Identification
- Generic Name
- Cyclic adenosine monophosphate
- DrugBank Accession Number
- DB02527
- Background
Cyclic adenosine monophosphate (cAMP, cyclic AMP or 3'-5'-cyclic adenosine monophosphate) is a molecule that is important in many biological processes; it is derived from adenosine triphosphate (ATP).
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Cyclic adenosine monophosphate (DB02527)
- Weight
- Average: 329.2059
Monoisotopic: 329.052519653 - Chemical Formula
- C10H12N5O6P
- Synonyms
- 3',5'-cyclic AMP
- Adenosine 3',5'-cyclic monophosphate
- Adenosine 3',5'-cyclic phosphate
- Adenosine 3',5'-phosphate
- AMPC
- cAMP
- Cyclic adenylic acid
- Cyclic AMP
- External IDs
- NSC-143670
- NSC-94017
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UPotassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 Not Available Humans UcAMP-dependent protein kinase type I-alpha regulatory subunit Not Available Humans UcAMP-dependent protein kinase type II-beta regulatory subunit Not Available Humans UcAMP-activated global transcriptional regulator CRP Not Available Escherichia coli (strain K12) UAdenylate cyclase Not Available Anabaena sp. UCyclic nucleotide-gated potassium channel mll3241 Not Available Rhizobium loti (strain MAFF303099) - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcetazolamide The excretion of Cyclic adenosine monophosphate can be decreased when combined with Acetazolamide. Acetylsalicylic acid The excretion of Cyclic adenosine monophosphate can be decreased when combined with Acetylsalicylic acid. Acyclovir The excretion of Cyclic adenosine monophosphate can be decreased when combined with Acyclovir. Adefovir dipivoxil The excretion of Cyclic adenosine monophosphate can be decreased when combined with Adefovir dipivoxil. Aminohippuric acid The excretion of Cyclic adenosine monophosphate can be decreased when combined with Aminohippuric acid. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- 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
- Pentose phosphates / Glycosylamines / 6-aminopurines / Monosaccharide phosphates / Aminopyrimidines and derivatives / Imidolactams / Organic phosphoric acids and derivatives / N-substituted imidazoles / Tetrahydrofurans / Heteroaromatic compounds show 7 more
- Substituents
- 3',5'-cyclic purine ribonucleotide / 6-aminopurine / Alcohol / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Glycosyl compound / Heteroaromatic compound show 23 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- 3',5'-cyclic purine nucleotide, adenyl ribonucleotide (CHEBI:17489) / 3',5'-Cyclic nuclcleotides (C00575)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- E0399OZS9N
- CAS number
- 60-92-4
- InChI Key
- IVOMOUWHDPKRLL-KQYNXXCUSA-N
- InChI
- 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
- IUPAC Name
- (4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-2-one
- SMILES
- NC1=C2N=CN([C@@H]3O[C@@H]4COP(O)(=O)O[C@H]4[C@H]3O)C2=NC=N1
References
- Synthesis Reference
Shigehiro Kataoka, Ayako Nasu, Nobuyuki Yamaji, Motohiko Kato, "Process for preparation of N.sup.6 -substituted 3',5'-cyclic adenosine monophosphate and salt thereof." U.S. Patent US4751293, issued July, 1984.
US4751293- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000058
- KEGG Compound
- C00575
- PubChem Compound
- 6076
- PubChem Substance
- 46508991
- ChemSpider
- 5851
- BindingDB
- 10851
- 1314330
- ChEBI
- 17489
- ChEMBL
- CHEMBL316966
- ZINC
- ZINC000003873977
- PDBe Ligand
- CMP
- Wikipedia
- Cyclic_adenosine_monophosphate
- PDB Entries
- 1cgp / 1cx4 / 1g6n / 1hw5 / 1i5z / 1i6x / 1j59 / 1lb2 / 1lpc / 1nhk … show 131 more
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 219-220 °C PhysProp logP -2.96 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 3.58 mg/mL ALOGPS logP -2.3 ALOGPS logP -3.4 Chemaxon logS -2 ALOGPS pKa (Strongest Acidic) 1.83 Chemaxon pKa (Strongest Basic) 3.94 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 154.84 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 70.29 m3·mol-1 Chemaxon Polarizability 28.42 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9052 Blood Brain Barrier + 0.9159 Caco-2 permeable - 0.6931 P-glycoprotein substrate Non-substrate 0.7464 P-glycoprotein inhibitor I Non-inhibitor 0.8988 P-glycoprotein inhibitor II Non-inhibitor 0.9787 Renal organic cation transporter Non-inhibitor 0.9284 CYP450 2C9 substrate Non-substrate 0.8462 CYP450 2D6 substrate Non-substrate 0.8381 CYP450 3A4 substrate Non-substrate 0.5 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9169 CYP450 2D6 inhibitor Non-inhibitor 0.9295 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.9146 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9319 Ames test Non AMES toxic 0.7116 Carcinogenicity Non-carcinogens 0.9182 Biodegradation Not ready biodegradable 0.9822 Rat acute toxicity 2.3314 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9821 hERG inhibition (predictor II) Non-inhibitor 0.8361
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 181.0194212 predictedDarkChem Lite v0.1.0 [M-H]- 180.6046212 predictedDarkChem Lite v0.1.0 [M-H]- 180.2379212 predictedDarkChem Lite v0.1.0 [M-H]- 180.4967212 predictedDarkChem Lite v0.1.0 [M-H]- 157.68968 predictedDeepCCS 1.0 (2019) [M+H]+ 181.9604212 predictedDarkChem Lite v0.1.0 [M+H]+ 180.9515212 predictedDarkChem Lite v0.1.0 [M+H]+ 180.8979212 predictedDarkChem Lite v0.1.0 [M+H]+ 180.7946212 predictedDarkChem Lite v0.1.0 [M+H]+ 160.00285 predictedDeepCCS 1.0 (2019) [M+Na]+ 181.6395212 predictedDarkChem Lite v0.1.0 [M+Na]+ 180.5679212 predictedDarkChem Lite v0.1.0 [M+Na]+ 180.9689212 predictedDarkChem Lite v0.1.0 [M+Na]+ 165.91539 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Voltage-gated sodium channel activity
- Specific Function
- Hyperpolarization-activated ion channel exhibiting weak selectivity for potassium over sodium ions. Contributes to the native pacemaker currents in heart (If) and in neurons (Ih). Can also transpor...
- Gene Name
- HCN2
- Uniprot ID
- Q9UL51
- Uniprot Name
- Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2
- Molecular Weight
- 96949.43 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Ubiquitin protein ligase binding
- Specific Function
- Regulatory subunit of the cAMP-dependent protein kinases involved in cAMP signaling in cells.
- Gene Name
- PRKAR1A
- Uniprot ID
- P10644
- Uniprot Name
- cAMP-dependent protein kinase type I-alpha regulatory subunit
- Molecular Weight
- 42981.28 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Ubiquitin protein ligase binding
- 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 ...
- Gene Name
- PRKAR2B
- Uniprot ID
- P31323
- Uniprot Name
- cAMP-dependent protein kinase type II-beta regulatory subunit
- Molecular Weight
- 46301.685 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Transcription factor activity, sequence-specific dna binding
- Specific Function
- A global transcription regulator. Complexes with cyclic AMP (cAMP) which allosterically activates DNA binding (to consensus sequence 5'-AAATGTGATCTAGATCACATTT-3') to directly regulate the transcrip...
- Gene Name
- crp
- Uniprot ID
- P0ACJ8
- Uniprot Name
- cAMP-activated global transcriptional regulator CRP
- Molecular Weight
- 23640.275 Da
References
- Kind
- Protein
- Organism
- Anabaena sp.
- Pharmacological action
- Unknown
- General Function
- Nucleotide binding
- Specific Function
- Not Available
- Gene Name
- cyaB2
- Uniprot ID
- P94182
- Uniprot Name
- Adenylate cyclase
- Molecular Weight
- 96773.905 Da
- Kind
- Protein
- Organism
- Rhizobium loti (strain MAFF303099)
- Pharmacological action
- Unknown
- General Function
- Voltage-gated potassium channel activity
- Specific Function
- Cyclic nucleotide-regulated potassium channel activated by cAMP.
- Gene Name
- Not Available
- Uniprot ID
- Q98GN8
- Uniprot Name
- Cyclic nucleotide-gated potassium channel mll3241
- Molecular Weight
- 37735.0 Da
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Atpase activity, coupled to transmembrane movement of substances
- Specific Function
- May be an organic anion pump relevant to cellular detoxification.
- Gene Name
- ABCC4
- Uniprot ID
- O15439
- Uniprot Name
- Multidrug resistance-associated protein 4
- Molecular Weight
- 149525.33 Da
References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Organic anion transmembrane transporter activity
- Specific Function
- Acts as a multispecific organic anion pump which can transport nucleotide analogs.
- Gene Name
- ABCC5
- Uniprot ID
- O15440
- Uniprot Name
- Multidrug resistance-associated protein 5
- Molecular Weight
- 160658.8 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Purine nucleotide transmembrane transporter activity
- 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 ...
- Gene Name
- ABCC11
- Uniprot ID
- Q96J66
- Uniprot Name
- ATP-binding cassette sub-family C member 11
- Molecular Weight
- 154299.625 Da
References
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Sodium-independent organic anion 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 ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
- Gene Name
- SLC22A8
- Uniprot ID
- Q8TCC7
- Uniprot Name
- Solute carrier family 22 member 8
- Molecular Weight
- 59855.585 Da
References
- Cha SH, Sekine T, Fukushima JI, Kanai Y, Kobayashi Y, Goya T, Endou H: Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. Mol Pharmacol. 2001 May;59(5):1277-86. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulf...
- Gene Name
- SLC22A7
- Uniprot ID
- Q9Y694
- Uniprot Name
- Solute carrier family 22 member 7
- Molecular Weight
- 60025.025 Da
References
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at July 02, 2020 13:18