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Showing metabocard for Cyclic AMP (BMDB0000058)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 1.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2016-09-30 22:19:06 UTC | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2020-05-21 16:29:08 UTC | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
BMDB ID | BMDB0000058 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Metabolite Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Common Name | Cyclic AMP | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | 3',5'-Cyclic AMP, also known as cyclic AMP or camp, 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. 3',5'-Cyclic AMP exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. 3',5'-Cyclic AMP exists in all living species, ranging from bacteria to humans. In cattle, 3',5'-cyclic AMP is involved in the metabolic pathway called the lysophosphatidic Acid LPA6 signalling pathway. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms |
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Chemical Formula | C10H12N5O6P | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Average Molecular Weight | 329.2059 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Monoisotopic Molecular Weight | 329.052519653 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional Name | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS Registry Number | 60-92-4 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | 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. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Nucleosides, nucleotides, and analogues | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Purine nucleotides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Cyclic purine nucleotides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | 3',5'-cyclic purine nucleotides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents |
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Substituents |
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Molecular Framework | Aromatic heteropolycyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Ontology | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Status | Detected but not Quantified | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Origin |
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Biofunction | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Application | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular locations |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties |
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Predicted Properties | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations |
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Biospecimen Locations |
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Pathways | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Normal Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Abnormal Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
HMDB ID | HMDB0000058 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
DrugBank ID | DB02527 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Phenol Explorer Compound ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
FooDB ID | FDB030763 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
KNApSAcK ID | C00001497 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemspider ID | 5851 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
KEGG Compound ID | C00575 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
BioCyc ID | CAMP | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
BiGG ID | 1484809 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Wikipedia Link | Cyclic_AMP | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
METLIN ID | 5120 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
PubChem Compound | 6076 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
PDB ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
ChEBI ID | 17489 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
General References |
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Enzymes
- General function:
- Signal transduction mechanisms
- Specific function:
- Catalyzes the formation of the signaling molecule cAMP in response to G-protein signaling (PubMed:2472670, PubMed:2022671. PubMed:19029295). Mediates responses to increased cellular Ca(2+)/calmodulin levels (PubMed:2022671, PubMed:19029295). May be involved in regulatory processes in the central nervous system. May play a role in memory and learning. Plays a role in the regulation of the circadian rhythm of daytime contrast sensitivity probably by modulating the rhythmic synthesis of cyclic AMP in the retina (By similarity).
- Gene Name:
- ADCY1
- Uniprot ID:
- P19754
- Molecular weight:
- 123979.0
Reactions
Adenosine triphosphate → Cyclic AMP + Pyrophosphate | details |
- General function:
- Signal transduction mechanisms
- Specific function:
- Regulatory subunit of the cAMP-dependent protein kinases involved in cAMP signaling in cells. Type II regulatory chains mediate membrane association by binding to anchoring proteins, including the MAP2 kinase (By similarity).
- Gene Name:
- PRKAR2A
- Uniprot ID:
- P00515
- Molecular weight:
- 45094.0
- General function:
- Not Available
- Specific function:
- Extremely potent competitive inhibitor of cAMP-dependent protein kinase activity, this protein interacts with the catalytic subunit of the enzyme after the cAMP-induced dissociation of its regulatory chains.
- Gene Name:
- PKIA
- Uniprot ID:
- Q3SX13
- Molecular weight:
- 8016.0
- General function:
- Signal transduction mechanisms
- Specific function:
- Regulatory subunit of the cAMP-dependent protein kinases involved in cAMP signaling in cells.
- Gene Name:
- PRKAR1A
- Uniprot ID:
- P00514
- Molecular weight:
- 42893.0
- General function:
- Signal transduction mechanisms
- Specific function:
- Regulatory subunit of the cAMP-dependent protein kinases involved in cAMP signaling in cells. Type II regulatory chains mediate membrane association by binding to anchoring proteins, including the MAP2 kinase.
- Gene Name:
- PRKAR2B
- Uniprot ID:
- P31322
- Molecular weight:
- 46336.0
- General function:
- Involved in ATP binding
- Specific function:
- Mediates cAMP-dependent signaling triggered by receptor binding to GPCRs. PKA activation regulates diverse cellular processes such as cell proliferation, the cell cycle, and differentiation and regulation of microtubule dynamics, chromatin condensation and decondensation, nuclear envelope disassembly and reassembly, as well as regulation of intracellular transport mechanisms and ion flux. Regulates the abundance of compartmentalized pools of its regulatory subunits through phosphorylation of PJA2 which binds and ubiquitinates these subunits, leading to their subsequent proteolysis. Phosphorylates GPKOW which regulates its ability to bind RNA.
- Gene Name:
- PRKACB
- Uniprot ID:
- P05131
- Molecular weight:
- 40594.0
Reactions
Cyclic AMP → Cyclic AMP + cAMP-dependent protein kinase catalytic subunit beta | details |
- General function:
- Involved in G-protein coupled receptor protein signalin
- Specific function:
- Receptor for prostaglandin D2 (PGD2). The activity of this receptor is mainly mediated by G(s) proteins that stimulate adenylate cyclase, resulting in an elevation of intracellular cAMP. A mobilization of calcium is also observed, but without formation of inositol 1,4,5-trisphosphate (By similarity).
- Gene Name:
- PTGDR
- Uniprot ID:
- A5D7K8
- Molecular weight:
- 40372.0
- General function:
- Involved in protein dimerization activity
- Specific function:
- Phosphorylation-dependent transcription factor that stimulates transcription upon binding to the DNA cAMP response element (CRE), a sequence present in many viral and cellular promoters. Transcription activation is enhanced by the TORC coactivators which act independently of Ser-117 phosphorylation. Involved in different cellular processes including the synchronization of circadian rhythmicity and the differentiation of adipose cells.
- Gene Name:
- CREB1
- Uniprot ID:
- P27925
- Molecular weight:
- 34877.0
- General function:
- Involved in protein dimerization activity
- Specific function:
- Transcription factor that may act during endoplasmic reticulum stress by activating unfolded protein response target genes. Activated in response to cAMP stimulation. In vitro, binds the cAMP response element (CRE). Activates transcription through box-B element and CRE. Seems to function synergistically with ATF6. In acute inflammatory response, may activate expression of acute phase response (APR) genes. May be involved in growth suppression (By similarity).
- Gene Name:
- CREB3L3
- Uniprot ID:
- Q3SYZ3
- Molecular weight:
- 48689.0
- General function:
- Involved in sequence-specific DNA binding
- Specific function:
- Not Available
- Gene Name:
- CREBL1
- Uniprot ID:
- Q3KUS1
- Molecular weight:
- 6489.0
- General function:
- Involved in G-protein coupled receptor activity
- Specific function:
- Receptor for bile acid. Bile acid-binding induces its internalization, activation of extracellular signal-regulated kinase and intracellular cAMP production. May be involved in the suppression of macrophage functions by bile acids. Involved in bile acid promoted GLP1R secretion (By similarity).
- Gene Name:
- GPBAR1
- Uniprot ID:
- Q862A9
- Molecular weight:
- 35104.0
- General function:
- Involved in protein dimerization activity
- Specific function:
- This protein binds the cAMP response element (CRE) (consensus: 5'-GTGACGT[AC][AG]-3'), a sequence present in many viral and cellular promoters. Mediates PKA-induced stimulation of CRE-reporter genes. Represses the expression of FTH1 and other antioxidant detoxification genes. Triggers cell proliferation and transformation (By similarity).
- Gene Name:
- ATF1
- Uniprot ID:
- Q08DA8
- Molecular weight:
- 29261.0
- General function:
- Involved in protein dimerization activity
- Specific function:
- Transcriptional regulator that binds the cAMP response element (CRE), a sequence present in many viral and cellular promoters. Isoforms are either transcriptional activators or repressors. Isoform 1 and isoform 2 are transcriptional activators. Plays a role in spermatogenesis and is involved in spermatid maturation (By similarity).
- Gene Name:
- CREM
- Uniprot ID:
- Q1LZH5
- Molecular weight:
- 38694.0
- General function:
- Signal transduction mechanisms
- Specific function:
- Odorant signal transduction is probably mediated by a G-protein coupled cascade using cAMP as second messenger. The olfactory channel can be shown to be activated by cyclic nucleotides which leads to a depolarization of olfactory sensory neurons.
- Gene Name:
- CNGA2
- Uniprot ID:
- Q03041
- Molecular weight:
- 76014.0
- General function:
- Involved in protein dimerization activity
- Specific function:
- This protein binds the cAMP response element (CRE) (consensus: 5'-GTGACGT[AC][AG]-3'), a sequence present in many viral and cellular promoters. Represses transcription from promoters with ATF sites. It may repress transcription by stabilizing the binding of inhibitory cofactors at the promoter (By similarity).
- Gene Name:
- ATF3
- Uniprot ID:
- Q2KII1
- Molecular weight:
- 20567.0
- General function:
- Involved in protein dimerization activity
- Specific function:
- Transcriptional activator. Binds the cAMP response element (CRE) (consensus: 5'-GTGACGT[AC][AG]-3'), a sequence present in many viral and cellular promoters. Cooperates with FOXO1 in osteoblasts to regulate glucose homeostasis through suppression of beta-cell production and decrease in insulin production. Regulates the induction of DDIT3/CHOP and asparagine synthetase (ASNS) in response to endoplasmic reticulum (ER) stress. In concert with DDIT3/CHOP, activates the transcription of TRIB3 and promotes ER stress-induced neuronal apoptosis by regulating the transcriptional induction of BBC3/PUMA. Activates transcription of SIRT4. Regulates the circadian expression of the core clock component PER2 and the serotonin transporter SLC6A4. Binds in a circadian time-dependent manner to the cAMP response elements (CRE) in the SLC6A4 and PER2 promoters and periodically activates the transcription of these genes. During ER stress response, activates the transcription of NLRP1, possibly in concert with other factors.
- Gene Name:
- ATF4
- Uniprot ID:
- Q3ZCH6
- Molecular weight:
- 38245.0
- General function:
- Involved in protein dimerization activity
- Specific function:
- Endoplasmic reticulum (ER)-bound sequence-specific transcription factor that directly binds DNA and activates transcription. Plays a role in the unfolded protein response (UPR), promoting cell survival versus ER stress-induced apoptotic cell death. Also involved in cell proliferation, migration and differentiation, tumor suppression and inflammatory gene expression. Acts as a positive regulator of LKN-1/CCL15-induced chemotaxis signaling of leukocyte cell migration. Associates with chromatin to the HERPUD1 promoter. Also induces transcriptional activation of chemokine receptors. Functions as a negative transcriptional regulator in ligand-induced transcriptional activation of the glucocorticoid receptor NR3C1 by recruiting and activating histone deacetylases (HDAC1, HDAC2 and HDAC6). Also decreases the acetylation level of histone H4. Does not promote the chemotactic activity of leukocyte cells.
- Gene Name:
- CREB3
- Uniprot ID:
- Q8SQ19
- Molecular weight:
- 40912.0
- General function:
- Involved in cAMP binding
- Specific function:
- Subunit of cyclic nucleotide-gated (CNG) channels, nonselective cation channels, which play important roles in both visual and olfactory signal transduction. When associated with CNGA1, it is involved in the regulation of ion flow into the rod photoreceptor outer segment (ROS), in response to light-induced alteration of the levels of intracellular cGMP (By similarity).
- Gene Name:
- CNGB1
- Uniprot ID:
- Q28181
- Molecular weight:
- 155065.0
- General function:
- Involved in DNA binding
- Specific function:
- Binds cAMP regulatory element DNA sequence. May play a role in RNA splicing (By similarity).
- Gene Name:
- LUC7L3
- Uniprot ID:
- Q3SX41
- Molecular weight:
- 51496.0
- General function:
- Involved in hormone-mediated signaling
- Specific function:
- Involved in the regulation of melanogenesis. The binding of ASP to MC1R precludes alpha-MSH initiated signaling and thus blocks production of cAMP, leading to a down-regulation of eumelanogenesis (brown/black pigment) and thus increasing synthesis of pheomelanin (yellow/red pigment) (By similarity).
- Gene Name:
- ASIP
- Uniprot ID:
- Q29414
- Molecular weight:
- 14841.0
- General function:
- Not Available
- Specific function:
- Transcriptional coactivator for CREB1 which activates transcription through both consensus and variant cAMP response element (CRE) sites. Acts as a coactivator, in the SIK/TORC signaling pathway, being active when dephosphorylated and acts independently of CREB1 'Ser-133' phosphorylation. Enhances the interaction of CREB1 with TAF4. Regulates gluconeogenesis as a component of the LKB1/AMPK/TORC2 signaling pathway. Regulates the expression of specific genes such as the steroidogenic gene, StAR. Potent coactivator of PPARGC1A and inducer of mitochondrial biogenesis in muscle cells (By similarity).
- Gene Name:
- CRTC2
- Uniprot ID:
- Q08E26
- Molecular weight:
- 72818.0
- General function:
- Involved in protein dimerization activity
- Specific function:
- Not Available
- Gene Name:
- CREB1
- Uniprot ID:
- Q0V7N6
- Molecular weight:
- 35109.0
- General function:
- Not Available
- Specific function:
- Functions as a guanine nucleotide exchange factor (GEF), which activates Rap and Ras family of small GTPases by exchanging bound GDP for free GTP in a cAMP-dependent manner. Serves as a link between cell surface receptors and Rap/Ras GTPases in intracellular signaling cascades. Acts also as an effector for Rap1 by direct association with Rap1-GTP thereby leading to the amplification of Rap1-mediated signaling. Shows weak activity on HRAS. It is controversial whether RAPGEF2 binds cAMP and cGMP or not. Its binding to ligand-activated beta-1 adrenergic receptor ADRB1 leads to the Ras activation through the G(s)-alpha signaling pathway. Involved in the cAMP-induced Ras and Erk1/2 signaling pathway that leads to sustained inhibition of long term melanogenesis by reducing dendrite extension and melanin synthesis. Provides also inhibitory signals for cell proliferation of melanoma cells and promotes their apoptosis in a cAMP-independent nanner. Regulates cAMP-induced neuritogenesis by mediating the Rap1/B-Raf/ERK signaling through a pathway that is independent on both PKA and RAPGEF3/RAPGEF4. Involved in neuron migration and in the formation of the major forebrain fiber connections forming the corpus callosum, the anterior commissure and the hippocampal commissure during brain development. Involved in neuronal growth factor (NGF)-induced sustained activation of Rap1 at late endosomes and in brain-derived neurotrophic factor (BDNF)-induced axon outgrowth of hippocampal neurons. Plays a role in the regulation of embryonic blood vessel formation and in the establishment of basal junction integrity and endothelial barrier function. May be involved in the regulation of the vascular endothelial growth factor receptor KDR and cadherin CDH5 expression at allantois endothelial cell-cell junctions (By similarity). Binds to cAMP.
- Gene Name:
- RAPGEF2
- Uniprot ID:
- F1MSG6
- Molecular weight:
- 165144.0
Reactions
Cyclic AMP + Rap guanine nucleotide exchange factor 3 + Guanosine triphosphate + Ras-related protein Rap-1A → Guanosine diphosphate + Ras-related protein Rap-1A | details |
- General function:
- Not Available
- 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 (By similarity).
- Gene Name:
- PDE1A
- Uniprot ID:
- P14100
- Molecular weight:
- 60843.0
Reactions
Cyclic AMP + Water → Adenosine monophosphate | details |