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Merck
CN

SMB01381

SAICAriboside

≥95% (HPLC), from synthetic, solid

Synonym(s):

N-Succinyl-5-aminoimidazole-4-carboxamide Ribose

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About This Item

Empirical Formula (Hill Notation):
C13H18N4O9
CAS Number:
17388-80-6
Molecular Weight:
374.30
UNSPSC Code:
12352211
NACRES:
NA.26
MDL number:
MFCD31563062

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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

SMILES string

NC1=C(C(N[C@H](C(O)=O)CC(O)=O)=O)N=CN1[C@H]2[C@H](O)[C@H](O)[C@@H](CO)O2

biological source

synthetic

assay

≥95% (HPLC)

form

solid

color

white to beige

mp

130-135 °C

storage temp.

2-8°C

Quality Level

200

Related Categories

General description

SAICAR (a ribotide) can lose its phosphate group leading to the appearance of a riboside known as succinylaminoimidazolecarboxamide riboside (SAICAriboside or SAICAr) in cerebrospinal fluid, in urine, and, to a lesser extent, in plasma. SAICAriboside is characteristic of ADSL, a heritable deficiency of the enzyme adenylosuccinate lyase (ASL or adenylosuccinase) responsible for metabolizing SAICAR (SZMP) to AICAR (ZMP) and adenylosuccinate (SAMP) to AMP. ASL deficiency causes increased SAICAR & SAMP, and their corresponding rephosphorylated products SAICAr & succinyladenosine (S-Ado).

Preparation Note

Heat sensitive

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000267170
0000267170
0000237992
0000224630
0000237992

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Mass spectrometric analysis of purine de novo biosynthesis intermediates
Madrova, et al.
PLoS ONE, 13, e0208947-e0208947 (2018)
A mild form of adenylosuccinate lyase deficiency in absence of typical brain MRI features diagnosed by whole exome sequencing
Macchiaiolo, et al.
Italian Journal of Pediatrics, 43, 65-65 (2017)
Delphine C Douillet et al.
The Journal of biological chemistry, 294(3), 805-815 (2018-11-28)
5-Aminoimidazole-4-carboxamide 1-β-d-ribofuranoside (AICAR, or acadesine) is a precursor of the monophosphate derivative 5-amino-4-imidazole carboxamide ribonucleoside 5'-phosphate (ZMP), an intermediate in de novo purine biosynthesis. AICAR proved to have promising anti-proliferative properties, although the molecular basis of its toxicity is poorly
Study of purinosome assembly in cell-based model systems with de novo purine synthesis and salvage pathway deficiencies
Baresova, et al.
PLoS ONE, 13, e0201432-e0201432 (2018)
Roxane Marsac et al.
Genetics, 211(4), 1297-1313 (2019-02-01)
Purine homeostasis is ensured through a metabolic network widely conserved from prokaryotes to humans. Purines can either be synthesized de novo, reused, or produced by interconversion of extant metabolites using the so-called recycling pathway. Although thoroughly characterized in microorganisms, such
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