Livestock Metabolome Database: Showing metabocard for Cyclic AMP (LMDB00025)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:40:43 UTC

Update Date

2016-07-19 23:37:36 UTC

Lmdb

LMDB00025

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cyclic AMP

Description

Cyclic AMP, also known as CAMP or cyclic adenylate, 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. cAMP decomposition into AMP is catalyzed by the enzyme phosphodiesterase. It is a second messenger and a key intracellular regulator, functioning as a mediator of activity for a number of hormones, including epinephrine, glucagon, and ACTH. 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). Cyclic AMP is a strong basic compound (based on its pKa). Cyclic AMP exists in all living species, ranging from bacteria to humans. cAMP is synthesized from ATP by adenylate cyclase. In humans, cyclic AMP is involved in intracellular signalling through adenosine receptor A2A and adenosine. Outside of the human body, Cyclic AMP has been detected, but not quantified in, several different foods, such as cherry tomato, cascade huckleberries, black chokeberries, ryes, and common wheats. This could make cyclic AMP a potential biomarker for the consumption of these foods. Cyclic AMP is an adenine nucleotide containing one phosphate group which is esterified to both the 3'- and 5'-positions of the sugar moiety. Liver adenylate cyclase responds more strongly to glucagon, and muscle adenylate cyclase responds more strongly to adrenaline. Adenylate cyclase is located at the cell membranes. Adenylate cyclase is activated by the hormones glucagon and adrenaline and by G protein.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Adenosine 3',5'-cyclic monophosphate	ChEBI
Adenosine 3',5'-cyclic phosphate	ChEBI
Adenosine 3',5'-phosphate	ChEBI
ADENOSINE-3',5'-cyclic-monophosphATE	ChEBI
CAMP	ChEBI
Cyclic adenylic acid	ChEBI
Adenosine 3',5'-cyclic monophosphoric acid	Generator
Adenosine 3',5'-cyclic phosphoric acid	Generator
Adenosine 3',5'-phosphoric acid	Generator
ADENOSINE-3',5'-cyclic-monophosphoric acid	Generator
Cyclic adenylate	Generator
3'5'-Cyclic AMP	HMDB
6-(6-Amino-9H-purin-9-yl)tetrahydro-4H-furo[3,2-D][1,3,2]dioxaphosphinine-2,7-diol 2-oxide	HMDB
Acrasin	HMDB
Adenosine 3',5'-cyclophosphate	HMDB
Adenosine 3',5'-monophosphate	HMDB
Adenosine 3,5'-cyclic monophosphorate	HMDB
Adenosine 3,5'-cyclic monophosphoric acid	HMDB
Adenosine cyclic monophosphate	HMDB
Adenosine cyclic-monophosphate	HMDB
Adenosine-cyclic-phosphate	HMDB
Adenosine-cyclic-phosphoric-acid	HMDB
Cyclic 3',5'-adenylate	HMDB
Cyclic 3',5'-adenylic acid	HMDB
Cyclic 3',5'-AMP	HMDB
Cyclic adenosine 3',5'-phosphate	HMDB
3',5'-monoPhosphate, adenosine cyclic	HMDB
Cyclic AMP, disodium salt	HMDB
Cyclic AMP, monopotassium salt	HMDB
Cyclic AMP, sodium salt	HMDB
AMP, Cyclic	HMDB
Adenosine cyclic 3',5' monophosphate	HMDB
Adenosine cyclic-3',5'-monophosphate	HMDB
Cyclic AMP, (R)-isomer	HMDB
Cyclic AMP, monosodium salt	HMDB
Adenosine cyclic 3',5'-monophosphate	HMDB
monoPhosphate, adenosine cyclic	HMDB
Adenosine cyclic 3,5 monophosphate	HMDB
Cyclic 3',5'-monophosphate, adenosine	HMDB
Cyclic AMP, monoammonium salt	HMDB
Cyclic monophosphate, adenosine	HMDB
Cyclic-3',5'-monophosphate, adenosine	HMDB
Cyclic AMP	ChEBI

Chemical Formula

C₁₀H₁₂N₅O₆P

Average Molecular Weight

329.2059

Monoisotopic Molecular Weight

329.052519653

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

Traditional Name

(4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2,7-dihydroxy-tetrahydro-4H-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-2-one

CAS Registry Number

60-92-4

SMILES

NC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H]2COP(O)(=O)O[C@H]2[C@H]1O

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

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

3',5'-cyclic purine nucleotide (CHEBI:17489 )
adenyl ribonucleotide (CHEBI:17489 )
3',5'-Cyclic nuclcleotides (C00575 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.3	ALOGPS
logP	-3.4	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.83	ChemAxon
pKa (Strongest Basic)	3.92	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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00di-9761000000-ed8f1fea0ef2e7b43ff8	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-03du-2971000000-c0200940e0e88308fbde	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9761000000-ed8f1fea0ef2e7b43ff8	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-03du-2971000000-c0200940e0e88308fbde	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fbl-3901000000-b95501fad426dc61082f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-03y0-3922000000-7e84eb99b8248254daa6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-0009000000-02ee7f342f5c1bada389	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-0009000000-a00a2165c3d37c4e1ef2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-0109000000-7f48145f84828c2bbd5d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0119000000-d94a34a13521ae3d4692	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0900000000-f10e1d70e30865424af6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03dr-0629000000-bf4ec1094b7991c3633c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03dr-0629000000-9736faaf70ec79d5bd03	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0109000000-6bf3784f4b710ce04a3e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03dr-0629000000-3f5ea9ba1508e359ad80	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03dr-0519000000-059e8569ee179529bf21	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-0009000000-88dad10a362b1088849e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0509004000-bb02289fcd39ac1a203c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-1900000000-da49323734f24bf724d6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0900000000-a4e60131f41413b6fecf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0009000000-98ee4e70689c06adc603	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-056r-0409005001-97fd793d1d14a84c3530	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0900000000-1f2045ac2ff736aa80a2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-001i-0900000000-8bbb24702fa6ccd76268	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0009000000-6d23df7535894180e6df	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001i-0009000000-c527aad341e122fc9bea	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-001i-0209000000-1bb2d660cc00c85a808f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-003r-2904000000-865c1b989665f73ac3f4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0904000000-f37dad1d4334840eb74e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-8b2624b0c421f5f77e8e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900000000-3052962b6de42b1e2f5d	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum