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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:51 UTC
HMDB IDHMDB01508
Secondary Accession NumbersNone
Metabolite Identification
Common NamedADP
DescriptionDeoxyadenosine diphosphate has been identified in the mononuclear cells of a patient affected with in inherited adenosine deaminase deficiency (OMIM 102700 ) (PMID 6980023 ), and in in mononuclear cells of hemodialyzed patients. (PMID 11461945 ).
Structure
Thumb
Synonyms
ValueSource
2'-Deoxyadenosine-5'-diphosphateHMDB
Deoxyadenosine diphosphateHMDB
Chemical FormulaC10H15N5O9P2
Average Molecular Weight411.2017
Monoisotopic Molecular Weight411.034500127
IUPAC Name[({[(2R,3S)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
Traditional Name{[(2R,3S)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid
CAS Registry Number2793-06-8
SMILES
NC1=NC=NC2=C1N=CN2C1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(O)=O)O1
InChI Identifier
InChI=1S/C10H15N5O9P2/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(23-7)2-22-26(20,21)24-25(17,18)19/h3-7,16H,1-2H2,(H,20,21)(H2,11,12,13)(H2,17,18,19)/t5-,6+,7?/m0/s1
InChI KeyInChIKey=DAEAPNUQQAICNR-GFCOJPQKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside diphosphates. These are purine nucleotides with diphosphate 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 diphosphates
Alternative Parents
Substituents
  • Purine 2'-deoxyribonucleoside diphosphate
  • Organic pyrophosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
Biofunction
  • DNA component
ApplicationNot Available
Cellular locations
  • 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 Solubility2.8 mg/mLALOGPS
logP-1.6ALOGPS
logP-4.4ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
pKa (Strongest Basic)5.01ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area212.37 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity83.43 m3·mol-1ChemAxon
Polarizability33.53 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Mitochondria
  • Nucleus
Biofluid LocationsNot Available
Tissue Location
  • Cartilage
  • Epidermis
  • Fibroblasts
  • Neuron
  • Platelet
  • Skeletal Muscle
  • Spleen
Pathways
NameSMPDB LinkKEGG Link
Adenine phosphoribosyltransferase deficiency (APRT)SMP00535Not Available
Adenosine Deaminase DeficiencySMP00144Not Available
Adenylosuccinate Lyase DeficiencySMP00167Not Available
AICA-RibosiduriaSMP00168Not Available
Azathioprine PathwaySMP00427Not Available
Gout or Kelley-Seegmiller SyndromeSMP00365Not Available
Lesch-Nyhan Syndrome (LNS)SMP00364Not Available
Mercaptopurine PathwaySMP00428Not Available
Mitochondrial DNA depletion syndromeSMP00536Not Available
Molybdenum Cofactor DeficiencySMP00203Not Available
Myoadenylate deaminase deficiencySMP00537Not Available
Purine MetabolismSMP00050map00230
Purine Nucleoside Phosphorylase DeficiencySMP00210Not Available
Thioguanine PathwaySMP00430Not Available
Xanthine Dehydrogenase Deficiency (Xanthinuria)SMP00220Not Available
Xanthinuria type ISMP00512Not Available
Xanthinuria type IISMP00513Not Available
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 IDFDB022662
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00206
BioCyc IDDADP
BiGG ID34254
Wikipedia Linkdeoxyadenosine diphosphate
NuGOwiki LinkHMDB01508
Metagene LinkHMDB01508
METLIN ID6286
PubChem Compound53477733
PDB IDNot Available
ChEBI ID16174
References
Synthesis ReferenceNara, Takashi; Misawa, Masanaru. Bacterial phosphorylation of 5'-deoxyadenosine monophosphate to di- or triphosphate. Jpn. Tokkyo Koho (1971), 2 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Imbach T, Schenk B, Schollen E, Burda P, Stutz A, Grunewald S, Bailie NM, King MD, Jaeken J, Matthijs G, Berger EG, Aebi M, Hennet T: Deficiency of dolichol-phosphate-mannose synthase-1 causes congenital disorder of glycosylation type Ie. J Clin Invest. 2000 Jan;105(2):233-9. [10642602 ]
  2. Cartwright PH, Ilchyshyn A, Ilderton E, Yardley HJ: Modulation of phospholipase A2 activity in extracts of lesion-free psoriatic epidermis by alkaline phosphatase and a protein phosphatase inhibitor. Br J Dermatol. 1988 Mar;118(3):333-8. [2833303 ]
  3. Doherty M, Belcher C, Regan M, Jones A, Ledingham J: Association between synovial fluid levels of inorganic pyrophosphate and short term radiographic outcome of knee osteoarthritis. Ann Rheum Dis. 1996 Jul;55(7):432-6. [8774160 ]
  4. Chen SD, Kao CH, Poon SK: Radionuclide imaging in primary amyloidosis with liver involvement. Clin Nucl Med. 1998 Jun;23(6):374-6. [9619324 ]
  5. Yepes M, Moore E, Brown SA, Hanscom HN, Smith EP, Lawrence DA, Winkles JA: Progressive ankylosis (Ank) protein is expressed by neurons and Ank immunohistochemical reactivity is increased by limbic seizures. Lab Invest. 2003 Jul;83(7):1025-32. [12861042 ]
  6. Blackburn MR, Datta SK, Kellems RE: Adenosine deaminase-deficient mice generated using a two-stage genetic engineering strategy exhibit a combined immunodeficiency. J Biol Chem. 1998 Feb 27;273(9):5093-100. [9478961 ]
  7. Beltran J, Marty-Delfaut E, Bencardino J, Rosenberg ZS, Steiner G, Aparisi F, Padron M: Chondrocalcinosis of the hyaline cartilage of the knee: MRI manifestations. Skeletal Radiol. 1998 Jul;27(7):369-74. [9730327 ]
  8. Grubenmann CE, Frank CG, Kjaergaard S, Berger EG, Aebi M, Hennet T: ALG12 mannosyltransferase defect in congenital disorder of glycosylation type lg. Hum Mol Genet. 2002 Sep 15;11(19):2331-9. [12217961 ]
  9. Rother E, Brandl R, Baker DL, Goyal P, Gebhard H, Tigyi G, Siess W: Subtype-selective antagonists of lysophosphatidic Acid receptors inhibit platelet activation triggered by the lipid core of atherosclerotic plaques. Circulation. 2003 Aug 12;108(6):741-7. Epub 2003 Jul 28. [12885756 ]
  10. Collins ML, Eng S, Hoh R, Hellerstein MK: Measurement of mitochondrial DNA synthesis in vivo using a stable isotope-mass spectrometric technique. J Appl Physiol. 2003 Jun;94(6):2203-11. Epub 2003 Jan 31. [12562673 ]
  11. Cavusoglu Y, Entok E, Gorenek B, Kudaiberdieva G, Unalir A, Goktekin O, Birdane A, Ata N, Timuralp B: Reversible myoglobinuric renal failure following rhabdomyolysis as a rare complication of cardioversion. Pacing Clin Electrophysiol. 2003 Feb;26(2 Pt 1):645-6. [12710329 ]
  12. Zaka R, Williams CJ: Role of the progressive ankylosis gene in cartilage mineralization. Curr Opin Rheumatol. 2006 Mar;18(2):181-6. [16462526 ]
  13. Johnson K, Hashimoto S, Lotz M, Pritzker K, Goding J, Terkeltaub R: Up-regulated expression of the phosphodiesterase nucleotide pyrophosphatase family member PC-1 is a marker and pathogenic factor for knee meniscal cartilage matrix calcification. Arthritis Rheum. 2001 May;44(5):1071-81. [11352238 ]
  14. Ryan LM, Rosenthal AK: Metabolism of extracellular pyrophosphate. Curr Opin Rheumatol. 2003 May;15(3):311-4. [12707586 ]
  15. Simmonds HA, Webster DR, Perrett D, Reiter S, Levinsky RJ: Formation and degradation of deoxyadenosine nucleotides in inherited adenosine deaminase deficiency. Biosci Rep. 1982 May;2(5):303-14. [6980023 ]
  16. Sampol J, Dussol B, Fenouillet E, Capo C, Mege JL, Halimi G, Bechis G, Brunet P, Rochat H, Berland Y, Guieu R: High adenosine and deoxyadenosine concentrations in mononuclear cells of hemodialyzed patients. J Am Soc Nephrol. 2001 Aug;12(8):1721-8. [11461945 ]

Enzymes

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
Deoxyadenosine triphosphate + Cytidine → dADP + Cytidine monophosphatedetails
Deoxyadenosine triphosphate + Uridine → dADP + Uridine 5'-monophosphatedetails
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 + dADP → ADP + Deoxyadenosine triphosphatedetails
General function:
Involved in oxidation reduction
Specific function:
Provides the precursors necessary for DNA synthesis. Catalyzes the biosynthesis of deoxyribonucleotides from the corresponding ribonucleotides.
Gene Name:
RRM1
Uniprot ID:
P23921
Molecular weight:
90069.375
Reactions
dADP + Thioredoxin disulfide + Water → Thioredoxin + ADPdetails
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 + dADP → ADP + Deoxyadenosine 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 + dADP → ADP + Deoxyadenosine triphosphatedetails
General function:
Involved in oxidoreductase activity
Specific function:
Provides the precursors necessary for DNA synthesis. Catalyzes the biosynthesis of deoxyribonucleotides from the corresponding ribonucleotides. Inhibits Wnt signaling.
Gene Name:
RRM2
Uniprot ID:
P31350
Molecular weight:
44877.25
Reactions
dADP + Thioredoxin disulfide + Water → Thioredoxin + ADPdetails
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 + dADP → ADP + Deoxyadenosine 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. 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 + dADP → ADP + Deoxyadenosine 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. Inhibitor of p53-induced apoptosis.
Gene Name:
NME6
Uniprot ID:
O75414
Molecular weight:
22002.965
Reactions
Adenosine triphosphate + dADP → ADP + Deoxyadenosine 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:
HK3
Uniprot ID:
P52790
Molecular weight:
99024.56
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:
Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. Small ubiquitous enzyme involved in energy metabolism and nucleotide synthesis that is essential for maintenance and cell growth.
Gene Name:
AK1
Uniprot ID:
P00568
Molecular weight:
21634.725
Reactions
Adenosine triphosphate + Deoxyadenosine monophosphate → ADP + dADPdetails
General function:
Involved in ATP binding
Specific function:
Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. May also be active with GTP (By similarity).
Gene Name:
AK4
Uniprot ID:
P27144
Molecular weight:
25267.83
Reactions
Adenosine triphosphate + Deoxyadenosine monophosphate → ADP + dADPdetails
General function:
Involved in ATP binding
Specific function:
Adenylate kinase involved in maintaining ciliary structure and function (By similarity). Has highest activity toward AMP, and weaker activity toward dAMP, CMP and dCMP.
Gene Name:
AK7
Uniprot ID:
Q96M32
Molecular weight:
82657.68
Reactions
Adenosine triphosphate + Deoxyadenosine monophosphate → ADP + dADPdetails
General function:
Involved in ATP binding
Specific function:
Active on AMP and dAMP with ATP as a donor. When GTP is used as phosphate donor, the enzyme phosphorylates AMP, CMP, and to a small extent dCMP.
Gene Name:
AK5
Uniprot ID:
Q9Y6K8
Molecular weight:
60313.985
Reactions
Adenosine triphosphate + Deoxyadenosine monophosphate → ADP + dADPdetails
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
Reactions
Deoxyadenosine triphosphate + Pyruvic acid → dADP + Phosphoenolpyruvic aciddetails
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
Reactions
Deoxyadenosine triphosphate + Pyruvic acid → dADP + Phosphoenolpyruvic 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:
UCK2
Uniprot ID:
Q9BZX2
Molecular weight:
29298.92
Reactions
Deoxyadenosine triphosphate + Cytidine → dADP + Cytidine monophosphatedetails
Deoxyadenosine triphosphate + Uridine → dADP + Uridine 5'-monophosphatedetails
General function:
Involved in ATP binding
Specific function:
Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. This small ubiquitous enzyme involved in energy metabolism and nucleotide synthesis that is essential for maintenance and cell growth. Plays a key role in hematopoiesis.
Gene Name:
AK2
Uniprot ID:
P54819
Molecular weight:
24648.125
Reactions
Adenosine triphosphate + Deoxyadenosine monophosphate → ADP + dADPdetails
General function:
Involved in oxidoreductase activity
Specific function:
Plays a pivotal role in cell survival by repairing damaged DNA in a p53/TP53-dependent manner. Supplies deoxyribonucleotides for DNA repair in cells arrested at G1 or G2. Contains an iron-tyrosyl free radical center required for catalysis. Forms an active ribonucleotide reductase (RNR) complex with RRM1 which is expressed both in resting and proliferating cells in response to DNA damage.
Gene Name:
RRM2B
Uniprot ID:
Q7LG56
Molecular weight:
48786.6
Reactions
dADP + Thioredoxin disulfide + Water → Thioredoxin + ADPdetails
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
Deoxyadenosine triphosphate + Cytidine → dADP + Cytidine monophosphatedetails
Deoxyadenosine triphosphate + Uridine → dADP + Uridine 5'-monophosphatedetails
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 + dADP → ADP + Deoxyadenosine triphosphatedetails