P. aeruginosa Metabolome Database: cyclic-AMP (PAMDB110476)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB110476

Identification

Name:

cyclic-AMP

Description:

An organophosphate oxoanion that is the conjugate base of 3',5'-cyclic AMP arising from deprotonation of the free phosphate OH group; major species at pH 7.3.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

cyclic 3',5'-AMP
3',5'-cyclic AMP
adenosine cyclic-3',5'-monophosphate
adenosine cyclic-monophosphate
adenosine-cyclic-phosphoric-acid
cAMP
adenosine-cyclic-phosphate
adenosine-3',5'-monophosphate
adenosine 3',5'-cyclic phosphate
adenosine-3',5'-cyclic monophosphate
cyclic-3',5'-adenosine monophosphate

Chemical Formula:

C₁₀H₁₁N₅O₆P

Average Molecular Weight:

328.2

Monoisotopic Molecular Weight:

329.0525196538

InChI Key:

IVOMOUWHDPKRLL-KQYNXXCUSA-M

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)/p-1/t4-,6-,7-,10-/m1/s1

CAS number:

60-92-4

IUPAC Name:

adenosine 3',5'-phosphate

Traditional IUPAC Name:

cyclic adenosine monophosphate

SMILES:

C1(OP(=O)([O-])OC2(C(O)C(OC12)N4(C=NC3(C(N)=NC=NC=34))))

Chemical Taxonomy

Taxonomy 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

Substituents

3',5'-cyclic purine ribonucleotide
Pentose phosphate
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Imidazopyrimidine
Purine
Aminopyrimidine
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Primary aromatic amine
Pyrimidine
Imidolactam
Oxolane
Azole
Imidazole
Heteroaromatic compound
Secondary alcohol
Azacycle
Organoheterocyclic compound
Oxacycle
Primary amine
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Amine
Organooxygen compound
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a nucleoside 3',5'-cyclic phosphate, a purine-related compound (CAMP)

Physical Properties

State:

Solid

Charge:

-1

Melting point:

219 - 220 °C

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 mg/mL	ALOGPS
logP	-2.3	ALOGPS
logP	-3.8	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.83	ChemAxon
pKa (Strongest Basic)	4.99	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	28.22 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Not Available

Reactions:

cyclic-AMP + Water → Hydrogen ion + AMP

Pathways:

Purine Metabolism pae00230

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00di-9761000000-ed8f1fea0ef2e7b43ff8	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-03du-2971000000-c0200940e0e88308fbde	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-0009000000-02ee7f342f5c1bada389	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-0009000000-a00a2165c3d37c4e1ef2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-0109000000-7f48145f84828c2bbd5d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0119000000-d94a34a13521ae3d4692	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0900000000-f10e1d70e30865424af6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03dr-0629000000-bf4ec1094b7991c3633c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03dr-0629000000-9736faaf70ec79d5bd03	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0109000000-6bf3784f4b710ce04a3e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03dr-0629000000-3f5ea9ba1508e359ad80	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03dr-0519000000-059e8569ee179529bf21	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0009000000-88dad10a362b1088849e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0509004000-bb02289fcd39ac1a203c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-1900000000-da49323734f24bf724d6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0900000000-a4e60131f41413b6fecf	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0009000000-98ee4e70689c06adc603	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-056r-0409005001-97fd793d1d14a84c3530	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0900000000-1f2045ac2ff736aa80a2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0900000000-8bbb24702fa6ccd76268	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0009000000-6d23df7535894180e6df	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001i-0009000000-c527aad341e122fc9bea	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-001i-0209000000-1bb2d660cc00c85a808f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-003r-2904000000-865c1b989665f73ac3f4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

References

References:

Butt E, Beltman J, Becker DE, Jensen GS, Rybalkin SD, Jastorff B, Beavo JA (1995)Characterization of cyclic nucleotide phosphodiesterases with cyclic AMP analogs: topology of the catalytic sites and comparison with other cyclic AMP-binding proteins. Molecular pharmacology 47, Pubmed: 7870042
Beltman J, Becker DE, Butt E, Jensen GS, Rybalkin SD, Jastorff B, Beavo JA (1995)Characterization of cyclic nucleotide phosphodiesterases with cyclic GMP analogs: topology of the catalytic domains. Molecular pharmacology 47, Pubmed: 7870041

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)

Links

External Links:

Resource	Link
CAS	60-92-4
ChEBI	58165
ChemSpider	5415746
HMDB	HMDB00058
IAF1260	1484809
KEGG	C00575
MetaboLights	MTBLC58165
PubChem	7059571

cyclic-AMP (PAMDB110476)

Structure for cyclic-AMP (PAMDB110476)