Record Information
Version1.0
Creation date2010-04-08 22:04:59 UTC
Update date2018-05-29 00:33:07 UTC
Primary IDFDB001497
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3' 5'-cyclic AMP
DescriptionCyclic adenosine monophosphate (cAMP) is a second messenger important in many biological processes. cAMP is derived from adenosine triphosphate (ATP) and used for intracellular signal transduction in many different organisms, conveying the cAMP-dependent pathway. 3' 5'-cyclic AMP is found in many foods, some of which are lotus, other cereal product, chicory roots, and peach.
CAS Number60-92-4
Structure
Thumb
Synonyms
SynonymSource
Adenosine 3',5'-cyclic monophosphateChEBI
Adenosine 3',5'-cyclic phosphateChEBI
Adenosine 3',5'-phosphateChEBI
ADENOSINE-3',5'-cyclic-monophosphATEChEBI
Cyclic adenylic acidChEBI
Cyclic AMPChEBI
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 cyclicHMDB
Cyclic AMP, disodium saltHMDB
Cyclic AMP, monopotassium saltHMDB
Cyclic AMP, sodium saltHMDB
AMP, CyclicHMDB
Adenosine cyclic 3',5' monophosphateHMDB
Adenosine cyclic-3',5'-monophosphateHMDB
Cyclic AMP, (R)-isomerHMDB
Cyclic AMP, monosodium saltHMDB
Adenosine cyclic 3',5'-monophosphateHMDB
monoPhosphate, adenosine cyclicHMDB
Adenosine cyclic 3,5 monophosphateHMDB
Cyclic 3',5'-monophosphate, adenosineHMDB
Cyclic AMP, monoammonium saltHMDB
Cyclic monophosphate, adenosineHMDB
Cyclic-3',5'-monophosphate, adenosineHMDB
CAMPChEBI
3',5'-cyclic AMPbiospider
6-(6-amino-9H-Purin-9-yl)tetrahydro-4H-furo[3,2-D][1,3,2]dioxainine-2,7-diol 2-oxideHMDB
Adenosine 3,5'-cyclic monoorateHMDB
Adenosine 3,5'-cyclic monooric acidHMDB
Adenosine 3',5'-ateChEBI
Adenosine 3',5'-cyclic ateChEBI
Adenosine 3',5'-cyclic ic acidGenerator
Adenosine 3',5'-cyclic monoateChEBI
Adenosine 3',5'-cyclic monoic acidGenerator
Adenosine 3',5'-cycloateHMDB
Adenosine 3',5'-cyclophosphoric acidbiospider
Adenosine 3',5'-ic acidGenerator
Adenosine 3',5'-monoateHMDB
Adenosine cyclic 3',5'-phosphatebiospider
Adenosine cyclic monoateHMDB
Adenosine cyclic-monoateHMDB
ADENOSINE-3',5'-cyclic-monoATEChEBI
ADENOSINE-3',5'-cyclic-monoic acidGenerator
Adenosine-cyclic-ateHMDB
Adenosine-cyclic-oric-acidHMDB
Adenosine, 3',5'-cyclic-monophosphoric acidbiospider
Cyclic adenosine 3',5'-ateHMDB
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
Chemical FormulaC10H12N5O6P
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
InChI IdentifierInChI=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
Isomeric SMILESNC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(O)(=O)O[C@H]2[C@H]1O
Average Molecular Weight329.2059
Monoisotopic Molecular Weight329.052519653
Classification
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.
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point219-220 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP-2.96HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
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
ChemSpider ID5851
ChEMBL IDCHEMBL316966
KEGG Compound IDC00575
Pubchem Compound ID6076
Pubchem Substance IDNot Available
ChEBI ID17489
Phenol-Explorer IDNot Available
DrugBank IDDB02527
HMDB IDHMDB00058
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDCYCLIC-AMP
BIGG ID1484809
KNApSAcK IDC00001497
HET IDCMP
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCyclic AMP
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Retinal cone rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gammaPDE6HQ13956
Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1BPDE1BQ01064
cGMP-inhibited 3',5'-cyclic phosphodiesterase BPDE3BQ13370
Retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gammaPDE6GP18545
Retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit deltaPDE6DO43924
Pathways
NameSMPDB LinkKEGG Link
Purine MetabolismSMP00050 map00230
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).