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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-05-23 15:43:39 UTC
Update Date2017-12-07 01:59:24 UTC
HMDB IDHMDB0006555
Secondary Accession Numbers
  • HMDB06555
Metabolite Identification
Common NamedIMP
DescriptiondIMP is a deoxyribonucleoside and is considered a derivative of the nucleoside inosine, differing from the latter by the replacement of a hydroxyl group (-OH) by hydrogen (-H) at the 2' position of its ribose sugar moiety. The hydrolytic deamination of dAMP residues in DNA yields dIMP residues. The deamination of adenine residues in DNA generates hypoxanthine, which is mutagenic since it can pair not only with thymine but also with cytosine and therefore would result in A-T to G-C transitions after DNA replication. Hypoxanthine DNA glycosylase (EC 3.2.2.15) excises hypoxanthine from DNA containing dIMP residues in mammalian cells. (PMID: 10684927 , 8016081 ).
Structure
Thumb
Synonyms
ValueSource
2'-Deoxy-5'-inosinic acidChEBI
2'-Deoxyinosine 5'-monophosphateChEBI
2'-Deoxyinosine 5'-monophosphoric acidChEBI
2'-Deoxyinosine 5'-phosphateChEBI
9-(2-Deoxy-5-O-phosphono-beta-D-erythro-pentofuranosyl)-9H-purin-6-olChEBI
9-(2-Deoxy-5-O-phosphono-beta-delta-erythro-pentofuranosyl)-9H-purin-6-olChEBI
Deoxyinosine monophosphateChEBI
2'-Deoxy-5'-inosinateGenerator
2'-Deoxyinosine 5'-phosphoric acidGenerator
9-(2-Deoxy-5-O-phosphono-b-D-erythro-pentofuranosyl)-9H-purin-6-olGenerator
9-(2-Deoxy-5-O-phosphono-β-D-erythro-pentofuranosyl)-9H-purin-6-olGenerator
9-(2-Deoxy-5-O-phosphono-b-delta-erythro-pentofuranosyl)-9H-purin-6-olGenerator
9-(2-Deoxy-5-O-phosphono-β-δ-erythro-pentofuranosyl)-9H-purin-6-olGenerator
Deoxyinosine monophosphoric acidGenerator
9-(2-Deoxy-5-O-phosphono-b-δ-erythro-pentofuranosyl)-9H-purin-6-olGenerator
Hypoxanthine deoxyribosideHMDB
[(2R,3S,4R,5R)-3-Hydroxy-5-(6-hydroxy-9H-purin-9-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphateHMDB
Deoxy impMeSH
Chemical FormulaC10H13N4O7P
Average Molecular Weight332.2066
Monoisotopic Molecular Weight332.052185302
IUPAC Name{[(2R,3S,5R)-3-hydroxy-5-(6-oxo-6,9-dihydro-3H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid
Traditional Name[(2R,3S,5R)-3-hydroxy-5-(6-oxo-3H-purin-9-yl)oxolan-2-yl]methoxyphosphonic acid
CAS Registry Number3393-18-8
SMILES
O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)N1C=NC2=C1NC=NC2=O
InChI Identifier
InChI=1S/C10H13N4O7P/c15-5-1-7(21-6(5)2-20-22(17,18)19)14-4-13-8-9(14)11-3-12-10(8)16/h3-7,15H,1-2H2,(H,11,12,16)(H2,17,18,19)/t5-,6+,7+/m0/s1
InChI KeyPHNGFPPXDJJADG-RRKCRQDMSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside monophosphates. These are purine nucleotides with monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine deoxyribonucleotides
Direct ParentPurine 2'-deoxyribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine 2'-deoxyribonucleoside monophosphate
  • Hypoxanthine
  • Imidazopyrimidine
  • Purine
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.1 g/LALOGPS
logP-1.6ALOGPS
logP-2.6ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)2.77ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area155.5 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity70.26 m³·mol⁻¹ChemAxon
Polarizability27.21 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-001i-9210000000-53948c1a90a0f6914597View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-9210000000-53948c1a90a0f6914597View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9401000000-3e05abb6a8d8b1a335b6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00rx-7923000000-8831273c387905273e72View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-001r-0619000000-1a0eb2cb24a05602189fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-000i-2902000000-8031212ff8d5a3caf932View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-005j-9803000000-e0eccae074a61767e080View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-005j-9803000000-e0eccae074a61767e080View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001r-0619000000-1a0eb2cb24a05602189fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-2902000000-8031212ff8d5a3caf932View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0901000000-82485bc6f5afd265ffb6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-40c3e510e6f14b9c6415View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0900000000-084491e4ef779439c6e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-5209000000-fe97448e2adad18be4e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-9400000000-69f08fb1d6025455e334View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-eaad95f8c8f37f17a06dView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023969
KNApSAcK IDNot Available
Chemspider ID82650
KEGG Compound IDC06196
BioCyc IDDIMP
BiGG ID47635
Wikipedia LinkDeoxyinosine_monophosphate
METLIN IDNot Available
PubChem Compound91531
PDB IDDI
ChEBI ID28806
References
Synthesis ReferenceOgilvie, Kelvin K.; Slotin, Lewis A. Anhydronucleosides. XI. Synthesis of nucleotides from 8,2'-thioanhydropurine nucleosides. Canadian Journal of Chemistry (1973), 51(14), 2397-405.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Saparbaev M, Mani JC, Laval J: Interactions of the human, rat, Saccharomyces cerevisiae and Escherichia coli 3-methyladenine-DNA glycosylases with DNA containing dIMP residues. Nucleic Acids Res. 2000 Mar 15;28(6):1332-9. [PubMed:10684927 ]
  2. Saparbaev M, Laval J: Excision of hypoxanthine from DNA containing dIMP residues by the Escherichia coli, yeast, rat, and human alkylpurine DNA glycosylases. Proc Natl Acad Sci U S A. 1994 Jun 21;91(13):5873-7. [PubMed:8016081 ]

Enzymes

General function:
Involved in phosphatase activity
Specific function:
Dephosphorylates specifically the 5' and 2'(3')-phosphates of uracil and thymine deoxyribonucleotides, and so protects mitochondrial DNA replication from excess dTTP. Has only marginal activity towards dIMP and dGMP.
Gene Name:
NT5M
Uniprot ID:
Q9NPB1
Molecular weight:
Not Available
General function:
Involved in hydrolase activity
Specific function:
Pyrophosphatase that hydrolyzes the non-canonical purine nucleotides inosine triphosphate (ITP), deoxyinosine triphosphate (dITP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) and xanthosine 5'-triphosphate (XTP) to their respective monophosphate derivatives. The enzyme does not distinguish between the deoxy- and ribose forms. Probably excludes non-canonical purines from RNA and DNA precursor pools, thus preventing their incorporation into RNA and DNA and avoiding chromosomal lesions.
Gene Name:
ITPA
Uniprot ID:
Q9BY32
Molecular weight:
16833.23
Reactions
2'-Deoxyinosine triphosphate + Water → dIMP + Pyrophosphatedetails