cGMP (C10H12N5O7P): structure, properties and hazards

Names and identifiers

IUPAC name: 9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-1H-purin-6-one
Synonyms: cyclic GMP, second messenger, cyclic gmp
+ 37 more
Cyclic guanosine monophosphate, 3',5'-cyclic GMP, Guanosine 3',5'-cyclic monophosphate, Guanosine cyclic monophosphate, guanosine 3',5'-cyclic phosphate, Guanosine 3',5'-phosphate, H2D2X058MU, DTXSID8040646, CHEBI:16356, Guanosine, cyclic 3',5'-(hydrogen phosphate), Guanosine cyclic 3',5'-monophosphate, cyclic 3',5'-guanosine monophosphate, 9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-1H-purin-6-one, GMP, Cyclic, 9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-3H-purin-6-one, 9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-hexahydro-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-6,9-dihydro-1H-purin-6-one, Cyclic Monophosphate, Guanosine, Monophosphate, Guanosine Cyclic, 2-amino-9-((1S,6R,8R,9R)-3,9-dihydroxy-3-oxo-2,4,7-trioxa-3$l^(5)-phosphabicyclo(4.3.0)nonan-8-yl)-3H-purin-6-one, 2-amino-9-[(1S,6R,8R,9R)-3,9-dihydroxy-3-oxo-2,4,7-trioxa-3$l^{5}-phosphabicyclo[4.3.0]nonan-8-yl]-3H-purin-6-one, 9-((4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo(3,2-d)(1,3,2)dioxaphosphinin-6-yl)-2-amino-1H-purin-6-one, 9-((4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo(3,2-d)(1,3,2)dioxaphosphinin-6-yl)-2-amino-3H-purin-6-one, 9-((4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-hexahydro-1,3,5,2$l^(5)-furo(3,2-d)(1,3,2$l^(5))dioxaphosphinin-6-yl)-2-amino-6,9-dihydro-1H-purin-6-one, 9-((4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-hexahydro-2lambda5-furo(3,2-d)(1,3,2)dioxaphosphinin-6-yl)-2-amino-6,9-dihydro-1H-purin-6-one, 9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-hexahydro-1,3,5,2$l^{5}-furo[3,2-d][1,3,2$l^{5}]dioxaphosphinin-6-yl]-2-amino-6,9-dihydro-1H-purin-6-one, Guanosine Cyclic 3,5 Monophosphate, Guanosine Cyclic 3',5' Monophosphate, Guanosine Cyclic-3',5'-Monophosphate, 3',5'-Monophosphate, Guanosine Cyclic, Cyclic 3',5'-Monophosphate, Guanosine, Cyclic-3',5'-Monophosphate, Guanosine, RefChem:34252, DTXCID6020646, 231-641-6, Guanosine 3',5'-monophosphate, Cyclic 3',5'-GMP, cyclic-GMP
Molecular formula: C₁₀H₁₂N₅O₇P
Empirical formula: C₁₀H₁₂N₅O₇P
Molecular weight: 345.21 g/mol
Exact mass: 345.04743
CAS number: 7665-99-8
PubChem CID: 135398570
Canonical SMILES: C1C2C(C(C(O2)N3C=NC4=C3N=C(NC4=O)N)O)OP(=O)(O1)O
Isomeric SMILES: C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C3N=C(NC4=O)N)O)OP(=O)(O1)O
InChI: InChI=1S/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1
InChIKey: ZOOGRGPOEVQQDX-UUOKFMHZSA-N
Molfile

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

Calculated

Heavy atoms: 23
Rings: 4
Aromatic rings: 2
Fraction sp³ carbons (Fsp3): 0.5
H-bond donors: 4
H-bond acceptors: 9
Rotatable bonds: 1
TPSA (Å²): 174.8 computed here · PubChem 171
Formal charge: 0
XLogP3: -3.4 PubChem
Complexity: 616 PubChem
Stereocenters: 4 defined, 1 undefinedCIP: C9: R · C11: R · P14: undefined · C18: S · C19: 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

C34.79%
H3.50%
N20.29%
O32.44%
P8.97%

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: -1.52 Crippen (Wildman and Crippen 1999)
log S (water solubility): -1.24 ESOL (Delaney 2004), log mol/L
Synthetic accessibility: 4.5 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

Molecular weight ≤ 500: 345.21
log P ≤ 5 (Crippen): -1.52
H-bond donors ≤ 5: 4
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

Warning

Most widely reported: 40 company reports to ECHA. Source [1].

Harmful or irritant

H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation

Precautionary statements: P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501

Safety data sheets on the supplier’s page: ChemoSapiens, Alfa Chemistry, AA BLOCKS.

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]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
[4]MassBank Europe · 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.

Similar structures

Tanimoto similarity on Morgan fingerprints (radius 2) with RDKit 2026.09, at least 45%.