Common NameImp
DescriptionInosinic acid, also known as inosine monophosphate, IMP, 5'-inosinate or 5'-IMP, belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. IMP is also classified as a nucleotide (a nucleoside monophosphate). Inosinic acid exists in all living species, ranging from bacteria to plants to humans. IMP is widely used as a flavor enhancer. In the food industry it is known as E number reference E630. Inosinic acid can be converted into various salts including disodium inosinate (E631), dipotassium inosinate (E632), and calcium inosinate (E633). These three inosinate compounds are used as flavor enhancers for the basic taste umami. These inosinate salts are mostly used in soups, sauces, and seasonings for the intensification and balance of the flavor of meat. Inosinic acid is typically obtained from chicken byproducts or other meat industry waste. Inosinic acid or IMP is important in metabolism. It is the ribonucleotide of hypoxanthine and the first nucleotide formed during the synthesis of purine nucleotides. It can also be formed by the deamination of adenosine monophosphate by AMP deaminase. GMP is formed by the inosinate oxidation to xanthylate (XMP). Within humans, inosinic acid participates in a number of enzymatic reactions. In particular, inosinic acid can be converted into phosphoribosyl formamidocarboxamide; which is catalyzed by the bifunctional purine biosynthesis protein. In addition, inosinic acid can be converted into xanthylic acid; which is catalyzed by the enzyme inosine-5'-monophosphate dehydrogenase 1.
Structure
Molecular FormulaC10H13N4O8P
Average Mass348.20600
Monoisotopic Mass348.04710
IUPAC Name{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-oxo-6,9-dihydro-1H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid
Traditional Name[(2r,3s,4r,5r)-3,4-dihydroxy-5-(6-oxo-1h-purin-9-yl)oxolan-2-yl]methoxyphosphonic acid
CAS Registry Number131-99-7
SMILESO=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](COP(=O)([O-])[O-])[C@@H](O)[C@H]1O
InChI IdentifierInChI=1S/C10H13N4O8P/c15-6-4(1-21-23(18,19)20)22-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)17/h2-4,6-7,10,15-16H,1H2,(H,11,12,17)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
InChI KeyGRSZFWQUAKGDAV-KQYNXXCUSA-N
CHEBI IDCHEBI:58053
HMDB IDHMDB0000175
Pathways
NameSMPDB/PathBank
Purine metabolism
Aspartate Metabolism
Adenosine Deaminase Deficiency
Adenylosuccinate Lyase Deficiency
AICA-Ribosiduria
Canavan Disease
Hypoacetylaspartia
Molybdenum Cofactor Deficiency
Purine Nucleoside Phosphorylase Deficiency
Xanthine Dehydrogenase Deficiency (Xanthinuria)
Lesch-Nyhan Syndrome (LNS)
Gout or Kelley-Seegmiller Syndrome
Azathioprine Action Pathway
Mercaptopurine Action Pathway
Thioguanine Action Pathway
Xanthinuria type I
Xanthinuria type II
Adenine phosphoribosyltransferase deficiency (APRT)
Mitochondrial DNA depletion syndrome
Myoadenylate deaminase deficiency
StateSolid
Water Solubility3.05e+00 g/l
logP-2.04
logS-2.06
pKa (Strongest Acidic)1.32
pKa (Strongest Basic)0.51
Hydrogen Acceptor Count9
Hydrogen Donor Count5
Polar Surface Area175.73 Ų
Rotatable Bond Count4
Physiological Charge-2
Formal Charge0
Refractivity72.20 m³·mol⁻¹
Polarizability29.14

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