. The appearance of succinylaminoimidazolecarboxamide riboside (SAICAriboside) and succinyladenosine (S-Ado) in cerebrospinal fluid, in urine, and, to a lesser extent, in plasma is characteristic of a heritable deficiency known as adenylosuccinate lyase deficiency (ADSL). Adenylosuccinate lyase deficiency is responsible for a range of symptoms that involve psychomotor retardation, often accompanied by epileptic seizures, and autistic features. In adenylosuccinate lyase deficiency it is believed that the buildup of SAICAr causes neurotoxic effects. In the severely affected individuals, the concentration levels of SAICAr and S-Ado are comparable, whereas in people with milder forms of the disease, the concentration of S-Ado is more than double that of those more severely affected, while SAICAr concentration levels remain comparable. Therefore, when present in sufficiently high levels, SAICAr can act as a metabotoxin and an acidogen. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated adenylosuccinate lyase deficiency. Many affected children with organic acidemias experience intellectual disability or delayed development.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
SAICAr	HMDB
SAICAriboside	HMDB
SAICA riboside	HMDB
(2S)-2-[5-Amino-1-(beta-D-ribosyl)imidazole-4-carboxamido]succinic acid	HMDB
(S)-2-[5-Amino-1-(D-ribosyl)imidazole-4-carboxamido]succinate	HMDB
1-(Ribosyl)-4-(N-succinocarboxamide)-5-aminoimidazole	HMDB
1-(Ribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole	HMDB
Ribosyl-4-(N-succinocarboxamide)-5-aminoimidazole	HMDB
Succinyl-5-aminoimidazole-4-carboxamide-1-ribose	HMDB
Succinylaminoimidazolecarboxamide ribose	HMDB
(2S)-2-[5-Amino-1-(b-D-ribosyl)imidazole-4-carboxamido]succinate	HMDB
(2S)-2-[5-Amino-1-(b-D-ribosyl)imidazole-4-carboxamido]succinic acid	HMDB
(2S)-2-[5-Amino-1-(beta-D-ribosyl)imidazole-4-carboxamido]succinate	HMDB
(2S)-2-[5-Amino-1-(β-D-ribosyl)imidazole-4-carboxamido]succinate	HMDB
(2S)-2-[5-Amino-1-(β-D-ribosyl)imidazole-4-carboxamido]succinic acid	HMDB
(S)-2-[5-Amino-1-(D-ribosyl)imidazole-4-carboxamido]succinic acid	HMDB
Succinylaminoimidazole carboxamide riboside	HMDB

Chemical Formula

C₁₃H₁₈N₄O₉

Average Molecular Weight

374.306

Monoisotopic Molecular Weight

374.107378176

IUPAC Name

(2S)-2-({5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-imidazol-4-yl}formamido)butanedioic acid

Traditional Name

(2S)-2-({5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazol-4-yl}formamido)butanedioic acid

CAS Registry Number

17388-80-6

SMILES

NC1=C(N=CN1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O)C(=O)N[C@@H](CC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C13H18N4O9/c14-10-7(11(23)16-4(13(24)25)1-6(19)20)15-3-17(10)12-9(22)8(21)5(2-18)26-12/h3-5,8-9,12,18,21-22H,1-2,14H2,(H,16,23)(H,19,20)(H,24,25)/t4-,5+,8+,9+,12+/m0/s1

InChI Key

XNKLTOHYNRQCLJ-ZZZDFHIKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Imidazole ribonucleosides and ribonucleotides

Sub Class

1-ribosyl-imidazolecarboxamides

Direct Parent

1-ribosyl-imidazolecarboxamides

Alternative Parents

Substituents

1-ribosyl-imidazolecarboxamide
Aspartic acid or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
N-glycosyl compound
Glycosyl compound
Pentose monosaccharide
Alpha-amino acid or derivatives
2-heteroaryl carboxamide
Imidazolyl carboxylic acid derivative
Imidazole-4-carbonyl group
N-substituted imidazole
Monosaccharide
Aminoimidazole
Dicarboxylic acid or derivatives
Imidazole
Vinylogous amide
Tetrahydrofuran
Azole
Heteroaromatic compound
Amino acid or derivatives
Amino acid
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid
Organonitrogen compound
Hydrocarbon derivative
Amine
Organic oxygen compound
Alcohol
Carbonyl group
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Primary amine
Primary alcohol
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Urine (PMID: 10102915)

Source

Exogenous

Exogenous (HMDB: HMDB0240295)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	9.5 g/L	ALOGPS
logP	-2	ALOGPS
logP	-4.2	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	2.99	ChemAxon
pKa (Strongest Basic)	4.55	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	217.46 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	79.78 m³·mol⁻¹	ChemAxon
Polarizability	34.04 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0240295

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

57562912

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54478644

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Succinylaminoimidazole carboxamide riboside (CFc000220558)

MOL for CFc000220558 (Succinylaminoimidazole carboxamide riboside)

3D MOL for CFc000220558 (Succinylaminoimidazole carboxamide riboside)

3D SDF for CFc000220558 (Succinylaminoimidazole carboxamide riboside)

3D-SDF for CFc000220558 (Succinylaminoimidazole carboxamide riboside)

PDB for CFc000220558 (Succinylaminoimidazole carboxamide riboside)

3D PDB for CFc000220558 (Succinylaminoimidazole carboxamide riboside)

SMILES for CFc000220558 (Succinylaminoimidazole carboxamide riboside)

INCHI for CFc000220558 (Succinylaminoimidazole carboxamide riboside)

Structure for CFc000220558 (Succinylaminoimidazole carboxamide riboside)

3D Structure for CFc000220558 (Succinylaminoimidazole carboxamide riboside)