Camp
Completing data — refresh the page later to see the latest
Basic information
- CAS
60-92-4- Standard SMILES
Nc1ncnc2c1ncn2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O- InChIKey
IVOMOUWHDPKRLL-KQYNXXCUSA-N- Molecular formula
- C10H12N5O6P
- Average molar mass
- 329.21 g/mol
- Monoisotopic mass
- 329.05251973
Overview
3',5'-cyclic AMP is a 3',5'-cyclic purine nucleotide having having adenine as the nucleobase. It has a role as a mouse metabolite, an Escherichia coli metabolite and a human metabolite. It is a 3',5'-cyclic purine nucleotide and an adenyl ribonucleotide. It is a conjugate acid of a 3',5'-cyclic AMP(1-).
Names & identifiers
- Preferred name
- Camp
- IUPAC
- (4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
- English name
- Cyclic AMP
- Molecular formula
- C10H12N5O6P
- Molecular weight
- 329.21
Names & synonyms
Cyclic AMPcAMP60-92-4Adenosine 3',5'-cyclic monophosphate3',5'-cyclic AMPAdenosine 3',5'-cyclophosphatecyclic 3',5'-AMPAdenosine 3',5'-phosphateCyclic Adenosine MonophosphateAdenosine cyclic monophosphatecyclic 3',5'-Adenylic acidAdenosine 3',5'-monophosphate
Show more names
ADENOSINE CYCLOPHOSPHATEAcrasinADENOSINE CYCLPHOSPHATE(4aR,6R,7R,7aS)-6-(6-Amino-9H-purin-9-yl)-2,7-dihydroxytetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinine 2-oxideMRD40C13orf83:5-CAMPKIAA1802
cyclic Adenosine 3',5'-phosphateAdenosine cyclic 3',5'-monophosphateAdenosine, cyclic 3',5'-(hydrogen phosphate)Adenosine 3',5'-cyclic phosphate3',5'-AMPAdenosine cyclic 3',5'-phosphateAdenosine cyclic phosphateCyclic adenylic acid
Database identifiers
Properties
Computed structural propertiesFilling in
- XLogP
- -2.6
- Topological polar surface area
- 155 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 1
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 498
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsSkin conditioning
LogP-2.96
Solubility4 mg/mL
Melting Point
219-220 °C
219 - 220 °C
Physical DescriptionSolid
Collision Cross Section
176.8 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
172 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]
175.07 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
188.8 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
181.3 Ų [M+Na]+
Physicochemical properties
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 33.3% (2 of 6) of reports.
Danger
H314 (16.7%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
P260, P261, P264, P264+P265, P271, P280, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P332+P317, P337+P317, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 6 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Adenosine, cyclic 3',5'-(hydrogen phosphate)
Adenosine, cyclic 3',5'-(hydrogen phosphate): Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationIMAP assessments - Adenosine, cyclic 3',5'-(hydrogen phosphate): Environment tier I assessment
Hazard Classes and CategoriesSkin Corr. 1B (16.7%)
Safety data
- F
- 10-21
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- AU7357600
- hs_code
- 29349990
- Toxicity
- oms-hmn:oth 100 mmol/L JIDEAE 65,52,75
Chemistry & industry
Pharmacology
Tissue LocationsAll Tissues
Cellular LocationsCytoplasm
Metabolite PathwaysAdenine phosphoribosyltransferase deficiency (APRT)
Uses & manufacturing
Household ProductsInformation on 1 consumer products that contain cyclic AMP (adenosine cyclic phosphate) in the following categories is provided:
Use ClassificationCosmetics -> Skin conditioning
General Manufacturing InformationAdenosine, cyclic 3',5'-(hydrogen phosphate): ACTIVE
Applications
UsescAMP is used for intracellular signal transduction in many different organisms, conveying the cAMP-dependent pathway. Restoration of several morphological characteristics of normal fibroblasts in sarcoma cells when treated with adenosine-3': 5'-cyclic monophosphate. In the presence of adenosine 3':5'-cyclic monophosphate, protein kinase I dissociated into two subunits: a subunit binding adenosine 3':5'-cyclic monophosphate, and a catalytic subunit. Stimulation of calcium uptake in platelet membrane vesicles by adenosine 3',5'-cyclic monophosphate.
General DescriptionCyclic AMP is a second messenger molecule comprised of an adenine ribonucleotide bearing a phosphate group bound to the oxygen molecules at the 3' and 5' positions of the sugar moiety. Cyclic AMP, which is synthesized from ATP by the intracellular enzyme adenylate cyclase, modulates the activity of several hormone-dependent signal transduction pathways.
Upstream & downstream products
Related reactions
19 records
Compound notes
Loading…