P. aeruginosa Metabolome Database: ADP (PAMDB110479)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB110479

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

🔍MOL SDF PDB SMILES InChI View 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 Description

This 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 Class

Organic compounds

Class

Nucleosides, nucleotides, and analogues

Sub Class

Purine 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

purine ribonucleoside 5'-diphosphate (CHEBI:16761 )
adenosine 5'-phosphate (CHEBI:16761 )
Ribonucleotides (C00008 )

Physical Properties

State:

Solid

Charge:

-3

Melting point:

Not Available

Experimental Properties:

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	3.27 mg/mL	ALOGPS
logP	-1.6	ALOGPS
logP	-5.3	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.77	ChemAxon
pKa (Strongest Basic)	4.99	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	232.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	84.94 m³·mol^-1	ChemAxon
Polarizability	34.24 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Not Available

Reactions:

2'-deoxyribose + ATP → DEOXY-RIBOSE-5P + ADP + Hydrogen ion
ATP + dAMP → ADP + dADP
coenzyme A + acetate + ATP → phosphate + acetyl-CoA + ADP
pseudouridine + ATP → Hydrogen ion + pseudouridine 5'-phosphate + ADP
ATP + acetyl-CoA + Water → malonyl-CoA + ADP + phosphate + Hydrogen ion
dGMP + ATP → dGDP + ADP
ATP + DNA-N + Water → ADP + phosphate
ATP + protoporphyrin IX + MG+2 + Water → Hydrogen ion + Mg-protoporphyrin + phosphate + ADP
ATP + dIDP → ADP + dITP
beta-Alanine + (R)-pantoate + ATP → Hydrogen ion + (R)-pantothenate + phosphate + ADP
Deoxyadenosine + ATP → Hydrogen ion + dAMP + ADP
dADP + Water → ADP
UDP-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-L-lysine + D-Alanyl-D-alanine + ATP → Hydrogen ion + UDP-N-acetyl-α-D-muramoyl-L-alanyl-γ-D-glutamyl-L-lysyl-D-alanyl-D-alanine + phosphate + ADP
2-dehydro-3-deoxy-D-gluconate + ATP → Hydrogen ion + 2-dehydro-3-deoxy-D-gluconate 6-phosphate + ADP
ATP + dCMP → ADP + dCDP
Deoxyguanosine + ATP → Hydrogen ion + dGMP + ADP
Protein-L-serine-or-L-threonine + ATP → Protein-Ser-or-Thr-phosphate + ADP + Hydrogen ion
ATP + 4-Amino-5-hydroxymethyl-2-methylpyrimidine → Hydrogen ion + ADP + 4-Amino-2-methyl-5-phosphomethylpyrimidine
Glucopyranose + ATP → D-glucopyranose-6-phosphate + ADP + Hydrogen ion
chlorophyllide a + ADP + phosphate → protochlorophyllide a + ATP + Water

More...

Pathways:

Alanine Metabolism pae00250
Amino Sugar Metabolism pae00520
Ammonia Recycling pae00910
Arginine and Proline Metabolism pae00330
Beta Oxidation of Very Long Chain Fatty Acids pae01040
Bile Acid Biosynthesis pae00120
Citric Acid Cycle pae00020
Cysteine Metabolism pae00270
Folate Metabolism pae00670
Fructose and Mannose Degradation pae00051
Galactose Metabolism pae00052
Gluconeogenesis pae00010
Glutamate Metabolism pae00250
Glutathione Metabolism pae00480
Glycerolipid Metabolism pae00561
Glycine and Serine Metabolism pae00260
Glycolysis pae00010
Histidine Metabolism pae00340
Inositol Metabolism pae00562
Inositol Phosphate Metabolism pae00562
Mitochondrial Electron Transport Chain pae00190
Nicotinate and Nicotinamide Metabolism pae00760
Nucleotide Sugars Metabolism pae00520
Pantothenate and CoA Biosynthesis pae00770
Pentose Phosphate Pathway pae00030
Phosphatidylinositol Phosphate Metabolism pae00562
Propanoate Metabolism pae00640
Purine Metabolism pae00230
Pyrimidine Metabolism pae00240
Pyruvate Metabolism pae00620
Riboflavin Metabolism pae00740
Selenoamino Acid Metabolism pae00450
Sphingolipid Metabolism pae00500
Starch and Sucrose Metabolism pae00500
Steroid Biosynthesis pae00100
Sulfate/Sulfite Metabolism pae00920
Thiamine Metabolism pae00730
Urea Cycle pae00330
Valine, Leucine and Isoleucine Degradation pae00280

Spectra

Spectra:

Spectrum Type	Description	Splash Key
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-0301900000-f65eba52a00479514d8e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-0900000000-cdad0c415295c75e0b67	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-1900000000-1f27fdf6dbd77cbe927d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0102981000-79c6771fae3255f75825	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0209000000-24c7ad0d0646786963be	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0009000000-d266bbe08f0bcb8102b4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0000090000-8a788ef5a2c7ccc534e1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-004i-6900600000-fe2194fd2a27df917e5b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available
1D NMR	1H NMR Spectrum	Not Available
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not 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)

Links

External Links:

Resource	Link
CAS	58-64-0
ChEBI	456216
ChemSpider	5414423
HMDB	HMDB01341
IAF1260	33496
KEGG	C00008
MetaboLights	MTBLC456216
PubChem	7058055

ADP (PAMDB110479)

Structure for ADP (PAMDB110479)