ADP (PAMDB110479)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110479
Identification
Name: ADP
Description:An organophosphate oxoanion that is the trianion of adenosine 5'-diphosphate arising from deprotonation of all three OH groups of the diphosphate; major species present at pH 7.3.
Structure
Thumb
๐Ÿ”MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • adenosine pyrophosphate
  • adenosine 5'-pyrophosphate
  • adenosine-5'-diphosphate
  • adenosine-diphosphate
  • adenosine-5-diphosphate
Chemical Formula: C10H12N5O10P2
Average Molecular Weight: 424.18
Monoisotopic Molecular Weight: 427.0294147485
InChI Key: XTWYTFMLZFPYCI-KQYNXXCUSA-K
InChI: InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/p-3/t4-,6-,7-,10-/m1/s1
CAS number: 58-64-0
IUPAC Name:adenosine 5'-diphosphate
Traditional IUPAC Name: adenosine-diphosphate
SMILES:C(C3(C(C(C(N2(C1(=C(C(=NC=N1)N)N=C2)))O3)O)O))OP(OP(=O)([O-])[O-])([O-])=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Nucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct Parent Purine ribonucleoside diphosphates
Alternative Parents
Substituents
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Monosaccharide
  • Pyrimidine
  • Imidolactam
  • N-substituted imidazole
  • Primary aromatic amine
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Imidazole
  • Azole
  • Oxolane
  • Heteroaromatic compound
  • 1,2-diol
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Alcohol
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
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 Solubility3.27 mg/mLALOGPS
logP-1.6ALOGPS
logP-5.3ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
pKa (Strongest Basic)4.99ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area232.6 ร…2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity84.94 m3ยทmol-1ChemAxon
Polarizability34.24 ร…3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
2'-deoxyribose + ATP โ†’ DEOXY-RIBOSE-5P + ADP + Hydrogen ion
ATP + dAMP โ†’ ADP + dADP
coenzyme A + acetate + ATP โ†’ phosphate + acetyl-CoA + ADP
pseudouridine + ATP โ†’ Hydrogen ion + pseudouridine 5'-phosphate + ADP
ATP + acetyl-CoA + Water โ†’ malonyl-CoA + ADP + phosphate + Hydrogen ion
dGMP + ATP โ†’ dGDP + ADP
ATP + DNA-N + Water โ†’ ADP + phosphate
ATP + protoporphyrin IX + MG+2 + Water โ†’ Hydrogen ion + Mg-protoporphyrin + phosphate + ADP
ATP + dIDP โ†’ ADP + dITP
beta-Alanine + (R)-pantoate + ATP โ†’ Hydrogen ion + (R)-pantothenate + phosphate + ADP
Deoxyadenosine + ATP โ†’ Hydrogen ion + dAMP + ADP
dADP + Water โ†’ ADP
UDP-N-acetylmuramoyl-L-alanyl-ฮณ-D-glutamyl-L-lysine + D-Alanyl-D-alanine + ATP โ†’ Hydrogen ion + UDP-N-acetyl-ฮฑ-D-muramoyl-L-alanyl-ฮณ-D-glutamyl-L-lysyl-D-alanyl-D-alanine + phosphate + ADP
2-dehydro-3-deoxy-D-gluconate + ATP โ†’ Hydrogen ion + 2-dehydro-3-deoxy-D-gluconate 6-phosphate + ADP
ATP + dCMP โ†’ ADP + dCDP
Deoxyguanosine + ATP โ†’ Hydrogen ion + dGMP + ADP
Protein-L-serine-or-L-threonine + ATP โ†’ Protein-Ser-or-Thr-phosphate + ADP + Hydrogen ion
ATP + 4-Amino-5-hydroxymethyl-2-methylpyrimidine โ†’ Hydrogen ion + ADP + 4-Amino-2-methyl-5-phosphomethylpyrimidine
Glucopyranose + ATP โ†’ D-glucopyranose-6-phosphate + ADP + Hydrogen ion
chlorophyllide a + ADP + phosphate โ†’ protochlorophyllide a + ATP + Water
METHYLENE-THF-GLU-N + L-glutamate + ATP โ†’ METHYLENE-THF-GLU-N + ADP + phosphate
alpha-D-Glucose + ATP โ†’ Hydrogen ion + ฮฑ-D-glucose 6-phosphate + ADP
5-oxoproline + Water + ATP โ†’ Hydrogen ion + L-glutamate + phosphate + ADP
Hydrogen ion + ATP + Water โ†’ Hydrogen ion + ADP + phosphate
alpha-N-Peptidyl-LGlutamate + L-glutamate + ATP โ†’ CPD0-2471 + ADP + phosphate + Hydrogen ion
thiamin + ATP โ†’ Hydrogen ion + thiamin phosphate + ADP
ฮฑ-D-Kdo-(2โ†’4)-ฮฑ-D-Kdo-(2โ†’6)-lipid A + ADP-L-glycero-beta-D-manno-heptose โ†’ heptosyl-Kdo2-lipid A + ADP + Hydrogen ion
ALGINATE + Water + ATP โ†’ ALGINATE + phosphate + ADP + Hydrogen ion
dADP + ATP โ†’ dATP + ADP
LysW-L-glutamate + ATP โ†’ LysW-L-glutamate-5-phosphate + ADP
dGDP + ATP โ†’ dGTP + ADP
ฮฑ-Kdo-(2->4)-ฮฑ-Kdo-(2->6)-lipid IVA + ADP-L-glycero-beta-D-manno-heptose โ†’ Hydrogen ion + heptosyl-Kdo2-lipid IVA + ADP
D-ALPHABETA-D-HEPTOSE-7-PHOSPHATE + ATP โ†’ Hydrogen ion + D-glycero-ฮฒ-D-manno-heptose 1,7-bisphosphate + ADP
1,6-anhydro-N-acetyl-ฮฒ-muramate + ATP + Water โ†’ Hydrogen ion + N-acetyl-ฮฒ-muramate 6-phosphate + ADP
ATP โ†’ ADP
cob(II)yrinate c-monoamide + L-Glutamine + ATP + Water โ†’ cob(II)yrinate a,c-diamide + L-glutamate + ADP + phosphate + Hydrogen ion
ATP + acetyl-CoA + Hydrogen carbonate โ†’ Hydrogen ion + malonyl-CoA + phosphate + ADP
cobyrinate + L-Glutamine + ATP + Water โ†’ cob(II)yrinate c-monoamide + L-glutamate + ADP + phosphate + Hydrogen ion
ATP โ†’ ADP + phosphate
Water + ATP โ†’ Hydrogen ion + phosphate + ADP
cobyrinate + L-Glutamine + ATP + Water โ†’ cob(II)yrinate a,c-diamide + L-glutamate + ADP + phosphate + Hydrogen ion
Nucleoside-Diphosphates + ATP โ†’ Nucleoside-Triphosphates + ADP
L-Glutamine + ATP + Water โ†’ L-glutamate + phosphate + ADP + Hydrogen ion
Xenobiotic + Water + ATP โ†’ Xenobiotic + phosphate + ADP
GDP + ADP โ†’ GTP + AMP
galactosyl-(glucosyl)3-(heptosyl)3-Kdo2-lipid A-bisphosphate + ADP-L-glycero-beta-D-manno-heptose โ†’ Hydrogen ion + lipid A-core + ADP
UDP-N-acetyl-ฮฑ-D-muramate + L-alanyl-ฮณ-D-glutamyl-meso-diaminopimelate + ATP โ†’ Hydrogen ion + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate + ADP + phosphate
L-glutamate + LysW-C-Terminal-L-Glutamate + ATP โ†’ LysW-L-glutamate + ADP + phosphate + Hydrogen ion
cis-geranyl-CoA + Hydrogen carbonate + ATP โ†’ 3-(4-methylpent-3-en-1-yl)-pent-2-enedioyl-CoA + phosphate + ADP + Hydrogen ion
NAD+ + ATP โ†’ Hydrogen ion + NADP+ + ADP
glucosyl-(heptosyl)3-Kdo2-lipid A-phosphate + ATP โ†’ Hydrogen ion + glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate + ADP
ATP + Water + K+ โ†’ ADP + phosphate + K+ + Hydrogen ion
glucosyl-(heptosyl)2-Kdo2-lipid A-phosphate + ADP-L-glycero-beta-D-manno-heptose โ†’ Hydrogen ion + glucosyl-(heptosyl)3-Kdo2-lipid A-phosphate + ADP
ฮฒ-D-fructofuranose 6-phosphate + ADP โ†’ Hydrogen ion + fructose 1,6-bisphosphate + AMP
glucosyl-(heptosyl)2-Kdo2-lipid A + ATP โ†’ Hydrogen ion + glucosyl-(heptosyl)2-Kdo2-lipid A-phosphate + ADP
ATP + IDP โ†’ ITP + ADP
L-1-PHOSPHATIDYL-GLYCEROL + ATP โ†’ L-1-PHOSPHATIDYL-GLYCEROL-P + ADP + Hydrogen ion
heptosyl-Kdo2-lipid A + ADP-L-glycero-beta-D-manno-heptose โ†’ Hydrogen ion + (heptosyl)2-Kdo2-lipid A + ADP
ATP + 4-methyl-5-(ฮฒ-hydroxyethyl)thiazole โ†’ Hydrogen ion + ADP + 4-methyl-5-(2-phosphonooxyethyl)thiazole
More...

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0301900000-f65eba52a00479514d8eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-0900000000-cdad0c415295c75e0b67View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-1900000000-1f27fdf6dbd77cbe927dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0102981000-79c6771fae3255f75825View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0209000000-24c7ad0d0646786963beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0009000000-d266bbe08f0bcb8102b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0000090000-8a788ef5a2c7ccc534e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-004i-6900600000-fe2194fd2a27df917e5bView in MoNA
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
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18. [15882454 ]
  • Cuisset T, Frere C, Quilici J, Barbou F, Morange PE, Hovasse T, Bonnet JL, Alessi MC: High post-treatment platelet reactivity identified low-responders to dual antiplatelet therapy at increased risk of recurrent cardiovascular events after stenting for acute coronary syndrome. J Thromb Haemost. 2006 Mar;4(3):542-9. Epub 2005 Dec 22. [16371119 ]
  • Quinton TM, Kim S, Jin J, Kunapuli SP: Lipid rafts are required in Galpha(i) signaling downstream of the P2Y12 receptor during ADP-mediated platelet activation. J Thromb Haemost. 2005 May;3(5):1036-41. [15869601 ]
  • Saxena R, Gupta M, Gupta S, Kannan M, Ahmed RP, Choudhry VP: Inherited heterogenous defect in platelet aggregation selectively with ADP and epinephrine--a series of 25 cases. Indian J Pathol Microbiol. 2005 Jul;48(3):345-8. [16761747 ]
  • Corsonello A, Malara A, De Domenico D, Damiano MC, Mirone S, Loddo S, Ientile R, Corica F: Effects of magnesium sulphate on leptin-dependent platelet aggregation: an ex vivo study. Magnes Res. 2005 Mar;18(1):7-11. [15945611 ]
  • Imura Y, Stassen JM, Bunting S, Stockmans F, Collen D: Antithrombotic properties of L-cysteine, N-(mercaptoacetyl)-D-Tyr-Arg-Gly-Asp-sulfoxide (G4120) in a hamster platelet-rich femoral vein thrombosis model. Blood. 1992 Sep 1;80(5):1247-53. [1515641 ]
  • Cuisset T, Frere C, Quilici J, Morange PE, Nait-Saidi L, Carvajal J, Lehmann A, Lambert M, Bonnet JL, Alessi MC: Benefit of a 600-mg loading dose of clopidogrel on platelet reactivity and clinical outcomes in patients with non-ST-segment elevation acute coronary syndrome undergoing coronary stenting. J Am Coll Cardiol. 2006 Oct 3;48(7):1339-45. Epub 2006 Sep 12. [17010792 ]
  • Vigue C, Vigue L, Huszar G: Adenosine triphosphate (ATP) concentrations and ATP/adenosine diphosphate ratios in human sperm of normospermic, oligospermic, and asthenospermic specimens and in their swim-up fractions: lack of correlation between ATP parameters and sperm creatine kinase concentrations. J Androl. 1992 Jul-Aug;13(4):305-11. [1399831 ]
  • Smith SM, Judge HM, Peters G, Storey RF: Multiple antiplatelet effects of clopidogrel are not modulated by statin type in patients undergoing percutaneous coronary intervention. Platelets. 2004 Dec;15(8):465-74. [15763887 ]
  • Ji Q, Ghaly M, Hjemdahl P, Tornvall P, Li N: Contrast medium attenuates platelet activation and platelet-leukocyte cross-talk. Thromb Haemost. 2005 May;93(5):922-6. [15886810 ]
  • Morshedi M, Oehninger S, Blackmore P, Bocca S, Coddington C, Hodgen G: Investigation of some biochemical and functional effects of cryopreservation of human spermatozoa using an automated freezing-quick-thawing method. Int J Androl. 1995 Dec;18(6):279-86. [8719843 ]
  • Hua J, Suguro S, Iwabuchi K, Tsutsumi-Ishii Y, Sakamoto K, Nagaoka I: Glucosamine, a naturally occurring amino monosaccharide, suppresses the ADP-mediated platelet activation in humans. Inflamm Res. 2004 Dec;53(12):680-8. [15654516 ]
  • Shabanova EY, Mindukshev IV, Malakhovskaya EA, Vivulanets EV, Petrishchev NN, Krivchenko AI: Cooperative type of platelet hypersensitivity to ADP. Bull Exp Biol Med. 2005 Sep;140(3):282-4. [16307036 ]
Synthesis Reference: Yamagata, Yukio. Prebiotic formation of ADP and ATP from AMP, calcium phosphates and cyanate in aqueous solution. Origins of Life and Evolution of the Biosphere (1999), 29(5), 511-520.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CAS58-64-0
ChEBI456216
ChemSpider5414423
HMDBHMDB01341
IAF126033496
KEGGC00008
MetaboLightsMTBLC456216
PubChem7058055