Human Metabolome Database Version 3.5

Showing metabocard for Cyclic AMP (HMDB00058)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:49 -0700
HMDB ID HMDB00058
Secondary Accession Numbers None
Metabolite Identification
Common Name Cyclic AMP
Description Cyclic 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3'5'-Cyclic AMP
  2. 6-(6-Amino-9H-purin-9-yl)tetrahydro-4H-furo[3,2-D][1,3,2]dioxaphosphinine-2,7-diol 2-oxide
  3. Acrasin
  4. Adenosine 3',5'-cyclic monophosphate
  5. Adenosine 3',5'-cyclic phosphate
  6. Adenosine 3',5'-cyclophosphate
  7. Adenosine 3',5'-monophosphate
  8. Adenosine 3,5'-cyclic monophosphorate
  9. Adenosine 3,5'-cyclic monophosphoric acid
  10. Adenosine cyclic monophosphate
  11. Adenosine cyclic-monophosphate
  12. Adenosine-cyclic-phosphate
  13. Adenosine-cyclic-phosphoric-acid
  14. cAMP
  15. Cyclic 3',5'-adenylate
  16. Cyclic 3',5'-adenylic acid
  17. Cyclic 3',5'-AMP
  18. Cyclic adenosine 3',5'-phosphate
  19. Cyclic AMP
Chemical Formula C10H12N5O6P
Average Molecular Weight 329.2059
Monoisotopic Molecular Weight 329.052519653
IUPAC Name (4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-1,3,5,2$l^{5}-furo[3,2-d][1,3,2$l^{5}]dioxaphosphinin-2-one
Traditional IUPAC Name 3',5'-cyclic amp
CAS Registry Number 60-92-4
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 Key IVOMOUWHDPKRLL-KQYNXXCUSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Purine Nucleotides
Sub Class Cyclic Purine Nucleotides
Other Descriptors
  • 3',5'-Cyclic nuclcleotides(KEGG)
  • 3',5'-cyclic purine nucleotide(ChEBI)
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1 Phosphoribosyl Imidazole
  • Aminopyrimidine
  • Imidazole
  • Imidazopyrimidine
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxolane
  • Phosphoric Acid Ester
  • Purine
  • Pyrimidine
  • Secondary Alcohol
Direct Parent 3',5'-cyclic Purine Nucleotides
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Purine metabolism
  • Second messenger
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Golgi apparatus
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 219 - 220 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 4 mg/mL Not Available
LogP -2.96 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 3.58 g/L ALOGPS
LogP -2.29 ALOGPS
LogP -3.8 ChemAxon
LogS -1.96 ALOGPS
pKa (strongest acidic) 1.83 ChemAxon
pKa (strongest basic) 4.99 ChemAxon
Hydrogen Acceptor Count 8 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 154.84 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 70.29 ChemAxon
Polarizability 28.22 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Golgi apparatus
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • All Tissues
Pathways
Name SMPDB Link KEGG Link
Purine Metabolism SMP00050 map00230 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.0085 +/- 0.0005 uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.020 +/- 0.004 uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.020+/- 0.004 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.024 (0.022-0.026) uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.021 +/- 0.008 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
0.020 (0.016-0.024) uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.38 +/- 0.14 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.22 +/- 0.055 umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.0077 +/- 0.0003 uM Adult (>18 years old) Male Sildenafil-induced headache
Cerebrospinal Fluid (CSF) Detected and Quantified 0.0110 +/- 0.0028 uM Adult (>18 years old) Both Idiopathic polyneuritis
Cerebrospinal Fluid (CSF) Detected and Quantified 0.033 +/- 0.012 uM Adult (>18 years old) Not Specified Comment Meningitis
Cerebrospinal Fluid (CSF) Detected and Quantified 0.00860 (0.00620-0.0110) uM Adult (>18 years old) Both Comment Hypoxic-ischemic encephalopathy
Cerebrospinal Fluid (CSF) Detected and Quantified 0.014 (0.012-0.017) uM Adult (>18 years old) Both Comment Hypoxic-ischemic encephalopathy
Cerebrospinal Fluid (CSF) Detected and Quantified 0.0202 +/- 0.004 uM Adult (>18 years old) Not Specified Initial slight suspicion of meningitis with normal CSF
Cerebrospinal Fluid (CSF) Detected and Quantified 0.034 (0.021-0.046) uM Adult (>18 years old) Both Comment Meningitis
Cerebrospinal Fluid (CSF) Detected and Quantified 0.011 (0.0082-0.014) uM Adult (>18 years old) Both Idiopathic polyneuritis
Urine Detected and Quantified 0.24 +/- 0.028 umol/mmol creatinine Adult (>18 years old) Both Chronic renal failure
Associated Disorders and Diseases
Disease References
Idiopathic polyneuritis
  • 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 Link_out
      Hypoxic-ischemic encephalopathy
      • 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 Link_out
          Meningitis
          • 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 Link_out
              Headache
              • 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 Link_out
                  Chronic renal failure
                  • 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 Link_out
                      Associated OMIM IDs None
                      DrugBank ID DB02527 Link_out
                      DrugBank Metabolite ID Not Available
                      Phenol Explorer Compound ID Not Available
                      Phenol Explorer Metabolite ID Not Available
                      FoodDB ID FDB001497
                      KNApSAcK ID C00001497 Link_out
                      Chemspider ID 5851 Link_out
                      KEGG Compound ID C00575 Link_out
                      BioCyc ID CAMP Link_out
                      BiGG ID 1484809 Link_out
                      Wikipedia Link Cyclic AMP Link_out
                      NuGOwiki Link HMDB00058 Link_out
                      Metagene Link HMDB00058 Link_out
                      METLIN ID 5120 Link_out
                      PubChem Compound 6076 Link_out
                      PDB ID CMP Link_out
                      ChEBI ID 17489 Link_out
                      References
                      Synthesis Reference Genieser, 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 Link_out
                      2. Wine JJ, Joo NS: Submucosal glands and airway defense. Proc Am Thorac Soc. 2004;1(1):47-53. Pubmed: 16113412 Link_out
                      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 Link_out
                      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 Link_out
                      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 Link_out
                      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 Link_out
                      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 Link_out
                      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 Link_out
                      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 Link_out
                      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 Link_out
                      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 Link_out
                      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 Link_out
                      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 Link_out
                      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 Link_out
                      15. Machen TE: Innate immune response in CF airway epithelia: hyperinflammatory? Am J Physiol Cell Physiol. 2006 Aug;291(2):C218-30. Pubmed: 16825601 Link_out
                      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 Link_out
                      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 Link_out
                      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 Link_out
                      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 Link_out
                      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 Link_out

                      Enzymes

                      Show all enzymes and transporters Important Only showing the first 50 enzymes. There are 158 enzymes in total.

                      Name: Histone acetyltransferase p300
                      Reactions: Not Available
                      Gene Name: EP300
                      Uniprot ID: Q09472 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: CREB-binding protein
                      Reactions: Not Available
                      Gene Name: CREBBP
                      Uniprot ID: Q92793 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 1
                      Reactions: Not Available
                      Gene Name: ENPP1
                      Uniprot ID: P22413 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Hormone-sensitive lipase
                      Reactions: Not Available
                      Gene Name: LIPE
                      Uniprot ID: Q05469 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Retinal cone rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma
                      Reactions: Not Available
                      Gene Name: PDE6H
                      Uniprot ID: Q13956 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1A
                      Reactions:
                      Cyclic AMP + Water unknown Adenosine monophosphate details
                      Gene Name: PDE1A
                      Uniprot ID: P54750 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8A
                      Reactions:
                      Cyclic AMP + Water unknown Adenosine monophosphate details
                      Gene Name: PDE8A
                      Uniprot ID: O60658 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1B
                      Reactions:
                      Cyclic AMP + Water unknown Adenosine monophosphate details
                      Gene Name: PDE1B
                      Uniprot ID: Q01064 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: cGMP-inhibited 3',5'-cyclic phosphodiesterase B
                      Reactions:
                      Cyclic AMP + Water unknown Adenosine monophosphate details
                      Gene Name: PDE3B
                      Uniprot ID: Q13370 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: High affinity cAMP-specific 3',5'-cyclic phosphodiesterase 7A
                      Reactions:
                      Cyclic AMP + Water unknown Adenosine monophosphate details
                      Gene Name: PDE7A
                      Uniprot ID: Q13946 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: cGMP-inhibited 3',5'-cyclic phosphodiesterase A
                      Reactions:
                      Cyclic AMP + Water unknown Adenosine monophosphate details
                      Gene Name: PDE3A
                      Uniprot ID: Q14432 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A
                      Reactions:
                      Cyclic AMP + Water unknown Adenosine monophosphate details
                      Gene Name: PDE10A
                      Uniprot ID: Q9Y233 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1C
                      Reactions:
                      Cyclic AMP + Water unknown Adenosine monophosphate details
                      Gene Name: PDE1C
                      Uniprot ID: Q14123 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: cAMP-specific 3',5'-cyclic phosphodiesterase 4B
                      Reactions:
                      Cyclic AMP + Water unknown Adenosine monophosphate details
                      Gene Name: PDE4B
                      Uniprot ID: Q07343 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: cAMP-specific 3',5'-cyclic phosphodiesterase 7B
                      Reactions:
                      Cyclic AMP + Water unknown Adenosine monophosphate details
                      Gene Name: PDE7B
                      Uniprot ID: Q9NP56 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A
                      Reactions: Not Available
                      Gene Name: PDE9A
                      Uniprot ID: O76083 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: cGMP-dependent 3',5'-cyclic phosphodiesterase
                      Reactions:
                      Cyclic AMP + Water unknown Adenosine monophosphate details
                      Gene Name: PDE2A
                      Uniprot ID: O00408 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8B
                      Reactions:
                      Cyclic AMP + Water unknown Adenosine monophosphate details
                      Gene Name: PDE8B
                      Uniprot ID: O95263 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: cAMP-specific 3',5'-cyclic phosphodiesterase 4C
                      Reactions:
                      Cyclic AMP + Water unknown Adenosine monophosphate details
                      Gene Name: PDE4C
                      Uniprot ID: Q08493 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: cAMP-specific 3',5'-cyclic phosphodiesterase 4D
                      Reactions:
                      Cyclic AMP + Water unknown Adenosine monophosphate details
                      Gene Name: PDE4D
                      Uniprot ID: Q08499 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma
                      Reactions: Not Available
                      Gene Name: PDE6G
                      Uniprot ID: P18545 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit delta
                      Reactions: Not Available
                      Gene Name: PDE6D
                      Uniprot ID: O43924 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: cAMP-specific 3',5'-cyclic phosphodiesterase 4A
                      Reactions:
                      Cyclic AMP + Water unknown Adenosine monophosphate details
                      Gene Name: PDE4A
                      Uniprot ID: P27815 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: cGMP-specific 3',5'-cyclic phosphodiesterase
                      Reactions: Not Available
                      Gene Name: PDE5A
                      Uniprot ID: O76074 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Adenylate cyclase type 7
                      Reactions:
                      Adenosine triphosphate unknown Cyclic AMP + Pyrophosphate details
                      Gene Name: ADCY7
                      Uniprot ID: P51828 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Adenylate cyclase type 4
                      Reactions:
                      Adenosine triphosphate unknown Cyclic AMP + Pyrophosphate details
                      Gene Name: ADCY4
                      Uniprot ID: Q8NFM4 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Adenylate cyclase type 6
                      Reactions:
                      Adenosine triphosphate unknown Cyclic AMP + Pyrophosphate details
                      Gene Name: ADCY6
                      Uniprot ID: O43306 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Adenylate cyclase type 5
                      Reactions:
                      Adenosine triphosphate unknown Cyclic AMP + Pyrophosphate details
                      Gene Name: ADCY5
                      Uniprot ID: O95622 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Adenylate cyclase type 8
                      Reactions:
                      Adenosine triphosphate unknown Cyclic AMP + Pyrophosphate details
                      Gene Name: ADCY8
                      Uniprot ID: P40145 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Adenylate cyclase type 9
                      Reactions:
                      Adenosine triphosphate unknown Cyclic AMP + Pyrophosphate details
                      Gene Name: ADCY9
                      Uniprot ID: O60503 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Adenylate cyclase type 3
                      Reactions:
                      Adenosine triphosphate unknown Cyclic AMP + Pyrophosphate details
                      Gene Name: ADCY3
                      Uniprot ID: O60266 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Adenylate cyclase type 1
                      Reactions:
                      Adenosine triphosphate unknown Cyclic AMP + Pyrophosphate details
                      Gene Name: ADCY1
                      Uniprot ID: Q08828 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Adenylate cyclase type 2
                      Reactions:
                      Adenosine triphosphate unknown Cyclic AMP + Pyrophosphate details
                      Gene Name: ADCY2
                      Uniprot ID: Q08462 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Steroid 17-alpha-hydroxylase/17,20 lyase
                      Reactions: Not Available
                      Gene Name: CYP17A1
                      Uniprot ID: P05093 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Cyclic nucleotide-gated cation channel alpha-3
                      Reactions: Not Available
                      Gene Name: CNGA3
                      Uniprot ID: Q16281 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Cyclic nucleotide-gated cation channel beta-3
                      Reactions: Not Available
                      Gene Name: CNGB3
                      Uniprot ID: Q9NQW8 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Rap guanine nucleotide exchange factor 2
                      Reactions: Not Available
                      Gene Name: RAPGEF2
                      Uniprot ID: Q9Y4G8 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 1
                      Reactions: Not Available
                      Gene Name: HCN1
                      Uniprot ID: O60741 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: cAMP-dependent protein kinase catalytic subunit gamma
                      Reactions: Not Available
                      Gene Name: PRKACG
                      Uniprot ID: P22612 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: cAMP-dependent protein kinase catalytic subunit alpha
                      Reactions: Not Available
                      Gene Name: PRKACA
                      Uniprot ID: P17612 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Serine/threonine-protein kinase PRKY
                      Reactions: Not Available
                      Gene Name: PRKY
                      Uniprot ID: O43930 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: cAMP-dependent protein kinase catalytic subunit beta
                      Reactions: Not Available
                      Gene Name: PRKACB
                      Uniprot ID: P22694 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Ribosomal protein S6 kinase alpha-5
                      Reactions: Not Available
                      Gene Name: RPS6KA5
                      Uniprot ID: O75582 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Serine/threonine-protein kinase PRKX
                      Reactions: Not Available
                      Gene Name: PRKX
                      Uniprot ID: P51817 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Serine/threonine-protein kinase 11
                      Reactions: Not Available
                      Gene Name: STK11
                      Uniprot ID: Q15831 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: ATP-binding cassette sub-family A member 1
                      Reactions: Not Available
                      Gene Name: ABCA1
                      Uniprot ID: O95477 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Na(+)/H(+) exchange regulatory cofactor NHE-RF1
                      Reactions: Not Available
                      Gene Name: SLC9A3R1
                      Uniprot ID: O14745 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Aryl hydrocarbon receptor
                      Reactions: Not Available
                      Gene Name: AHR
                      Uniprot ID: P35869 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Cyclic AMP-responsive element-binding protein 5
                      Reactions: Not Available
                      Gene Name: CREB5
                      Uniprot ID: Q02930 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Class E basic helix-loop-helix protein 40
                      Reactions: Not Available
                      Gene Name: BHLHE40
                      Uniprot ID: O14503 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Transporters
                      Name: Sodium bicarbonate cotransporter 3
                      Reactions: Not Available
                      Gene Name: SLC4A7
                      Uniprot ID: Q9Y6M7 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Multidrug resistance-associated protein 4
                      Reactions: Not Available
                      Gene Name: ABCC4
                      Uniprot ID: O15439 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Multidrug resistance-associated protein 5
                      Reactions: Not Available
                      Gene Name: ABCC5
                      Uniprot ID: O15440 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Solute carrier family 22 member 6
                      Reactions: Not Available
                      Gene Name: SLC22A6
                      Uniprot ID: Q4U2R8 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: ATP-binding cassette sub-family C member 11
                      Reactions: Not Available
                      Gene Name: ABCC11
                      Uniprot ID: Q96J66 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Solute carrier organic anion transporter family member 4C1
                      Reactions: Not Available
                      Gene Name: SLCO4C1
                      Uniprot ID: Q6ZQN7 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Solute carrier family 22 member 7
                      Reactions: Not Available
                      Gene Name: SLC22A7
                      Uniprot ID: Q9Y694 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA