You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameCyclic Adenosine Monophosphate
Accession NumberDB02527  (EXPT00959)
TypeSmall Molecule
GroupsExperimental
Description

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).

Structure
Thumb
Synonyms
SynonymLanguageCode
3'-5'-cyclic adenosine monophosphateNot AvailableNot Available
3',5'-Cyclic AMPNot AvailableNot Available
cAMPNot AvailableNot Available
Cyclic adenylic acidNot AvailableNot Available
Cyclic AMPNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number60-92-4
WeightAverage: 329.2059
Monoisotopic: 329.052519653
Chemical FormulaC10H12N5O6P
InChI KeyIVOMOUWHDPKRLL-ASCDQALMSA-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,6S,7S,7aR)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-2-one
SMILES
NC1=NC=NC2=C1N=CN2[C@H]1O[C@@H]2CO[P@](O)(=O)O[C@@H]2[C@@H]1O
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
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Aminopyrimidine
  • Imidolactam
  • Pyrimidine
  • Primary aromatic amine
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Corticotropin Activation of Cortisol ProductionSignalingSMP00310
Vasopressin Regulation of Water HomeostasisSignalingSMP00322
Excitatory Neural Signalling Through 5-HTR 4 and SerotoninSignalingSMP00309
Excitatory Neural Signalling Through 5-HTR 6 and Serotonin SignalingSMP00312
Intracellular Signalling Through Histamine H2 Receptor and HistamineSignalingSMP00335
Excitatory Neural Signalling Through 5-HTR 7 and Serotonin SignalingSMP00311
Intracellular Signalling Through FSH Receptor and Follicle Stimulating HormoneSignalingSMP00333
Intracellular Signalling Through LHCGR Receptor and Luteinizing Hormone/ChoriogonadotropinSignalingSMP00338
Dopamine Activation of Neurological Reward SystemSignalingSMP00308
Intracellular Signalling Through Prostacyclin Receptor and ProstacyclinSignalingSMP00354
Intracellular Signalling Through PGD2 receptor and Prostaglandin D2SignalingSMP00343
Intracellular Signalling Through Adenosine Receptor A2a and AdenosineSignalingSMP00320
Intracellular Signalling Through Adenosine Receptor A2b and AdenosineSignalingSMP00321
Molybdenum Cofactor DeficiencyDiseaseSMP00203
Purine Nucleoside Phosphorylase DeficiencyDiseaseSMP00210
Mitochondrial DNA depletion syndromeDiseaseSMP00536
Mercaptopurine Action PathwayDrug actionSMP00428
Xanthinuria type IDiseaseSMP00512
Gout or Kelley-Seegmiller SyndromeDiseaseSMP00365
Adenosine Deaminase DeficiencyDiseaseSMP00144
AICA-RibosiduriaDiseaseSMP00168
Thioguanine Action PathwayDrug actionSMP00430
Myoadenylate deaminase deficiencyDiseaseSMP00537
Xanthinuria type IIDiseaseSMP00513
Adenine phosphoribosyltransferase deficiency (APRT)DiseaseSMP00535
Lesch-Nyhan Syndrome (LNS)DiseaseSMP00364
Xanthine Dehydrogenase Deficiency (Xanthinuria)DiseaseSMP00220
Purine MetabolismMetabolicSMP00050
Adenylosuccinate Lyase DeficiencyDiseaseSMP00167
Azathioprine Action PathwayDrug actionSMP00427
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9052
Blood Brain Barrier+0.9159
Caco-2 permeable-0.6931
P-glycoprotein substrateNon-substrate0.7464
P-glycoprotein inhibitor INon-inhibitor0.8988
P-glycoprotein inhibitor IINon-inhibitor0.9787
Renal organic cation transporterNon-inhibitor0.9284
CYP450 2C9 substrateNon-substrate0.8462
CYP450 2D6 substrateNon-substrate0.8381
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 substrateNon-inhibitor0.9169
CYP450 2D6 substrateNon-inhibitor0.9295
CYP450 2C19 substrateNon-inhibitor0.9025
CYP450 3A4 substrateNon-inhibitor0.9146
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9319
Ames testNon AMES toxic0.7116
CarcinogenicityNon-carcinogens0.9182
BiodegradationNot ready biodegradable0.9822
Rat acute toxicity2.3314 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9821
hERG inhibition (predictor II)Non-inhibitor0.8361
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point219-220 °CPhysProp
logP-2.96HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility3.58 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity70.29 m3·mol-1ChemAxon
Polarizability28.21 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
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 ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 Q9UL51 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. 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. Pubmed
  3. 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. Pubmed

2. cAMP-dependent protein kinase type I-alpha regulatory subunit

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
cAMP-dependent protein kinase type I-alpha regulatory subunit P10644 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. 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. Pubmed
  3. 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. Pubmed

3. cAMP-dependent protein kinase type II-beta regulatory subunit

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
cAMP-dependent protein kinase type II-beta regulatory subunit P31323 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. 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. Pubmed
  3. 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. Pubmed

4. cAMP-activated global transcriptional regulator CRP

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
cAMP-activated global transcriptional regulator CRP P0ACJ8 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. 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. Pubmed

5. Adenylate cyclase

Kind: protein

Organism: Anabaena sp.

Pharmacological action: unknown

Components

Name UniProt ID Details
Adenylate cyclase P94182 Details

6. Cyclic nucleotide-gated potassium channel mll3241

Kind: protein

Organism: Rhizobium loti (strain MAFF303099)

Pharmacological action: unknown

Components

Name UniProt ID Details
Cyclic nucleotide-gated potassium channel mll3241 Q98GN8 Details

Transporters

1. Multidrug resistance-associated protein 4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Multidrug resistance-associated protein 4 O15439 Details

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
  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
  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
  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

2. Multidrug resistance-associated protein 5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Multidrug resistance-associated protein 5 O15440 Details

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

3. ATP-binding cassette sub-family C member 11

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
ATP-binding cassette sub-family C member 11 Q96J66 Details

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
  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

4. Solute carrier family 22 member 6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Solute carrier family 22 member 6 Q4U2R8 Details

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

5. Solute carrier family 22 member 8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Solute carrier family 22 member 8 Q8TCC7 Details

References:

  1. 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. Pubmed

6. Solute carrier family 22 member 7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Solute carrier family 22 member 7 Q9Y694 Details

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

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:18