You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2006-08-12 18:44:06 UTC
Update Date2013-02-09 00:12:27 UTC
HMDB IDHMDB03335
Secondary Accession NumbersNone
Metabolite Identification
Common NameIDP
DescriptionIDP is an inosine nucleotide containing a pyrophosphate group esterified to C5 of the sugar moiety.
Structure
Thumb
Synonyms
  1. 5'-IDP
  2. IDP
  3. Inosine 5'-(trihydrogen diphosphate)
  4. Inosine 5'-(trihydrogen pyrophosphate)
  5. Inosine 5'-diphosphate
  6. Inosine 5'-pyrophosphate
  7. Inosine diphosphate
  8. Inosine pyrophosphate
  9. Riboxin
  10. Riboxine
Chemical FormulaC10H14N4O11P2
Average Molecular Weight428.1859
Monoisotopic Molecular Weight428.013430334
IUPAC Name[({[(2R,3S,4R)-3,4-dihydroxy-5-(6-oxo-6,9-dihydro-3H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
Traditional Name{[(2R,3S,4R)-3,4-dihydroxy-5-(6-oxo-3H-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid
CAS Registry Number86-04-4
SMILES
O[C@@H]1[C@@H](COP(O)(=O)OP(O)(O)=O)OC([C@@H]1O)N1C=NC2=C1NC=NC2=O
InChI Identifier
InChI=1S/C10H14N4O11P2/c15-6-4(1-23-27(21,22)25-26(18,19)20)24-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)17/h2-4,6-7,10,15-16H,1H2,(H,21,22)(H,11,12,17)(H2,18,19,20)/t4-,6-,7-,10?/m1/s1
InChI KeyJPXZQMKKFWMMGK-VTHZCTBJSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPurine Nucleotides
Sub ClassPurine Ribonucleotides
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • 1 Phosphoribosyl Imidazole
  • Glycosyl Compound
  • Hypoxanthine
  • Imidazole
  • Imidazopyrimidine
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Purine
  • Purinone
  • Pyrimidine
  • Pyrimidone
  • Saccharide
  • Secondary Alcohol
Direct ParentPurine Ribonucleoside Monophosphates
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Extracellular
  • Mitochondria
  • Nucleus
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 Solubility4.26ALOGPS
logP-0.99ALOGPS
logP-3.6ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)2.65ChemAxon
pKa (Strongest Basic)1.73ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area222.26 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity82.64 m3·mol-1ChemAxon
Polarizability33.75 Å3ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
  • Nucleus
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Purine MetabolismSMP00050map00230
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023146
KNApSAcK IDNot Available
Chemspider ID559208
KEGG Compound IDC00104
BioCyc IDIDP
BiGG ID33869
Wikipedia LinkIDP
NuGOwiki LinkHMDB03335
Metagene LinkHMDB03335
METLIN ID6892
PubChem Compound644173
PDB IDNot Available
ChEBI ID17808
References
Synthesis ReferenceTakada, Masao; Kashiwa, Kenichi. Nucleoside 5'-pyrophosphates. Jpn. Tokkyo Koho (1971), 3 pp. CODEN: JAXXAD JP 46021587 19710618 Showa. CAN 75:130076 AN 1971:530076 CAPLUS
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hlushko LV, Makovets'ka TI, Neiko IeM: [The dynamics of the glycocholic acid content of the bile in patients with chronic inactive hepatitis] Lik Sprava. 1995 May-Jun;(5-6):152-4. Pubmed: 8630789

Enzymes

General function:
Involved in calcium ion binding
Specific function:
Calcium-dependent nucleotidase with a preference for UDP. The order of activity with different substrates is UDP > GDP > UTP > GTP. Has very low activity towards ADP and even lower activity towards ATP. Does not hydrolyze AMP and GMP. Involved in proteoglycan synthesis.
Gene Name:
CANT1
Uniprot ID:
Q8WVQ1
Molecular weight:
44839.24
Reactions
IDP + Water → Inosinic acid + Phosphoric aciddetails
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate. Inhibitor of p53-induced apoptosis.
Gene Name:
NME6
Uniprot ID:
O75414
Molecular weight:
22002.965
Reactions
Adenosine triphosphate + IDP → ADP + Inosine triphosphatedetails
General function:
Involved in ATP binding
Specific function:
Catalyzes the initial step in utilization of glucose by the beta-cell and liver at physiological glucose concentration. Glucokinase has a high Km for glucose, and so it is effective only when glucose is abundant. The role of GCK is to provide G6P for the synthesis of glycogen. Pancreatic glucokinase plays an important role in modulating insulin secretion. Hepatic glucokinase helps to facilitate the uptake and conversion of glucose by acting as an insulin-sensitive determinant of hepatic glucose usage.
Gene Name:
GCK
Uniprot ID:
P35557
Molecular weight:
52191.07
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
HK2
Uniprot ID:
P52789
Molecular weight:
102379.06
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
HK3
Uniprot ID:
P52790
Molecular weight:
99024.56
General function:
Involved in 6-phosphofructokinase activity
Specific function:
Catalyzes the third step of glycolysis, the phosphorylation of fructose-6-phosphate (F6P) by ATP to generate fructose-1,6-bisphosphate (FBP) and ADP.
Gene Name:
PFKL
Uniprot ID:
P17858
Molecular weight:
85017.825
Reactions
Inosine triphosphate + D-Tagatose 6-phosphate → IDP + D-Tagatose 1,6-bisphosphatedetails
General function:
Involved in 6-phosphofructokinase activity
Specific function:
Catalyzes the third step of glycolysis, the phosphorylation of fructose-6-phosphate (F6P) by ATP to generate fructose-1,6-bisphosphate (FBP) and ADP.
Gene Name:
PFKM
Uniprot ID:
P08237
Molecular weight:
85181.925
Reactions
Inosine triphosphate + D-Tagatose 6-phosphate → IDP + D-Tagatose 1,6-bisphosphatedetails
General function:
Involved in 6-phosphofructokinase activity
Specific function:
Catalyzes the third step of glycolysis, the phosphorylation of fructose-6-phosphate (F6P) by ATP to generate fructose-1,6-bisphosphate (FBP) and ADP.
Gene Name:
PFKP
Uniprot ID:
Q01813
Molecular weight:
85595.405
Reactions
Inosine triphosphate + D-Tagatose 6-phosphate → IDP + D-Tagatose 1,6-bisphosphatedetails
General function:
Involved in magnesium ion binding
Specific function:
Plays a key role in glycolysis (By similarity).
Gene Name:
PKLR
Uniprot ID:
P30613
Molecular weight:
61829.575
General function:
Involved in ATP binding
Specific function:
May contribute to UTP accumulation needed for blast transformation and proliferation.
Gene Name:
UCKL1
Uniprot ID:
Q9NWZ5
Molecular weight:
59465.77
Reactions
Inosine triphosphate + Cytidine → IDP + Cytidine monophosphatedetails
Inosine triphosphate + Uridine → IDP + Uridine 5'-monophosphatedetails
General function:
Involved in ATP binding
Specific function:
Phosphorylates uridine and cytidine to uridine monophosphate and cytidine monophosphate. Does not phosphorylate deoxyribonucleosides or purine ribonucleosides. Can use ATP or GTP as a phosphate donor. Can also phosphorylate cytidine and uridine nucleoside analogs such as 6-azauridine, 5-fluorouridine, 4-thiouridine, 5-bromouridine, N(4)-acetylcytidine, N(4)-benzoylcytidine, 5-fluorocytidine, 2-thiocytidine, 5-methylcytidine, and N(4)-anisoylcytidine.
Gene Name:
UCK2
Uniprot ID:
Q9BZX2
Molecular weight:
29298.92
Reactions
Inosine triphosphate + Cytidine → IDP + Cytidine monophosphatedetails
Inosine triphosphate + Uridine → IDP + Uridine 5'-monophosphatedetails
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. Possesses nucleoside-diphosphate kinase, serine/threonine-specific protein kinase, geranyl and farnesyl pyrophosphate kinase, histidine protein kinase and 3'-5' exonuclease activities. Involved in cell proliferation, differentiation and development, signal transduction, G protein-coupled receptor endocytosis, and gene expression. Required for neural development including neural patterning and cell fate determination.
Gene Name:
NME1
Uniprot ID:
P15531
Molecular weight:
17148.635
Reactions
Adenosine triphosphate + IDP → ADP + Inosine triphosphatedetails
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. Negatively regulates Rho activity by interacting with AKAP13/LBC. Acts as a transcriptional activator of the MYC gene; binds DNA non-specifically (PubMed:8392752). Exhibits histidine protein kinase activity.
Gene Name:
NME2
Uniprot ID:
P22392
Molecular weight:
30136.92
Reactions
Adenosine triphosphate + IDP → ADP + Inosine triphosphatedetails
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP (By similarity).
Gene Name:
NME4
Uniprot ID:
O00746
Molecular weight:
20658.45
Reactions
Adenosine triphosphate + IDP → ADP + Inosine triphosphatedetails
General function:
Involved in hydrolase activity
Specific function:
Canalicular ectonucleoside NTPDase responsible for the main hepatic NTPDase activity. Ectonucleoside NTPDases catalyze the hydrolysis of gamma- and beta-phosphate residues of nucleotides, playing a central role in concentration of extracellular nucleotides. Has activity toward ATP, ADP, UTP and UDP, but not toward AMP.
Gene Name:
ENTPD8
Uniprot ID:
Q5MY95
Molecular weight:
53903.14
Reactions
Inosine triphosphate + Water → IDP + Phosphoric aciddetails
IDP + Water → Inosinic acid + Phosphoric aciddetails
General function:
Involved in hydrolase activity
Specific function:
In the nervous system, could hydrolyze ATP and other nucleotides to regulate purinergic neurotransmission. Could also be implicated in the prevention of platelet aggregation by hydrolyzing platelet-activating ADP to AMP. Hydrolyzes ATP and ADP equally well.
Gene Name:
ENTPD1
Uniprot ID:
P49961
Molecular weight:
58706.0
Reactions
Inosine triphosphate + Water → IDP + Phosphoric aciddetails
IDP + Water → Inosinic acid + Phosphoric aciddetails
General function:
Involved in hydrolase activity
Specific function:
Not Available
Gene Name:
ENTPD4
Uniprot ID:
Q8NE73
Molecular weight:
64852.9
General function:
Involved in phosphoenolpyruvate carboxykinase activity
Specific function:
Catalyzes the conversion of oxaloacetate (OAA) to phosphoenolpyruvate (PEP), the rate-limiting step in the metabolic pathway that produces glucose from lactate and other precursors derived from the citric acid cycle.
Gene Name:
PCK1
Uniprot ID:
P35558
Molecular weight:
69193.975
Reactions
Inosine triphosphate + Oxalacetic acid → IDP + Phosphoenolpyruvic acid + Carbon dioxidedetails
General function:
Involved in catalytic activity
Specific function:
Catalyzes the GTP-dependent ligation of succinate and CoA to form succinyl-CoA (By similarity).
Gene Name:
SUCLG2
Uniprot ID:
Q96I99
Molecular weight:
47731.605
Reactions
Inosine triphosphate + Succinic acid + Coenzyme A → IDP + Phosphoric acid + Succinyl-CoAdetails
General function:
Involved in catalytic activity
Specific function:
Catalyzes the ATP- or GTP-dependent ligation of succinate and CoA to form succinyl-CoA. The nature of the beta subunit determines the nucleotide specificity (By similarity).
Gene Name:
SUCLG1
Uniprot ID:
P53597
Molecular weight:
36249.505
Reactions
Inosine triphosphate + Succinic acid + Coenzyme A → IDP + Phosphoric acid + Succinyl-CoAdetails
General function:
Involved in magnesium ion binding
Specific function:
Glycolytic enzyme that catalyzes the transfer of a phosphoryl group from phosphoenolpyruvate (PEP) to ADP, generating ATP. Stimulates POU5F1-mediated transcriptional activation. Plays a general role in caspase independent cell death of tumor cells. The ratio betwween the highly active tetrameric form and nearly inactive dimeric form determines whether glucose carbons are channeled to biosynthetic processes or used for glycolytic ATP production. The transition between the 2 forms contributes to the control of glycolysis and is important for tumor cell proliferation and survival.
Gene Name:
PKM
Uniprot ID:
P14618
Molecular weight:
65930.14
General function:
Involved in catalytic activity
Specific function:
Catalyzes the ATP-dependent ligation of succinate and CoA to form succinyl-CoA (By similarity).
Gene Name:
SUCLA2
Uniprot ID:
Q9P2R7
Molecular weight:
50316.88
Reactions
Inosine triphosphate + Succinic acid + Coenzyme A → IDP + Phosphoric acid + Succinyl-CoAdetails
General function:
Involved in hydrolase activity
Specific function:
Has a threefold preference for the hydrolysis of ATP over ADP.
Gene Name:
ENTPD3
Uniprot ID:
O75355
Molecular weight:
59104.76
Reactions
Inosine triphosphate + Water → IDP + Phosphoric aciddetails
IDP + Water → Inosinic acid + Phosphoric aciddetails
General function:
Involved in hydrolase activity
Specific function:
Might support glycosylation reactions in the Golgi apparatus and, when released from cells, might catalyze the hydrolysis of extracellular nucleotides. Hydrolyzes preferentially nucleoside 5'-diphosphates, nucleoside 5'-triphosphates are hydrolyzed only to a minor extent, there is no hydrolysis of nucleoside 5'-monophosphates. The order of activity with different substrates is GDP > IDP >> UDP = CDP >> ADP (By similarity).
Gene Name:
ENTPD6
Uniprot ID:
O75354
Molecular weight:
51159.26
Reactions
IDP + Water → Inosinic acid + Phosphoric aciddetails
General function:
Involved in hydrolase activity
Specific function:
Uridine diphosphatase (UDPase) that promotes protein N-glycosylation and ATP level regulation. UDP hydrolysis promotes protein N-glycosylation and folding in the endoplasmic reticulum, as well as elevated ATP consumption in the cytosol via an ATP hydrolysis cycle. Together with CMPK1 and AK1, constitutes an ATP hydrolysis cycle that converts ATP to AMP and results in a compensatory increase in aerobic glycolysis. Also hydrolyzes GDP and IDP but not any other nucleoside di-, mono- or triphosphates, nor thiamine pyrophosphate. Plays a key role in the AKT1-PTEN signaling pathway by promoting glycolysis in proliferating cells in response to phosphoinositide 3-kinase (PI3K) signaling (By similarity).
Gene Name:
ENTPD5
Uniprot ID:
O75356
Molecular weight:
47516.985
Reactions
IDP + Water → Inosinic acid + Phosphoric aciddetails
General function:
Involved in ATP binding
Specific function:
Phosphorylates uridine and cytidine to uridine monophosphate and cytidine monophosphate. Does not phosphorylate deoxyribonucleosides or purine ribonucleosides. Can use ATP or GTP as a phosphate donor. Can also phosphorylate cytidine and uridine nucleoside analogs such as 6-azauridine, 5-fluorouridine, 4-thiouridine, 5-bromouridine, N(4)-acetylcytidine, N(4)-benzoylcytidine, 5-fluorocytidine, 2-thiocytidine, 5-methylcytidine, and N(4)-anisoylcytidine.
Gene Name:
UCK1
Uniprot ID:
Q9HA47
Molecular weight:
22760.43
Reactions
Inosine triphosphate + Cytidine → IDP + Cytidine monophosphatedetails
Inosine triphosphate + Uridine → IDP + Uridine 5'-monophosphatedetails
General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes preferentially nucleoside 5'-diphosphates, nucleoside 5'-triphosphates are hydrolyzed only to a minor extent. The order of activity with different substrates is UDP >> GDP = CDP = TDP, AMP, ADP, ATP and UMP are not substrates. Preferred substrates for isoform 2 are CTP, UDP, CDP, GTP and GDP, while isoform 1 utilizes UTP and TTP.
Gene Name:
ENTPD4
Uniprot ID:
Q9Y227
Molecular weight:
69419.915
Reactions
IDP + Water → Inosinic acid + Phosphoric aciddetails
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate. Probably has a role in normal hematopoiesis by inhibition of granulocyte differentiation and induction of apoptosis.
Gene Name:
NME3
Uniprot ID:
Q13232
Molecular weight:
19014.85
Reactions
Adenosine triphosphate + IDP → ADP + Inosine triphosphatedetails
General function:
Not Available
Specific function:
Does not seem to have NDK kinase activity. Confers protection from cell death by Bax and alters the cellular levels of several antioxidant enzymes including Gpx5. May play a role in spermiogenesis by increasing the ability of late-stage spermatids to eliminate reactive oxygen species (By similarity).
Gene Name:
NME5
Uniprot ID:
P56597
Molecular weight:
Not Available
Reactions
Adenosine triphosphate + IDP → ADP + Inosine triphosphatedetails
General function:
Involved in nucleoside diphosphate kinase activity
Specific function:
Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate.
Gene Name:
NME7
Uniprot ID:
Q9Y5B8
Molecular weight:
42491.365
Reactions
Adenosine triphosphate + IDP → ADP + Inosine triphosphatedetails
General function:
Involved in phosphoenolpyruvate carboxykinase activity
Specific function:
Catalyzes the conversion of oxaloacetate (OAA) to phosphoenolpyruvate (PEP), the rate-limiting step in the metabolic pathway that produces glucose from lactate and other precursors derived from the citric acid cycle (By similarity).
Gene Name:
PCK2
Uniprot ID:
Q16822
Molecular weight:
47563.34
Reactions
Inosine triphosphate + Oxalacetic acid → IDP + Phosphoenolpyruvic acid + Carbon dioxidedetails