Inosinic acid (ECMDB04085) (M2MDB000601)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 14:04:30 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-09-13 12:56:13 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | Inosinic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | Inosinic acid is a purine nucleotide which has hypoxanthine as the base and one phosphate group esterified to the sugar moiety. It 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. (Wikipedia) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| Chemical Formula: | C10H13N4O8P | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 348.206 Monoisotopic: 348.047099924 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | GRSZFWQUAKGDAV-KQYNXXCUSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI: | InChI=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 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | 131-99-7 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 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 IUPAC Name: | inosine-5'-monophosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=CNC2=O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | 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. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Nucleosides, nucleotides, and analogues | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Purine nucleotides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Purine ribonucleotides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | Purine ribonucleoside monophosphates | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Alternative Parents |
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| Substituents |
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| Molecular Framework | Aromatic heteropolycyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
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| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge: | -2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
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| Predicted Properties |
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| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: | Hypoxanthine + Phosphoribosyl pyrophosphate <> Inosinic acid + Pyrophosphate Water + Inosinic acid > Inosine + Phosphate Guanosine monophosphate + 2 Hydrogen ion + NADPH > Inosinic acid + NADP + Ammonium Adenosine triphosphate + Inosine <> ADP + Hydrogen ion + Inosinic acid Water + Inosinic acid + NAD <> Hydrogen ion + NADH + Xanthylic acid Water + Inosine triphosphate > Hydrogen ion + Inosinic acid + Pyrophosphate Water + Inosinic acid <> Phosphoribosyl formamidocarboxamide L-Aspartic acid + Guanosine triphosphate + Inosinic acid <> Adenylsuccinic acid + Guanosine diphosphate +2 Hydrogen ion + Phosphate Inosine triphosphate + Water <> Inosinic acid + Pyrophosphate Inosinic acid + Water <> Inosine + Phosphate Adenosine triphosphate + Inosine <> ADP + Inosinic acid Inosinic acid + Pyrophosphate <> Hypoxanthine + Phosphoribosyl pyrophosphate Inosinic acid + Ammonia + NADP <> Guanosine monophosphate + NADPH + Hydrogen ion Guanosine triphosphate + Inosinic acid + L-Aspartic acid <> Guanosine diphosphate + Phosphate + Adenylsuccinic acid L-Aspartic acid + Inosinic acid + Guanosine triphosphate > Hydrogen ion + adenylo-succinate + Phosphate + Guanosine diphosphate Ammonia + Inosinic acid + NADP < Hydrogen ion + Guanosine monophosphate + NADPH Pyrophosphate + Inosinic acid < Phosphoribosyl pyrophosphate + Hypoxanthine Water + NAD + Inosinic acid > Hydrogen ion + NADH + Xanthylic acid Inosine + Adenosine triphosphate > Hydrogen ion + Inosinic acid + ADP Inosinic acid + Ammonia + NADP > Guanosine monophosphate + NADPH Inosinic acid + Pyrophosphate > Hypoxanthine + Phosphoribosyl pyrophosphate Inosinic acid + NAD + Water > Xanthylic acid + NADH Adenosine triphosphate + Inosine > ADP + Inosinic acid Inosinic acid + Water > Phosphoribosyl formamidocarboxamide Guanosine triphosphate + Inosinic acid + L-Aspartic acid > Guanosine diphosphate + Inorganic phosphate + N(6)-(1,2-dicarboxyethyl)AMP Guanosine triphosphate + Inosinic acid + L-Aspartic acid + L-Aspartic acid > Guanosine diphosphate + Phosphate + N(6)-(1,2-dicarboxyethyl)AMP More...Inosinic acid + L-Aspartic acid + Guanosine triphosphate + L-Aspartic acid > Guanosine diphosphate + Phosphate +2 Hydrogen ion + N(6)-(1,2-dicarboxyethyl)AMP + Adenylsuccinic acid FAICAR <> Inosinic acid + Water Hypoxanthine + Phosphoribosyl pyrophosphate > Inosinic acid + Pyrophosphate Water + Inosinic acid + NAD <> Hydrogen ion + NADH + Xanthylic acid Water + Inosinic acid <> Phosphoribosyl formamidocarboxamide L-Aspartic acid + Guanosine triphosphate + Inosinic acid <> Adenylsuccinic acid + Guanosine diphosphate +2 Hydrogen ion + Phosphate Water + Inosinic acid + NAD <> Hydrogen ion + NADH + Xanthylic acid Water + Inosinic acid <> Phosphoribosyl formamidocarboxamide | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMPDB Pathways: |
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| KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| EcoCyc Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Find out more about how we convert literature concentrations. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References: |
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| Synthesis Reference: | Park, Yeong Hun; Cho, Gwang Myeong; Baek, Min Ji; Hong, Guk Gi; Lee, Jin Nam. Method for preparing 5'-inosinic acid by using microbe capable of over-expressing purC gene. Repub. Korea (2007), 7pp. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Enzymes
- General function:
- Involved in hydrolase activity
- Specific function:
- Degradation of external UDP-glucose to uridine monophosphate and glucose-1-phosphate, which can then be used by the cell
- Gene Name:
- ushA
- Uniprot ID:
- P07024
- Molecular weight:
- 60824
Reactions
| UDP-sugar + H(2)O = UMP + alpha-D-aldose 1-phosphate. |
| A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate. |
- General function:
- Involved in adenylosuccinate synthase activity
- Specific function:
- Plays an important role in the de novo pathway of purine nucleotide biosynthesis. Catalyzes the first commited step in the biosynthesis of AMP from IMP
- Gene Name:
- purA
- Uniprot ID:
- P0A7D4
- Molecular weight:
- 47345
Reactions
| GTP + IMP + L-aspartate = GDP + phosphate + N(6)-(1,2-dicarboxyethyl)-AMP. |
- General function:
- Involved in hydrolase activity
- Specific function:
- Nucleotidase with a broad substrate specificity as it can dephosphorylate various ribo- and deoxyribonucleoside 5'- monophosphates and ribonucleoside 3'-monophosphates with highest affinity to 3'-AMP. Also hydrolyzes polyphosphate (exopolyphosphatase activity) with the preference for short-chain- length substrates (P20-25). Might be involved in the regulation of dNTP and NTP pools, and in the turnover of 3'-mononucleotides produced by numerous intracellular RNases (T1, T2, and F) during the degradation of various RNAs. Also plays a significant physiological role in stress-response and is required for the survival of E.coli in stationary growth phase
- Gene Name:
- surE
- Uniprot ID:
- P0A840
- Molecular weight:
- 26900
Reactions
| A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate. |
| A 3'-ribonucleotide + H(2)O = a ribonucleoside + phosphate. |
| (Polyphosphate)(n) + H(2)O = (polyphosphate)(n-1) + phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Nucleotidase that shows high phosphatase activity toward three nucleoside 5'-monophosphates, UMP, dUMP, and dTMP, and very low activity against TDP, IMP, UDP, GMP, dGMP, AMP, dAMP, and 6- phosphogluconate. Is strictly specific to substrates with 5'- phosphates and shows no activity against nucleoside 2'- or 3'- monophosphates. Might be involved in the pyrimidine nucleotide substrate cycles
- Gene Name:
- yjjG
- Uniprot ID:
- P0A8Y1
- Molecular weight:
- 25300
Reactions
| A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate. |
- General function:
- Involved in hypoxanthine phosphoribosyltransferase activity
- Specific function:
- This enzyme acts exclusively on hypoxanthine; it does not act on guanine
- Gene Name:
- hpt
- Uniprot ID:
- P0A9M2
- Molecular weight:
- 20115
Reactions
| IMP + diphosphate = hypoxanthine + 5-phospho-alpha-D-ribose 1-diphosphate. |
- General function:
- Involved in nucleoside metabolic process
- Specific function:
- Acts on guanine, xanthine and to a lesser extent hypoxanthine
- Gene Name:
- gpt
- Uniprot ID:
- P0A9M5
- Molecular weight:
- 16971
Reactions
| XMP + diphosphate = 5-phospho-alpha-D-ribose 1-diphosphate + xanthine. |
- General function:
- Involved in catalytic activity
- Specific function:
- Inosine 5'-phosphate + NAD(+) + H(2)O = xanthosine 5'-phosphate + NADH
- Gene Name:
- guaB
- Uniprot ID:
- P0ADG7
- Molecular weight:
- 52022
Reactions
| Inosine 5'-phosphate + NAD(+) + H(2)O = xanthosine 5'-phosphate + NADH. |
- General function:
- Involved in acid phosphatase activity
- Specific function:
- Dephosphorylates several organic phosphomonoesters and catalyzes the transfer of low-energy phosphate groups from phosphomonoesters to hydroxyl groups of various organic compounds. Preferentially acts on aryl phosphoesters. Might function as a broad-spectrum dephosphorylating enzyme able to scavenge both 3'- and 5'-nucleotides and also additional organic phosphomonoesters
- Gene Name:
- aphA
- Uniprot ID:
- P0AE22
- Molecular weight:
- 26103
Reactions
| A phosphate monoester + H(2)O = an alcohol + phosphate. |
- General function:
- Involved in phosphotransferase activity, alcohol group as acceptor
- Specific function:
- ATP + inosine = ADP + IMP
- Gene Name:
- gsk
- Uniprot ID:
- P0AEW6
- Molecular weight:
- 48448
Reactions
| ATP + inosine = ADP + IMP. |
- General function:
- Involved in nucleoside-triphosphate diphosphatase activity
- Specific function:
- Specific function unknown
- Gene Name:
- mazG
- Uniprot ID:
- P0AEY3
- Molecular weight:
- 30412
Reactions
| ATP + H(2)O = AMP + diphosphate. |
- General function:
- Involved in IMP cyclohydrolase activity
- Specific function:
- 10-formyltetrahydrofolate + 5-amino-1-(5- phospho-D-ribosyl)imidazole-4-carboxamide = tetrahydrofolate + 5- formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide
- Gene Name:
- purH
- Uniprot ID:
- P15639
- Molecular weight:
- 57329
Reactions
| 10-formyltetrahydrofolate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide = tetrahydrofolate + 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide. |
| IMP + H(2)O = 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide. |
- General function:
- Involved in hydrolase activity
- Specific function:
- Hydrolyzes O6 atom-containing purine bases deoxyinosine triphosphate (dITP) and xanthosine triphosphate (XTP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) to nucleotide monophosphate and pyrophosphate. Probably excludes non- standard purines from DNA precursor pool, preventing thus incorporation into DNA and avoiding chromosomal lesions
- Gene Name:
- rdgB
- Uniprot ID:
- P52061
- Molecular weight:
- 21039
Reactions
| A nucleoside triphosphate + H(2)O = a nucleotide + diphosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Catalyzes the irreversible NADPH-dependent deamination of GMP to IMP. It functions in the conversion of nucleobase, nucleoside and nucleotide derivatives of G to A nucleotides, and in maintaining the intracellular balance of A and G nucleotides
- Gene Name:
- guaC
- Uniprot ID:
- P60560
- Molecular weight:
- 37383
Reactions
| Inosine 5'-phosphate + NH(3) + NADP(+) = guanosine 5'-phosphate + NADPH. |
- General function:
- Involved in catalytic activity
- Specific function:
- Nucleotidase that shows strict specificity toward deoxyribonucleoside 5'-monophosphates and does not dephosphorylate 5'-ribonucleotides or ribonucleoside 3'-monophosphates. Might be involved in the regulation of all dNTP pools in E.coli
- Gene Name:
- yfbR
- Uniprot ID:
- P76491
- Molecular weight:
- 22708
Reactions
| A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate. |
Transporters
- General function:
- Involved in transporter activity
- Specific function:
- Non-specific porin
- Gene Name:
- ompN
- Uniprot ID:
- P77747
- Molecular weight:
- 41220
- General function:
- Involved in transporter activity
- Specific function:
- Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
- Gene Name:
- phoE
- Uniprot ID:
- P02932
- Molecular weight:
- 38922
- General function:
- Involved in transporter activity
- Specific function:
- OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
- Gene Name:
- ompF
- Uniprot ID:
- P02931
- Molecular weight:
- 39333
- General function:
- Involved in transporter activity
- Specific function:
- Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
- Gene Name:
- ompC
- Uniprot ID:
- P06996
- Molecular weight:
- 40368