Identification
ECMDB ID: ECMDB04085
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: Thumb
Download: MOL | SDF | SMILES | InChI
Synonyms:
  • 5'-IMP
  • 5'-Inosinate
  • 5'-Inosine monophosphate
  • 5'-Inosinic acid
  • IMP
  • Inosinate
  • Inosine 5'-monophosphate
  • Inosine 5'-phosphate
  • Inosine Monophosphate
  • Inosine-5'-monophosphate
  • Inosine-5'-phosphate
  • Inosinic acid
  • Ribosylhypoxanthine monophosphate
Chemical Formula:
C10H13N4O8P
Weight: Average: 348.206
Monoisotopic: 348.047099924
InChI Key: InChIKey=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
Plain Text
CAS number: 131-99-7
IUPAC Name:
{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-9H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name:
[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxypurin-9-yl)oxolan-2-yl]methoxyphosphonic acid
SMILES:
[H][C@]1(COP(O)(O)=O)O[C@@]([H])(N2C=NC3=C2N=CN=C3O)[C@]([H])(O)[C@]1([H])O
Plain Text
Chemical Taxonomy
Kingdom: Organic Compounds
Super Class: Nucleosides, Nucleotides, and Analogues
Class: Purine Nucleotides
Sub Class: Purine Ribonucleotides
Other Descriptors:
  • Aromatic Heteropolycyclic Compounds
  • purine ribonucleoside 5'-monophosphate(ChEBI)
  • inosine phosphate(ChEBI)
Substituents:
  • Pyrimidine
  • Oxolane
  • Aromatic compound
  • Secondary alcohol
  • 1,2-Diol
  • Imidazole
  • Pentose monosaccharide
  • Monosaccharide phosphate
  • Purine
  • Imidazopyrimidine
  • Saccharide
  • Phosphoric acid ester
  • Organic phosphite
  • Organic hypophosphite
  • Hypoxanthine
  • 1-Phosphoribosyl-imidazole
Direct Parent: Purine Ribonucleoside Monophosphates
Physical Properties
State: Solid
Charge: 0
Melting point: Not Available
Experimental Properties:
Property Value Source
LogP: -2.824 PhysProp
Predicted Properties:
Property Value Source
Water Solubility: 3.60e+00 g/l ALOGPS
LogP: -2.06 ALOGPS
LogP: -3.27 ChemAxon Molconvert
LogS: -1.99 ALOGPS
pKa: 6.3 ChemAxon Molconvert
Hydrogen Acceptor Count: 10 ChemAxon Molconvert
Hydrogen Donor Count: 5 ChemAxon Molconvert
Polar Surface Area: 180.28 A2 ChemAxon Molconvert
Rotatable Bond Count: 4 ChemAxon Molconvert
Refractivity: 71.3 ChemAxon Molconvert
Polarizability: 29.2 ChemAxon Molconvert
Biological Properties
Cellular Locations:
  • Cytosol
  • Extra-organism
  • Periplasm
Pathways:
Ecocyc Pathways:
  • adenine and adenosine salvage III PWY-6609 Link_out
  • adenine and adenosine salvage V PWY-6611 Link_out
  • adenosine nucleotides de novo biosynthesis PWY-6126 Link_out
  • guanosine nucleotides de novo biosynthesis PWY-6125 Link_out
  • inosine-5'-phosphate biosynthesis I PWY-6123 Link_out
Concentrations
Concentration 113 uM
452000 molecules per cell
Strain BW25113
Media 48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco
Growth Status Stationary Phase, glucose limited
Growth System Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h
Temperature 37 oC
Citation Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776 Link_out
Comment
Concentration 272 uM
1088000 molecules per cell
Strain K12 NCM3722
Media Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose
Growth Status Mid-Log Phase
Growth System Shake flask and filter culture
Temperature 37 oC
Citation Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621 Link_out
Comment
Spectra
1H NMR Spectrum view
MS/MS Spectrum Quattro_QQQ 10 view
MS/MS Spectrum Quattro_QQQ 25 view
MS/MS Spectrum Quattro_QQQ 40 view
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) view
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) view
MS/MS Spectrum GC-MS view
[1H,1H] 2D NMR Spectrum view
[1H,13C] 2D NMR Spectrum view
References
References:
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882 Link_out
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Link_out
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195 Link_out
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064 Link_out
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621 Link_out
  • Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776 Link_out
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.
External Links:
Resource Link
CHEBI ID: 17202 Link_out
HMDB ID: HMDB00175 Link_out
Pubchem Compound ID: 8582 Link_out
Kegg ID: C00130 Link_out
ChemSpider ID: 8264 Link_out
Wikipedia: Inosinic acid Link_out
BioCyc ID: IMP Link_out
EcoCyc ID: IMP Link_out
Ligand Expo: IMP Link_out

Enzymes
Name: Protein ushA
Reactions:
Gene Name: ushA Link_out
Uniprot ID: P07024 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Adenylosuccinate synthetase
Reactions:
Gene Name: purA Link_out
Uniprot ID: P0A7D4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Multifunctional protein surE
Reactions:
Gene Name: surE Link_out
Uniprot ID: P0A840 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 5'-nucleotidase yjjG
Reactions:
Gene Name: yjjG Link_out
Uniprot ID: P0A8Y1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hypoxanthine phosphoribosyltransferase
Reactions:
Gene Name: hpt Link_out
Uniprot ID: P0A9M2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Xanthine phosphoribosyltransferase
Reactions:
Gene Name: gpt Link_out
Uniprot ID: P0A9M5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Inosine-5'-monophosphate dehydrogenase
Reactions:
Gene Name: guaB Link_out
Uniprot ID: P0ADG7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Class B acid phosphatase
Reactions:
Gene Name: aphA Link_out
Uniprot ID: P0AE22 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Inosine-guanosine kinase
Reactions:
Gene Name: gsk Link_out
Uniprot ID: P0AEW6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protein mazG
Reactions:
Gene Name: mazG Link_out
Uniprot ID: P0AEY3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Bifunctional purine biosynthesis protein purH
Reactions:
Gene Name: purH Link_out
Uniprot ID: P15639 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside-triphosphatase rdgB
Reactions:
Gene Name: rdgB Link_out
Uniprot ID: P52061 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GMP reductase
Reactions:
Gene Name: guaC Link_out
Uniprot ID: P60560 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 5'-nucleotidase yfbR
Reactions:
Gene Name: yfbR Link_out
Uniprot ID: P76491 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA

Transporters
Name: Outer membrane protein N
Transports:
Gene Name: ompN Link_out
Uniprot ID: P77747 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Outer membrane pore protein E
Transports:
Gene Name: phoE Link_out
Uniprot ID: P02932 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Outer membrane protein F
Transports:
Gene Name: ompF Link_out
Uniprot ID: P02931 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Outer membrane protein C
Transports:
Gene Name: ompC Link_out
Uniprot ID: P06996 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA