AICA-Riboside, 5′-Phosphate - ≥95%, high purity , CAS No.3031-94-5

  • ≥95%
Item Number
A346730
Grouped product items
SKUSizeAvailabilityPrice Qty
A346730-1mg
1mg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$45.90
A346730-5mg
5mg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$180.90
A346730-10mg
10mg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$359.90
A346730-25mg
25mg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$808.90
A346730-50mg
50mg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$1,455.90

an AMP-activated protein kinase (AMPK) activator mimic

Basic Description

SynonymsNSC 283955 | NSC 292227 | ZMP | 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide | 5-amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide | F0X88YW0YK | Z-nucleotide | 5-Aminoimidazole-4-carboxamide-1-?-D-Ribofuranosyl 5'-Monophosphate | EINECS 2
Specifications & Purity≥95%
Biochemical and Physiological MechanismsA 5'- phosphorylated analog of cell permeable AICAR that mimics adenosine monophosphate (AMP). It is an adenylate activated protein kinase (AMPK) activator. In humans, 5-aminoimidazole-4-formamide-1- β—— D-furosyl 5 '- monophosphate (AICAR) has been foun
Storage TempStore at -20°C,Argon charged
Shipped InIce chest + Ice pads
Product Description

AICA-Riboside, 5′-Phosphate is a monophosphorylated analog of the membrane permeable AICA-Riboside that mimics AMP and behaves as an AMPK (AMP-activated protein kinase) activator. AICA-Riboside, 5′-Phosphate displays similar effects of its parent derivative including stimulating glucose transport in certain skeletal-muscle cell lines.

5-aminoimidazole-4-formamide-1-β-d-ribofuran 5 '-monophosphate (AICAR) is a natural metabolic intermediate in purine biosynthesis, commonly found in all organisms. It is produced by succinyl-Aicar (SAICAR) with the help of adenylate succinase (ASL).

Application:

5-aminoimidazole-4-formamide-1-β-D-ribofuranyl 5 '-monophosphate was used in the study to explore the anticancer effects of nine statins in breast cancer and glioblastoma; AICAR monophosphate is a 5 "-phosphorylated analog of cellular permeable AICAR that mimics AMP. AICAR is an adenosine monophosphate (AMP) activated protein kinase (AMPK) activator/agonist.

Associated Targets(Human)

FBP1 Tchem Fructose-1,6-bisphosphatase 1 (0 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
CASP9 Tchem Caspase-9 (0 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
HSP90AA1 Tchem Heat shock protein HSP 90-alpha (0 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
HINT1 Tchem Histidine triad nucleotide-binding protein 1 (0 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
CASP3 Tchem Caspase-3 (0 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
ATIC Tchem Bifunctional purine biosynthesis protein PURH (0 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
CASP3 Tchem Caspase-3 (3632 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ATIC Tchem AICAR transformylase (241 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FBP1 Tchem Fructose-1,6-bisphosphatase (1199 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CASP9 Tchem Caspase-9 (154 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
5637 (630 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A 172 (535 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A204 (242 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A2058 (690 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A-375 (9258 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A-427 (643 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A498 (42825 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A673 (619 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ACHN (49357 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AGS (1999 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BT-20 (503 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BT-474 (2113 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BXPC-3 (2997 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
C8166 (1658 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CAKI-1 (44928 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Calu-3 (339 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Calu-6 (398 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CAPAN-1 (772 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCRF-CEM (65223 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CFPAC-1 (421 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
COR-L23 (253 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Daoy (570 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DMS-79 (150 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DMS-273 (14108 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DU-145 (51482 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
G-361 (890 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
G-401 (156 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HL-60 (67320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HT-1080 (3966 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HT-29 (80576 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HuCCT-1 (128 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Huh-7 (12904 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HuTu80 (255 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
J82 (505 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
JAR (316 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
K562 (73714 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KM12 (47707 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LoVo (4724 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
M14 (47487 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-361 (612 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-453 (1139 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MG-63 (795 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H1975 (4994 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MKN-1 (175 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MKN-28 (466 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

3T3-L1 (3664 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P388 (20296 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
H4 (48 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Names and Identifiers

IUPAC Name [(2R,3S,4R,5R)-5-(5-amino-4-carbamoylimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
INCHI InChI=1S/C9H15N4O8P/c10-7-4(8(11)16)12-2-13(7)9-6(15)5(14)3(21-9)1-20-22(17,18)19/h2-3,5-6,9,14-15H,1,10H2,(H2,11,16)(H2,17,18,19)/t3-,5-,6-,9-/m1/s1
InChi Key NOTGFIUVDGNKRI-UUOKFMHZSA-N
Canonical SMILES C1=NC(=C(N1C2C(C(C(O2)COP(=O)(O)O)O)O)N)C(=O)N
Isomeric SMILES C1=NC(=C(N1[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O)N)C(=O)N
WGK Germany 3
PubChem CID 65110
Molecular Weight 338.21

Certificates

Certificate of Analysis(COA)

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5 results found

Lot NumberCertificate TypeDateItem
B2423657Certificate of AnalysisJan 16, 2024 A346730
B2423659Certificate of AnalysisJan 16, 2024 A346730
B2423666Certificate of AnalysisJan 16, 2024 A346730
B2423668Certificate of AnalysisJan 16, 2024 A346730
B2423671Certificate of AnalysisJan 16, 2024 A346730

Chemical and Physical Properties

SolubilitySoluble in water (partly miscible), DMSO, and methanol.
SensitivityMoisture sensitive
Refractive Indexn20D1.83 (Predicted)
Boil Point(°C)~845.3° C at 760 mmHg (Predicted)
Melt Point(°C)>160° C (dec.)

Safety and Hazards(GHS)

WGK Germany 3

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