Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120252
Identification
Name: dADP
Description:A 2'-deoxyribonucleoside 5'-diphosphate obtained by deprotonation of the diphosphate OH groups of 2'-deoxyadenosine 5'-diphosphate (dADP); major species at pH 7.3.
Structure
Thumb
Synonyms:
  • 2'-deoxyadenosine 5'-diphosphate(3−)
  • dADP
  • dADP trianion
  • deoxyadenosine diphosphate(3−)
Chemical Formula: C10H12N5O9P2
Average Molecular Weight: 408.18
Monoisotopic Molecular Weight: 411.03452
InChI Key: DAEAPNUQQAICNR-RRKCRQDMSA-K
InChI: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)/p-3/t5-,6+,7+/m0/s1
CAS number: 2793-06-8
IUPAC Name:2'-deoxy-5'-O-[(phosphonatooxy)phosphinato]adenosine
Traditional IUPAC Name: {[(2R,3S)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid
SMILES:C(C3(C(CC(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O))OP(OP([O-])([O-])=O)([O-])=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities 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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Nucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct Parent Purine 2'-deoxyribonucleoside diphosphates
Alternative Parents
Substituents
  • Purine 2'-deoxyribonucleoside diphosphate
  • 6-aminopurine
  • Organic pyrophosphate
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Primary aromatic amine
  • Pyrimidine
  • Alkyl phosphate
  • Imidolactam
  • Imidazole
  • Azole
  • Oxolane
  • Heteroaromatic compound
  • Secondary alcohol
  • Azacycle
  • Organoheterocyclic compound
  • Oxacycle
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Primary amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-3
Melting point: Not Available
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
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
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
References
References:
  • 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 ]
  • 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 ]
  • 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 ]
  • Chen SD, Kao CH, Poon SK: Radionuclide imaging in primary amyloidosis with liver involvement. Clin Nucl Med. 1998 Jun;23(6):374-6. [9619324 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • Zaka R, Williams CJ: Role of the progressive ankylosis gene in cartilage mineralization. Curr Opin Rheumatol. 2006 Mar;18(2):181-6. [16462526 ]
  • 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 ]
  • Ryan LM, Rosenthal AK: Metabolism of extracellular pyrophosphate. Curr Opin Rheumatol. 2003 May;15(3):311-4. [12707586 ]
  • 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 ]
  • 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 ]
Synthesis Reference: Nara, 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
External Links:
ResourceLink
METABOLIGHTSMTBLC57667
HMDBHMDB01508
BIGG34254
CHEMSPIDER19992628
CHEBI57667
PUBCHEM21125569
LIGAND-CPDC00206
CAS2793-06-8