AICA ribonucleotide

Details

• Internal ID: fe74ce34-790f-47c1-8053-2a429e2b4001
• Taxonomy: Nucleosides, nucleotides, and analogues > Imidazole ribonucleosides and ribonucleotides > 1-ribosyl-imidazolecarboxamides
• IUPAC Name: [(2R,3S,4R,5R)-5-(5-amino-4-carbamoylimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
• SMILES (Canonical): C1=NC(=C(N1C2C(C(C(O2)COP(=O)(O)O)O)O)N)C(=O)N
• SMILES (Isomeric): C1=NC(=C(N1[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O)N)C(=O)N
• 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
• Popularity: 1,306 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₅N₄O₈P
• Molecular Weight: 338.21 g/mol
• Exact Mass: 338.06275045 g/mol
• Topological Polar Surface Area (TPSA): 203.00 Ų
• XlogP: -3.80
• Atomic LogP (AlogP): -2.71
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

• 3031-94-5
• Z-nucleotide
• AICAR monophosphate
• 5-amino-4-imidazolecarboxamide ribotide
• aminoimidazole carboxamide ribonucleotide
• 5'-Phosphoribosyl-5-amino-4-imidazolecarboxamide
• Acadesine 5'-monophosphate
• AICA-ribonucleotide
• 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide
• 5-Amino-4-imidazole carboxamide ribonucleotide
• EINECS 221-212-1
• UNII-F0X88YW0YK
• NSC 283955
• NSC 292227
• 5-Aminoimidazole-4-carboxamide ribotide
• F0X88YW0YK
• 5-Amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-1H-imidazole-4-carboxamide
• C9H15N4O8P
• CHEMBL483849
• 5-Amino-4-imidazolecarboxamide ribonucleoside 5'-monophosphate
• 5-Phosphoribosyl-4-carbamoyl-5-aminoimidazole
• CHEBI:18406
• AMINOIMIDAZOLE 4-CARBOXAMIDE RIBONUCLEOTIDE
• 5'-Phospho-ribosyl-5-amino-4-imidazole carboxamide
• 5'-P-ribosyl-5-amino-4-imidazole carboxamide
• 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide
• {[(2R,3S,4R,5R)-5-(5-amino-4-carbamoyl-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
• 5'-phosphoribosyl-5-amino-4-imidazole carboxamide
• Imidazole-4-carboxamide, 5-amino-1-beta-D-ribofuranosyl-, 5'-(dihydrogen phosphate)
• AMZ
• 1H-imidazole-4-carboxamide, 5-amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-
• ZMP
• C9-H15-N4-O8-P
• AICA Ribotide
• NSC-283955
• NSC-292227
• 1H-Imidazole-4-carboxamide, 5-amino-1-(5-O-phosphono-.beta.-D-ribofuranosyl)-
• 5-amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide
• AICAR [MART.]
• AICA-Riboside, 5'-Phosphate
• SCHEMBL1230585
• aminomidazole carboxamide riboside
• BDBM22579
• DTXSID10904363
• Imidazole-4-carboxamide, 5-amino-1-.beta.-D-ribofuranosyl-, 5'-(dihydrogen phosphate)
• DB01700
• AM806773
• Aminoimidazole-4-carboxamide ribonucleotide
• LS-174296
• 5-Amino-4-imidazolecarboxamide ribonucleotide
• C04677
• Q2817102
• W-202250
• 5'-Phospho-b-D-ribosyl-5-amino-4-imidazolecarboxamide
• 5-Amino-1-(5'-phosphofuranoribosyl)-4-imidazolecarboxamide
• 5-Amino-1beta-D-ribofuranosylimidazole-4-carboxamide 5'-phosphate
• 5-Aminoimidazole-4-carboxamide-1-?-D-Ribofuranosyl 5'-Monophosphate
• 5-Aminoimidazole-4-carboxamide-1-b-D-ribofuranose 5'-monophosphate
• 5-Amino-1-(5-O-phosphono-b-D-ribofuranosyl)-1H-imidazole-4-carboxamide
• 5-Aminoimidazole-4-carboxamide-1-.beta.D-ribofuranosyl 5'-monophosphate
• 1H-Imidazole-4-carboxamide, 5-amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-(9Cl)
• 5-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranosyl 5'-monophosphate, >=93%
• Imidazole-4-carboxamide, 5-amino-1-b-D-ribofuranosyl-, 5'-phosphate (6CI,7CI)
• Imidazole-4-carboxamide, 5-amino-1-beta-D-ribofuranosyl-, 5'-(dihydrogen phosphate) (8Cl)
• ((2R,3S,4R,5R)-5-(5-amino-4-carbamoyl-1H-imidazol-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7909	79.09%
Caco-2	-	0.9048	90.48%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.4898	48.98%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9476	94.76%
OATP1B3 inhibitior	+	0.9430	94.30%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9247	92.47%
P-glycoprotein inhibitior	-	0.8514	85.14%
P-glycoprotein substrate	-	0.8403	84.03%
CYP3A4 substrate	+	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8816	88.16%
CYP3A4 inhibition	-	0.9368	93.68%
CYP2C9 inhibition	-	0.9028	90.28%
CYP2C19 inhibition	-	0.8902	89.02%
CYP2D6 inhibition	-	0.9083	90.83%
CYP1A2 inhibition	-	0.8664	86.64%
CYP2C8 inhibition	-	0.8872	88.72%
CYP inhibitory promiscuity	-	0.9850	98.50%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Non-required	0.5401	54.01%
Eye corrosion	-	0.9843	98.43%
Eye irritation	-	0.9701	97.01%
Skin irritation	-	0.7493	74.93%
Skin corrosion	-	0.9240	92.40%
Ames mutagenesis	-	0.7745	77.45%
Human Ether-a-go-go-Related Gene inhibition	-	0.6708	67.08%
Micronuclear	+	0.9900	99.00%
Hepatotoxicity	+	0.7006	70.06%
skin sensitisation	-	0.8181	81.81%
Respiratory toxicity	+	0.9222	92.22%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.8095	80.95%
Acute Oral Toxicity (c)	III	0.6131	61.31%
Estrogen receptor binding	-	0.5654	56.54%
Androgen receptor binding	-	0.6877	68.77%
Thyroid receptor binding	+	0.5451	54.51%
Glucocorticoid receptor binding	-	0.6212	62.12%
Aromatase binding	+	0.7831	78.31%
PPAR gamma	+	0.6286	62.86%
Honey bee toxicity	-	0.7685	76.85%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	-	0.6335	63.35%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3975	P09467	Fructose-1,6-bisphosphatase	12000 nM	IC50	PMID: 19348494

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.96%	96.09%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	95.14%	80.33%
CHEMBL3401	O75469	Pregnane X receptor	88.57%	94.73%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.69%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.63%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.39%	99.17%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	82.77%	87.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.60%	89.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.33%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.64%	95.89%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	80.75%	93.65%

Plants that contains it

• Arabidopsis thaliana

Cross-Links

• PubChem: 65110
• NPASS: NPC30326
• ChEMBL: CHEMBL483849
• LOTUS: LTS0024572
• wikiData: Q2817102