PRODUCTS

INOSINIC ACID

CAS NUMBER: 131-99-7

EC NUMBER: 205-045-1

MOLECULAR FORMULA: C10H13N4O8P

MOLECULAR WEIGHT: 348.21

IUPAC NAME: [(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-oxo-1H-purin-9-yl)oxolan-2-yl]methyl dihydrogen phosphate

Inosinic Acid or inosine monophosphate (IMP) is a nucleotide (that is, a nucleoside monophosphate).
Widely used as a flavor enhancer, Inosinic Acid is typically obtained from chicken byproducts or other meat industry waste.

Inosinic acid is important in metabolism.
Inosinic Acid is the ribonucleotide of hypoxanthine and the first nucleotide formed during the synthesis of purine nucleotides.

Inosinic Acid can also be formed by the deamination of adenosine monophosphate by AMP deaminase.
Inosinic Acid can be hydrolysed to inosine.

The enzyme deoxyribonucleoside triphosphate pyrophosphohydrolase, encoded by YJR069C in Saccharomyces cerevisiae and containing (d)ITPase and (d)XTPase activities, hydrolyzes inosine triphosphate (ITP) releasing pyrophosphate and IMP.
Important derivatives of inosinic acid include the purine nucleotides found in nucleic acids and adenosine triphosphate, which is used to store chemical energy in muscle and other tissues.

In the food industry, inosinic acid and its salts such as disodium inosinate are used as flavor enhancers.
Inosinic Acid is known as E number reference E630.

Inosinate Synthesis:
The inosinate synthesis is complex, beginning with a 5-phosphoribosyl-1-pyrophosphate (PRPP).
Enzymes taking part in IMP synthesis constitute a multienzyme complex in the cell.
Evidence demonstrates that there are multifunctional enzymes, and some of them catalyze non-sequential steps in the pathway

Synthesis of other purine nucleotides:
Within a few steps inosinate becomes AMP or GMP.
Both compounds are RNA nucleotides.
AMP differs from inosinate by the replacement of IMP's carbon-6 carbonyl with an amino group.
The interconversion of AMP and IMP occurs as part of the purine nucleotide cycle.
GMP is formed by the inosinate oxidation to xanthylate (XMP), and afterwards adds an amino group on carbon 2.
Hydrogen acceptor on inosinate oxidation is NAD+. Finally, carbon 2 gains the amino group by spending an ATP molecule (which becomes AMP+2Pi).
While AMP synthesis requires GTP, GMP synthesis uses ATP.
That difference offers an important regulation possibility.

Regulation of purine nucleotide biosynthesis:
Inosinate and many other molecules inhibit the synthesis of 5-phosphoribosylamine from 5-phosphoribosyl-1-pyrophosphate (PRPP), disabling the enzyme that catalyzes the reaction: glutamine-5-phosphoribosyl-1-pyrophosphate-amidotransferase.
In other words, when levels of inosinate are high, glutamine-5-phosphoribosyl-1-pyrophosphate-amidotransferase is inhibited, and, as a consequence, inosinate levels decrease.
Also, as a result, adenylate and guanylate are not produced, which means that RNA synthesis cannot be completed because of the lack of these two important RNA nucleotides.

Applications:
Inosinic Acid can be converted into various salts including disodium inosinate (E631), dipotassium inosinate (E632), and calcium inosinate (E633).
These three compounds are used as flavor enhancers for the basic taste umami with a comparatively high effectiveness.
They are mostly used in soups, sauces, and seasonings for the intensification and balance of the flavor of meat.

Inosinic Acid inhibits phosphoribosyl pyrophosphate conversion in purine nucleotide synthesis, conversion of inosinic acid to xanthylic acid by purine nucleoside phosphorylase, and incorporation of nucleotide triphosphates into DNA.
Inosinic Acid is a compound important in metabolism.

Inosinic Acid is the ribonucleotide of hypoxanthine and is the first compound formed during the synthesis of purine in organisms.
From inosinic acid are derived such important compounds as the purine nucleotides found in nucleic acids and the energy-rich purine nucleotide adenosine triphosphate, in which chemical energy is stored in cells.
Inosinic acid is a natural product found in Escherichia coli, Schizosaccharomyces pombe, and other organisms with data available.

IMP is a purine ribonucleoside 5'-monophosphate having hypoxanthine as the nucleobase.
Inosinic Acid has a role as a human metabolite, an Escherichia coli metabolite and a mouse metabolite.

Inosinic Acid is a purine ribonucleoside 5'-monophosphate and an inosine phosphate.
Inosinic Acid is a conjugate acid of an IMP(2-).
Inosinic Acid is a purine nucleotide which has hypoxanthine as the base and one phosphate group esterified to the sugar moiety.

Alternative Classes:
-Pentose phosphates
-Glycosylamines
-6-oxopurines
-Hypoxanthines
-Monosaccharide phosphates
-Pyrimidones
-Monoalkyl phosphates
-N-substituted imidazoles
-Heteroaromatic compounds
-Tetrahydrofurans
-Vinylogous amides
-1,2-diols
-Lactams
-Secondary alcohols
-Oxacyclic compounds
-Azacyclic compounds
-Organic oxides
-Organopnictogen compounds
-Hydrocarbon derivatives
-Organonitrogen compounds

Inosinic Acid, also known as 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.

Inosinic Acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Inosinic Acid exists in all living species, ranging from bacteria to humans.

Within humans, Inosinic Acid participates in a number of enzymatic reactions.
In particular, Inosinic Acid can be converted into phosphoribosyl formamidocarboxamide through the action of the enzyme bifunctional purine biosynthesis protein purh.
In addition, Inosinic Acid can be converted into xanthylic acid through its interaction with the enzyme inosine-5'-monophosphate dehydrogenase 1.

PHYSCIAL PROPERTIES:

-Molecular Weight: 348.21

-XLogP3: -3

-Exact Mass: 348.04710038

-Monoisotopic Mass: 348.04710038

-Topological Polar Surface Area: 176 Å²

-Physical Description: Odourless, colourless or white crystals or powder/Solid

-Color: Colorless/White crystals

-Odor: Odourless

-Form: Crystal/Solid

-Solubility: Freely soluble in water, slightly soluble in ethanol

-pH: 1,0-2,0

-pKa: 2.4

-Collision Cross Section: 170.4 Å²

-Refractivity: 72.2 m³·mol⁻¹

-Polarizability: 29.14 Å³

In humans, Inosinic Acid is involved in the metabolic disorder called the gout or kelley-seegmiller syndrome pathway.
Inosinic acid is an odorless tasting compound.

Outside of the human body, Inosinic acid has been detected, but not quantified in, several different foods, such as hickory nuts, turnips, pepper (spice), mountain yams, and muskmelons.
This could make inosinic acid a potential biomarker for the consumption of these foods.

Inosinic Acid is a purine ribonucleoside 5'-monophosphate having hypoxanthine as the nucleobase.
Inosinic Acid 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.

CHEMICAL PROPERTIES:

-Hydrogen Bond Donor Count: 5

-Hydrogen Bond Acceptor Count: 10

-Rotatable Bond Count: 4

-Heavy Atom Count: 23

-Formal Charge: 0

-Complexity: 555

-Isotope Atom Count: 0

-Defined Atom Stereocenter Count: 4

-Undefined Atom Stereocenter Count: 0

-Defined Bond Stereocenter Count: 0

-Undefined Bond Stereocenter Count: 0

-Covalently-Bonded Unit Count: 1

-Compound Is Canonicalized: Yes

Substituents:
-Purine ribonucleoside monophosphate
-Pentose phosphate
-Pentose-5-phosphate
-Glycosyl compound
-N-glycosyl compound
-6-oxopurine
-Hypoxanthine
-Monosaccharide phosphate
-Pentose monosaccharide
-Imidazopyrimidine
-Purine
-Pyrimidone
-Monoalkyl phosphate
-Alkyl phosphate
-Pyrimidine
-Phosphoric acid ester
-Organic phosphoric acid derivative
-N-substituted imidazole
-Monosaccharide
-Tetrahydrofuran
-Vinylogous amide
-Azole
-Imidazole
-Heteroaromatic compound
-Secondary alcohol
-1,2-diol
-Lactam
-Organoheterocyclic compound
-Azacycle
-Oxacycle
-Alcohol
-Organic oxide
-Organopnictogen compound
-Organic oxygen compound
-Organic nitrogen compound
-Organooxygen compound
-Organonitrogen compound
-Hydrocarbon derivative
-Aromatic heteropolycyclic compound

Inosinic Acid is a nucleotide C10H13N4O8P that is found in muscle and is formed by deamination of AMP and that yields hypoxanthine, ribose, and phosphoric acid on hydrolysis
Inosinic Acid is called also IMP.

Inosinic Acid is a purine nucleotide which has hypoxanthine as the base and one phosphate group esterified to the sugar moiety.
Inosinic Acid is a nucleotide present in muscle and other tissues.

Inosinic Acid is formed by the deamination of AMP and when hydrolysed produces inosine.
Inosinic Acid is the ribonucleotide of hypoxanthine and is the first compound formed during the synthesis of purine.
Inosine 5′-monophosphate (IMP) is used as a substrate to study the distribution, specificity and kinetics of inosine-5′-monophosphate dehydrogenase (IMPDH).

Inosinic Acid can also be formed by the deamination of adenosine monophosphate by AMP deaminase.
Inosinic Acid can be hydrolysed to inosine.

Inosinic Acid is important in metabolism.
Inosinic Acid is the ribonucleotide of hypoxanthine and the first nucleotide formed during the synthesis of purine nucleotides.

Inosinic Acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Inosinic Acid exists in all living species, ranging from bacteria to humans.

SYNONYMS:

Inosinic acid
5'-inosinic acid
inosine 5'-monophosphate
inosine monophosphate
5'-IMP
5'-inosinate
IMP
inosine 5'-phosphate
INOSINE-5'-MONOPHOSPHATE
5'-inosine monophosphate
Inosine-5'-monophosphoric acid
Inosine 5'-Monophosphoric acid
I-5'-P
ribosylhypoxanthine monophosphate
[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxypurin-9-yl)oxolan-2-yl]methyl dihydrogen phosphate
((2R,3S,4R,5R)-3,4-Dihydroxy-5-(6-hydroxy-9H-purin-9-yl)tetrahydrofuran-2-yl)methyl dihydrogen phosphate
[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-oxo-6,9-dihydro-3H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid
inosinsaure
Cytosine inosinate
Inosine 5' monophosphate
[3h]inosine monophosphate
Poly(5'-Inosinic acid)
bmse000175
SCHEMBL19255
2'-inosine-5'-monophosphate
GTPL5124
hypoxanthosine 5'-monophosphate
Inosine 5'-(dihydrogen phosphate)
[(2R,3S,4R,5R)-3,4-Dihydroxy-5-(6-oxo-1H-purin-9-yl)oxolan-2-yl]methyl dihydrogen phosphate
ZINC4228242
9-(5-O-Phosphonopentofuranosyl)-9H-purin-6-ol
131I997
Inosine 5 inverted exclamation marka-monophosphate
A1-01972
W-108320
Q27074273
BB128E2C-BC89-4360-B0A0-190DDF5C0B57
[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-oxo-3H-purin-9-yl)oxolan-2-yl]methyl dihydrogen
[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-oxo-1H-purin-9-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate
[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-9H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid
[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-oxo-6,9-dihydro-1H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid