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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-06-19 22:08:11 UTC
HMDB IDHMDB0000058
Secondary Accession Numbers
  • HMDB00058
Metabolite Identification
Common NameCyclic AMP
DescriptionCyclic AMP is an adenine nucleotide containing one phosphate group which is esterified to both the 3'- and 5'-positions of the sugar moiety. It is a second messenger and a key intracellular regulator, functioning as a mediator of activity for a number of hormones, including epinephrine, glucagon, and ACTH. cAMP is synthesized from ATP by adenylate cyclase. Adenylate cyclase is located at the cell membranes. Adenylate cyclase is activated by the hormones glucagon and adrenaline and by G protein. Liver adenylate cyclase responds more strongly to glucagon, and muscle adenylate cyclase responds more strongly to adrenaline. cAMP decomposition into AMP is catalyzed by the enzyme phosphodiesterase.
Structure
Thumb
Synonyms
ValueSource
Adenosine 3',5'-cyclic monophosphateChEBI
Adenosine 3',5'-cyclic phosphateChEBI
Adenosine 3',5'-phosphateChEBI
ADENOSINE-3',5'-cyclic-monophosphATEChEBI
CAMPChEBI
Cyclic adenylic acidChEBI
Adenosine 3',5'-cyclic monophosphoric acidGenerator
Adenosine 3',5'-cyclic phosphoric acidGenerator
Adenosine 3',5'-phosphoric acidGenerator
ADENOSINE-3',5'-cyclic-monophosphoric acidGenerator
Cyclic adenylateGenerator
3'5'-Cyclic AMPHMDB
6-(6-amino-9H-Purin-9-yl)tetrahydro-4H-furo[3,2-D][1,3,2]dioxaphosphinine-2,7-diol 2-oxideHMDB
AcrasinHMDB
Adenosine 3',5'-cyclophosphateHMDB
Adenosine 3',5'-monophosphateHMDB
Adenosine 3,5'-cyclic monophosphorateHMDB
Adenosine 3,5'-cyclic monophosphoric acidHMDB
Adenosine cyclic monophosphateHMDB
Adenosine cyclic-monophosphateHMDB
Adenosine-cyclic-phosphateHMDB
Adenosine-cyclic-phosphoric-acidHMDB
Cyclic 3',5'-adenylateHMDB
Cyclic 3',5'-adenylic acidHMDB
Cyclic 3',5'-AMPHMDB
Cyclic adenosine 3',5'-phosphateHMDB
3',5'-Monophosphate, adenosine cyclicMeSH
Cyclic AMP, disodium saltMeSH
Cyclic AMP, monopotassium saltMeSH
Cyclic AMP, sodium saltMeSH
AMP, CyclicMeSH
Adenosine cyclic 3',5' monophosphateMeSH
Adenosine cyclic-3',5'-monophosphateMeSH
Cyclic AMP, (R)-isomerMeSH
Cyclic AMP, monosodium saltMeSH
Adenosine cyclic 3',5'-monophosphateMeSH
Monophosphate, adenosine cyclicMeSH
Adenosine cyclic 3,5 monophosphateMeSH
Cyclic 3',5'-monophosphate, adenosineMeSH
Cyclic AMP, monoammonium saltMeSH
Cyclic monophosphate, adenosineMeSH
Cyclic-3',5'-monophosphate, adenosineMeSH
Chemical FormulaC10H12N5O6P
Average Molecular Weight329.2059
Monoisotopic Molecular Weight329.052519653
IUPAC Name(4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-2-one
Traditional Namecyclic adenosine monophosphate
CAS Registry Number60-92-4
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(O)(=O)O[C@H]2[C@H]1O
InChI Identifier
InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
InChI KeyIVOMOUWHDPKRLL-KQYNXXCUSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 3',5'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C3 and C5 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassCyclic purine nucleotides
Direct Parent3',5'-cyclic purine nucleotides
Alternative Parents
Substituents
  • 3',5'-cyclic purine ribonucleotide
  • Pentose phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Purine
  • Imidazopyrimidine
  • Aminopyrimidine
  • Organic phosphoric acid derivative
  • N-substituted imidazole
  • Monosaccharide
  • Pyrimidine
  • Imidolactam
  • Imidazole
  • Azole
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point219 - 220 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4 mg/mLNot Available
LogP-2.96HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility3.58 g/LALOGPS
logP-2.3ALOGPS
logP-3.8ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.83ChemAxon
pKa (Strongest Basic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area154.84 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity70.29 m³·mol⁻¹ChemAxon
Polarizability28.22 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9761000000-ed8f1fea0ef2e7b43ff8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-03du-2971000000-c0200940e0e88308fbdeView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9761000000-ed8f1fea0ef2e7b43ff8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-03du-2971000000-c0200940e0e88308fbdeView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fbl-3901000000-b95501fad426dc61082fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03y0-3922000000-7e84eb99b8248254daa6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0009000000-02ee7f342f5c1bada389View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-0009000000-a00a2165c3d37c4e1ef2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-0109000000-7f48145f84828c2bbd5dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0119000000-d94a34a13521ae3d4692View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-f10e1d70e30865424af6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03dr-0629000000-bf4ec1094b7991c3633cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03dr-0629000000-9736faaf70ec79d5bd03View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0109000000-6bf3784f4b710ce04a3eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03dr-0629000000-3f5ea9ba1508e359ad80View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03dr-0519000000-059e8569ee179529bf21View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0009000000-88dad10a362b1088849eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0509004000-bb02289fcd39ac1a203cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-1900000000-da49323734f24bf724d6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-a4e60131f41413b6fecfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0009000000-98ee4e70689c06adc603View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-056r-0409005001-97fd793d1d14a84c3530View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0900000000-1f2045ac2ff736aa80a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-8bbb24702fa6ccd76268View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0009000000-6d23df7535894180e6dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-001i-0009000000-c527aad341e122fc9beaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-001i-0209000000-1bb2d660cc00c85a808fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-003r-2904000000-865c1b989665f73ac3f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0904000000-f37dad1d4334840eb74eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-8b2624b0c421f5f77e8eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-3052962b6de42b1e2f5dView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Golgi apparatus
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0085 +/- 0.0005 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.020 +/- 0.004 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.020+/- 0.004 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.024 (0.022-0.026) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.021 +/- 0.008 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.020 (0.016-0.024) uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.38 +/- 0.14 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.22 +/- 0.055 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0077 +/- 0.0003 uMAdult (>18 years old)MaleSildenafil-induced headache details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0110 +/- 0.0028 uMAdult (>18 years old)BothIdiopathic polyneuritis details
Cerebrospinal Fluid (CSF)Detected and Quantified0.033 +/- 0.012 uMAdult (>18 years old)Not Specified
Meningitis
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00860 (0.00620-0.0110) uMAdult (>18 years old)Both
Hypoxic-ischemic encephalopathy
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.014 (0.012-0.017) uMAdult (>18 years old)Both
Hypoxic-ischemic encephalopathy
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0202 +/- 0.004 uMAdult (>18 years old)Not SpecifiedInitial slight suspicion of meningitis with normal CSF details
Cerebrospinal Fluid (CSF)Detected and Quantified0.034 (0.021-0.046) uMAdult (>18 years old)Both
Meningitis
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.011 (0.0082-0.014) uMAdult (>18 years old)BothIdiopathic polyneuritis details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedUnclassified IBD details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedCrohns disease details
UrineDetected and Quantified0.24 +/- 0.028 umol/mmol creatinineAdult (>18 years old)BothChronic renal failure details
Associated Disorders and Diseases
Disease References
Chronic renal failure
  1. Dimitrakov D, Kumchev E, Lyutakova E, Ledzhev I, Nikolov D, Tsekov V: Cyclic adenosine monophosphate (cAMP) levels in predialysis patients with chronic renal failure. Folia Med (Plovdiv). 1997;39(1):29-33. [PubMed:9141788 ]
Crohn's disease
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Hypoxic-ischemic encephalopathy
  1. Liu H, Chang L, Chen Y, Xia S, Zhang X: Clinical implication of the changes of cAMP, TXA2 and PGI2 in CSF of asphyxiated newborns. J Huazhong Univ Sci Technolog Med Sci. 2003;23(2):195-7, 200. [PubMed:12973949 ]
Idiopathic polyneuritis
  1. Lerche A, Svenson M, Wiik A: Cerebrospinal fluid levels of cyclic nucleotides in meningitis and idiopathic polyneuritis. Acta Neurol Scand. 1984 Mar;69(3):168-75. [PubMed:6326460 ]
Meningitis
  1. Lerche A, Svenson M, Wiik A: Cerebrospinal fluid levels of cyclic nucleotides in meningitis and idiopathic polyneuritis. Acta Neurol Scand. 1984 Mar;69(3):168-75. [PubMed:6326460 ]
Headache
  1. Kruuse C, Frandsen E, Schifter S, Thomsen LL, Birk S, Olesen J: Plasma levels of cAMP, cGMP and CGRP in sildenafil-induced headache. Cephalalgia. 2004 Jul;24(7):547-53. [PubMed:15196297 ]
Ulcerative colitis
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001497
KNApSAcK IDC00001497
Chemspider ID5851
KEGG Compound IDC00575
BioCyc IDCAMP
BiGG ID1484809
Wikipedia LinkCyclic_AMP
METLIN ID5120
PubChem Compound6076
PDB IDCMP
ChEBI ID17489
References
Synthesis ReferenceGenieser, H. G.; Butt, E.; Bottin, U.; Dostmann, W.; Jastorff, B. Synthesis of the 3',5'-cyclic phosphates from unprotected nucleosides. Synthesis (1989), (1), 53-4.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Imashuku S, Todo S, Nakajima F: [Intra-aortic prostaglandin E1 infusion in the treatment of advanced neuroblastoma]. Gan To Kagaku Ryoho. 1983 Sep;10(9):1936-43. [PubMed:6311112 ]
  2. Wine JJ, Joo NS: Submucosal glands and airway defense. Proc Am Thorac Soc. 2004;1(1):47-53. [PubMed:16113412 ]
  3. Onali P, Strada SJ, Chang L, Epstein PM, Hersh EM, Thompson WJ: Purification and characterization of high-affinity cyclic adenosine 5'-monophosphate phosphodiesterases from human acute myelogenous leukemic cells. Cancer Res. 1985 Mar;45(3):1384-91. [PubMed:2982489 ]
  4. Rademaker MT, Charles CJ, Lewis LK, Yandle TG, Cooper GJ, Coy DH, Richards AM, Nicholls MG: Beneficial hemodynamic and renal effects of adrenomedullin in an ovine model of heart failure. Circulation. 1997 Sep 16;96(6):1983-90. [PubMed:9323090 ]
  5. Mashayekhi F, Aghahoseini F, Rezaie A, Zamani MJ, Khorasani R, Abdollahi M: Alteration of cyclic nucleotides levels and oxidative stress in saliva of human subjects with periodontitis. J Contemp Dent Pract. 2005 Nov 15;6(4):46-53. [PubMed:16299606 ]
  6. Sugo T, Tachimoto H, Chikatsu T, Murakami Y, Kikukawa Y, Sato S, Kikuchi K, Nagi T, Harada M, Ogi K, Ebisawa M, Mori M: Identification of a lysophosphatidylserine receptor on mast cells. Biochem Biophys Res Commun. 2006 Mar 24;341(4):1078-87. Epub 2006 Jan 25. [PubMed:16460680 ]
  7. Watanabe K, Beinborn M, Nagamatsu S, Ishida H, Takahashi S: Menetrier's disease in a patient with Helicobacter pylori infection is linked to elevated glucagon-like peptide-2 activity. Scand J Gastroenterol. 2005 Apr;40(4):477-81. [PubMed:16028444 ]
  8. Naef A, Keller HU: A short transient increase in cyclic adenosine 3', 5'-monophosphate levels of neutrophil granulocytes following exposure to chemotactic factors. Adv Exp Med Biol. 1982;141:39-48. [PubMed:6283833 ]
  9. Kukreja SC, Shevrin DH, Wimbiscus SA, Ebeling PR, Danks JA, Rodda CP, Wood WI, Martin TJ: Antibodies to parathyroid hormone-related protein lower serum calcium in athymic mouse models of malignancy-associated hypercalcemia due to human tumors. J Clin Invest. 1988 Nov;82(5):1798-802. [PubMed:2846659 ]
  10. Wickenheisser JK, Nelson-DeGrave VL, McAllister JM: Human ovarian theca cells in culture. Trends Endocrinol Metab. 2006 Mar;17(2):65-71. Epub 2006 Feb 7. [PubMed:16460956 ]
  11. Fouassier L, Chinet T, Robert B, Carayon A, Balladur P, Mergey M, Paul A, Poupon R, Capeau J, Barbu V, Housset C: Endothelin-1 is synthesized and inhibits cyclic adenosine monophosphate- dependent anion secretion by an autocrine/paracrine mechanism in gallbladder epithelial cells. J Clin Invest. 1998 Jun 15;101(12):2881-8. [PubMed:9637723 ]
  12. Carceles MD, Ribo AR, Davalos R, Martinez T, Hernandez J: Effect of diazepam on adenosine 3',5'-cyclic monophosphate (cAMP) plasma levels in anesthetized patients. Clin Ther. 2004 May;26(5):737-43. [PubMed:15220017 ]
  13. Chu MS, Chang CF, Yang CC, Bau YC, Ho LL, Hung SC: Signalling pathway in the induction of neurite outgrowth in human mesenchymal stem cells. Cell Signal. 2006 Apr;18(4):519-30. Epub 2005 Aug 11. [PubMed:16098715 ]
  14. Rudman D, O'Brien MS, McKinney AS, Hoffman JC Jr, Patterson JH: Observations on the cyclic nucleotide concentrations in human cerebrospinal fluid. J Clin Endocrinol Metab. 1976 Jun;42(6):1088-97. [PubMed:180045 ]
  15. Machen TE: Innate immune response in CF airway epithelia: hyperinflammatory? Am J Physiol Cell Physiol. 2006 Aug;291(2):C218-30. [PubMed:16825601 ]
  16. Lerche A, Svenson M, Wiik A: Cerebrospinal fluid levels of cyclic nucleotides in meningitis and idiopathic polyneuritis. Acta Neurol Scand. 1984 Mar;69(3):168-75. [PubMed:6326460 ]
  17. Ruppert D, Weithmann KU: HL 725, an extremely potent inhibitor of platelet phosphodiesterase and induced platelet aggregation in vitro. Life Sci. 1982 Nov 8;31(19):2037-43. [PubMed:6294426 ]
  18. Tanaka Y, Horinouchi T, Koike K: New insights into beta-adrenoceptors in smooth muscle: distribution of receptor subtypes and molecular mechanisms triggering muscle relaxation. Clin Exp Pharmacol Physiol. 2005 Jul;32(7):503-14. [PubMed:16026507 ]
  19. Fischer JA, Bourne HR, Dambacher MA, Tschopp F, De Meyer R, Devogelaer JP, Werder EA, Nagant De Deuxchaisnes C: Pseudohypoparathyroidism: inheritance and expression of deficient receptor-cyclase coupling protein activity. Clin Endocrinol (Oxf). 1983 Dec;19(6):747-54. [PubMed:6317236 ]
  20. Liu H, Chang L, Chen Y, Xia S, Zhang X: Clinical implication of the changes of cAMP, TXA2 and PGI2 in CSF of asphyxiated newborns. J Huazhong Univ Sci Technolog Med Sci. 2003;23(2):195-7, 200. [PubMed:12973949 ]

Only showing the first 10 proteins. There are 165 proteins in total.

Enzymes

General function:
Involved in transcription cofactor activity
Specific function:
Functions as histone acetyltransferase and regulates transcription via chromatin remodeling. Acetylates all four core histones in nucleosomes. Histone acetylation gives an epigenetic tag for transcriptional activation. Mediates cAMP-gene regulation by binding specifically to phosphorylated CREB protein. Also functions as acetyltransferase for nonhistone targets. Acetylates 'Lys-131' of ALX1 and acts as its coactivator in the presence of CREBBP. Acetylates SIRT2 and is proposed to indirectly increase the transcriptional activity of TP53 through acetylation and subsequent attenuation of SIRT2 deacetylase function. Acetylates HDAC1 leading to its inactivation and modulation of transcription. Acts as a TFAP2A-mediated transcriptional coactivator in presence of CITED2. Plays a role as a coactivator of NEUROD1-dependent transcription of the secretin and p21 genes and controls terminal differentiation of cells in the intestinal epithelium. Promotes cardiac myocyte enlargement. Can also mediate transcriptional repression. Binds to and may be involved in the transforming capacity of the adenovirus E1A protein. In case of HIV-1 infection, it is recruited by the viral protein Tat. Regulates Tat's transactivating activity and may help inducing chromatin remodeling of proviral genes. Acetylates FOXO1 and enhances its transcriptional activity.
Gene Name:
EP300
Uniprot ID:
Q09472
Molecular weight:
264159.725
General function:
Involved in transcription cofactor activity
Specific function:
Acetylates histones, giving a specific tag for transcriptional activation. Also acetylates non-histone proteins, like NCOA3 and FOXO1. Binds specifically to phosphorylated CREB and enhances its transcriptional activity toward cAMP-responsive genes. Acts as a coactivator of ALX1 in the presence of EP300.
Gene Name:
CREBBP
Uniprot ID:
Q92793
Molecular weight:
260991.825
General function:
Involved in catalytic activity
Specific function:
Involved primarily in ATP hydrolysis at the plasma membrane. Plays a role in regulating pyrophosphate levels, and functions in bone mineralization and soft tissue calcification. In vitro, has a broad specificity, hydrolyzing other nucleoside 5' triphosphates such as GTP, CTP, TTP and UTP to their corresponding monophosphates with release of pyrophosphate and diadenosine polyphosphates, and also 3',5'-cAMP to AMP. May also be involved in the regulation of the availability of nucleotide sugars in the endoplasmic reticulum and Golgi, and the regulation of purinergic signaling. Appears to modulate insulin sensitivity.
Gene Name:
ENPP1
Uniprot ID:
P22413
Molecular weight:
104923.58
General function:
Involved in hydrolase activity
Specific function:
In adipose tissue and heart, it primarily hydrolyzes stored triglycerides to free fatty acids, while in steroidogenic tissues, it principally converts cholesteryl esters to free cholesterol for steroid hormone production.
Gene Name:
LIPE
Uniprot ID:
Q05469
Molecular weight:
116596.715
General function:
Involved in 3',5'-cyclic-nucleotide phosphodiesterase activity
Specific function:
Participates in processes of transmission and amplification of the visual signal. cGMP-PDEs are the effector molecules in G-protein-mediated phototransduction in vertebrate rods and cones.
Gene Name:
PDE6H
Uniprot ID:
Q13956
Molecular weight:
9074.36
General function:
Involved in catalytic activity
Specific function:
Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes. Has a higher affinity for cGMP than for cAMP.
Gene Name:
PDE1A
Uniprot ID:
P54750
Molecular weight:
61251.38
Reactions
Cyclic AMP + Water → Adenosine monophosphatedetails
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in maintaining basal levels of the cyclic nucleotide and/or in the cAMP regulation of germ cell development.
Gene Name:
PDE8A
Uniprot ID:
O60658
Molecular weight:
86047.88
Reactions
Cyclic AMP + Water → Adenosine monophosphatedetails
General function:
Involved in catalytic activity
Specific function:
Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes. Has a preference for cGMP as a substrate.
Gene Name:
PDE1B
Uniprot ID:
Q01064
Molecular weight:
61379.235
Reactions
Cyclic AMP + Water → Adenosine monophosphatedetails
General function:
Involved in catalytic activity
Specific function:
Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes. May play a role in fat metabolism. Regulates cAMP binding of RAPGEF3. Through simultaneous binding to RAPGEF3 and PIK3R6 assembles a signaling complex in which the PI3K gamma complex is activated by RAPGEF3 and which is involved in angiogenesis.
Gene Name:
PDE3B
Uniprot ID:
Q13370
Molecular weight:
124332.145
Reactions
Cyclic AMP + Water → Adenosine monophosphatedetails
General function:
Involved in 3',5'-cyclic-AMP phosphodiesterase activity
Specific function:
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May have a role in muscle signal transduction.
Gene Name:
PDE7A
Uniprot ID:
Q13946
Molecular weight:
55504.475
Reactions
Cyclic AMP + Water → Adenosine monophosphatedetails

Transporters

General function:
Involved in anion transport
Specific function:
Electroneutral sodium- and bicarbonate-dependent cotransporter with a Na(+):HCO3(-) 1:1 stoichiometry. Regulates intracellular pH and may play a role in bicarbonate salvage in secretory epithelia. May also have an associated sodium channel activity.
Gene Name:
SLC4A7
Uniprot ID:
Q9Y6M7
Molecular weight:
127358.16
General function:
Involved in ATP binding
Specific function:
May be an organic anion pump relevant to cellular detoxification
Gene Name:
ABCC4
Uniprot ID:
O15439
Molecular weight:
149525.3
References
  1. Chen ZS, Lee K, Kruh GD: Transport of cyclic nucleotides and estradiol 17-beta-D-glucuronide by multidrug resistance protein 4. Resistance to 6-mercaptopurine and 6-thioguanine. J Biol Chem. 2001 Sep 7;276(36):33747-54. Epub 2001 Jul 10. [PubMed:11447229 ]
  2. van Aubel RA, Smeets PH, Peters JG, Bindels RJ, Russel FG: The MRP4/ABCC4 gene encodes a novel apical organic anion transporter in human kidney proximal tubules: putative efflux pump for urinary cAMP and cGMP. J Am Soc Nephrol. 2002 Mar;13(3):595-603. [PubMed:11856762 ]
  3. Chen ZS, Lee K, Walther S, Raftogianis RB, Kuwano M, Zeng H, Kruh GD: Analysis of methotrexate and folate transport by multidrug resistance protein 4 (ABCC4): MRP4 is a component of the methotrexate efflux system. Cancer Res. 2002 Jun 1;62(11):3144-50. [PubMed:12036927 ]
  4. Lai L, Tan TM: Role of glutathione in the multidrug resistance protein 4 (MRP4/ABCC4)-mediated efflux of cAMP and resistance to purine analogues. Biochem J. 2002 Feb 1;361(Pt 3):497-503. [PubMed:11802779 ]
General function:
Involved in ATP binding
Specific function:
Acts as a multispecific organic anion pump which can transport nucleotide analogs
Gene Name:
ABCC5
Uniprot ID:
O15440
Molecular weight:
160658.8
References
  1. Jedlitschky G, Burchell B, Keppler D: The multidrug resistance protein 5 functions as an ATP-dependent export pump for cyclic nucleotides. J Biol Chem. 2000 Sep 29;275(39):30069-74. [PubMed:10893247 ]
General function:
Involved in ion transmembrane transporter activity
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
References
  1. Sekine T, Watanabe N, Hosoyamada M, Kanai Y, Endou H: Expression cloning and characterization of a novel multispecific organic anion transporter. J Biol Chem. 1997 Jul 25;272(30):18526-9. [PubMed:9228014 ]
General function:
Involved in ATP binding
Specific function:
Participates in physiological processes involving bile acids, conjugated steroids and cyclic nucleotides. Enhances the cellular extrusion of cAMP and cGMP. Stimulates the ATP-dependent uptake of a range of physiological and synthetic lipophilic anions, including the glutathione S-conjugates leukotriene C4 and dinitrophenyl S-glutathione, steroid sulfates such as dehydroepiandrosterone 3-sulfate (DHEAS) and estrone 3-sulfate, glucuronides such as estradiol 17-beta-D-glucuronide (E(2)17betaG), the monoanionic bile acids glycocholate and taurocholate, and methotrexate. Probably functions to secrete earwax
Gene Name:
ABCC11
Uniprot ID:
Q96J66
Molecular weight:
154299.6
References
  1. Chen ZS, Guo Y, Belinsky MG, Kotova E, Kruh GD: Transport of bile acids, sulfated steroids, estradiol 17-beta-D-glucuronide, and leukotriene C4 by human multidrug resistance protein 8 (ABCC11). Mol Pharmacol. 2005 Feb;67(2):545-57. Epub 2004 Nov 10. [PubMed:15537867 ]
  2. Guo Y, Kotova E, Chen ZS, Lee K, Hopper-Borge E, Belinsky MG, Kruh GD: MRP8, ATP-binding cassette C11 (ABCC11), is a cyclic nucleotide efflux pump and a resistance factor for fluoropyrimidines 2',3'-dideoxycytidine and 9'-(2'-phosphonylmethoxyethyl)adenine. J Biol Chem. 2003 Aug 8;278(32):29509-14. Epub 2003 May 22. [PubMed:12764137 ]
General function:
Involved in transporter activity
Specific function:
Organic anion transporter, capable of transporting pharmacological substances such as digoxin, ouabain, thyroxine, methotrexate and cAMP. May participate in the regulation of membrane transport of ouabain. Involved in the uptake of the dipeptidyl peptidase-4 inhibitor sitagliptin and hence may play a role in its transport into and out of renal proximal tubule cells. May be involved in the first step of the transport pathway of digoxin and various compounds into the urine in the kidney. May be involved in sperm maturation by enabling directed movement of organic anions and compounds within or between cells. This ion- transporting process is important to maintain the strict epididymal homeostasis necessary for sperm maturation. May have a role in secretory functions since seminal vesicle epithelial cells are assumed to secrete proteins involved in decapacitation by modifying surface proteins to facilitate the acquisition of the ability to fertilize the egg
Gene Name:
SLCO4C1
Uniprot ID:
Q6ZQN7
Molecular weight:
78947.5
General function:
Involved in transmembrane transport
Specific function:
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha- ketoglutarate
Gene Name:
SLC22A7
Uniprot ID:
Q9Y694
Molecular weight:
60025.0
References
  1. Sun W, Wu RR, van Poelje PD, Erion MD: Isolation of a family of organic anion transporters from human liver and kidney. Biochem Biophys Res Commun. 2001 May 4;283(2):417-22. [PubMed:11327718 ]

Only showing the first 10 proteins. There are 165 proteins in total.