cAMP

Athanor · official

C₁₀H₁₂N₅O₆P · 329.21 g/mol

IUPAC name: (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

Also called cyclic AMP, adenosine 3',5'-cyclic monophosphate, second messenger

Nucleic acid parts

Open in Athanor

Drawn from its SMILES with RDKit

DangerCauses severe skin burns and eye damage · Causes skin irritation · Causes serious eye damage · Causes serious eye irritation · May cause respiratory irritation

Names and identifiers

IUPAC name: (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
Synonyms: cyclic AMP, adenosine 3',5'-cyclic monophosphate, second messenger
+ 38 more
Cyclic AMP, Adenosine 3',5'-cyclic monophosphate, 3',5'-cyclic AMP, Adenosine 3',5'-cyclophosphate, cyclic 3',5'-AMP, Adenosine 3',5'-phosphate, Cyclic Adenosine Monophosphate, Adenosine cyclic monophosphate, cyclic 3',5'-Adenylic acid, Adenosine 3',5'-monophosphate, cyclic Adenosine 3',5'-phosphate, Adenosine cyclic 3',5'-monophosphate, Adenosine, cyclic 3',5'-(hydrogen phosphate), Adenosine 3',5'-cyclic phosphate, 3',5'-AMP, Adenosine cyclic 3',5'-phosphate, Adenosine cyclic phosphate, Cyclic adenylic acid, DTXSID8040436, Cyclic Monophosphate, Adenosine, E0399OZS9N, (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, CHEBI:17489, Adenosine Cyclic 3',5' Monophosphate, DTXCID6020436, NSC-143670, Adenosine cyclic 3',5'-(hydrogen phosphate), adenosine cyclic-3',5'-monophosphate, 3',5'-Monophosphate, Adenosine Cyclic, NSC-94017, AMP, Cyclic, (4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-1,3,5,2$l^{5}-furo[3,2-d][1,3,2$l^{5}]dioxaphosphinin-2-one, (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, Monophosphate, Adenosine Cyclic, (1S,6R,8R,9R)-8-(6-aminopurin-9-yl)-3-hydroxy-3-oxo-2,4,7-trioxa-3$l^(5)-phosphabicyclo(4.3.0)nonan-9-ol, (1S,6R,8R,9R)-8-(6-aminopurin-9-yl)-3-hydroxy-3-oxo-2,4,7-trioxa-3$l^{5}-phosphabicyclo[4.3.0]nonan-9-ol, (4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-1,3,5,2$l^(5)-furo(3,2-d)(1,3,2$l^(5))dioxaphosphinin-2-one, (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
Molecular formula: C₁₀H₁₂N₅O₆P
Empirical formula: C₁₀H₁₂N₅O₆P
Molecular weight: 329.21 g/mol
Exact mass: 329.05252
CAS number: 60-92-4
PubChem CID: 6076
Canonical SMILES: C1C2C(C(C(O2)N3C=NC4=C(N=CN=C43)N)O)OP(=O)(O1)O
Isomeric SMILES: C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C(N=CN=C43)N)O)OP(=O)(O1)O
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
InChIKey: IVOMOUWHDPKRLL-KQYNXXCUSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms: 22
Rings: 4
Aromatic rings: 2
Fraction sp³ carbons (Fsp3): 0.5
H-bond donors: 3
H-bond acceptors: 9 computed here · PubChem 10
Rotatable bonds: 1
TPSA (Å²): 154.8 computed here · PubChem 155
Formal charge: 0
XLogP3: -2.6 PubChem
Complexity: 498 PubChem
Stereocenters: 4 defined, 1 undefinedCIP: C11: R · C13: R · P16: undefined · C20: S · C21: R
Double-bond geometry: None specified
Point group: C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

C36.48%
H3.67%
N21.27%
O29.16%
P9.41%

Isotope pattern

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P: -0.82 Crippen (Wildman and Crippen 1999)
log S (water solubility): -1.6 ESOL (Delaney 2004), log mol/L
Synthetic accessibility: 4.35 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

Molecular weight ≤ 500: 329.21
log P ≤ 5 (Crippen): -0.82
H-bond donors ≤ 5: 3
H-bond acceptors ≤ 10: 9

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

Danger

Most widely reported: 6 company reports to ECHA. Source [1].

Corrosive
Harmful or irritant

H314Causes severe skin burns and eye damage (16.7% of reports)
H315Causes skin irritation (50% of reports)
H318Causes serious eye damage (16.7% of reports)
H319Causes serious eye irritation (50% of reports)
H335May cause respiratory irritation (50% of reports)

Precautionary statements: 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, P501

View all classifications (2)

[1] European Chemicals Agency (ECHA)This chemical does not meet GHS hazard criteria for 33.3% (2 of 6) of reports.
[1] European Chemicals Agency (ECHA) · 6 reports · DangerH314, H315, H318, H319, H335

Safety data sheets on the supplier’s page: Alfa Chemistry, SynHet - Synthetic Heterocycles, Angene Chemical.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

[1]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
[2]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
[3]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
[4]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
[5]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
[6]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
·Literature on PubChem

Data last updated 2026-10-14.