guanosine 5'-monophosphate (GMP)

ID: ALA1242996

Chembl Id: CHEMBL1242996

PubChem CID: 135887992

Max Phase: Preclinical

Molecular Formula: C10H14N5O8P

Molecular Weight: 363.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc2c(ncn2[C@@H]2O[C@H](COP(=O)(O)O)[C@H](O)[C@@H]2O)c(=O)[nH]1

Standard InChI:  InChI=1S/C10H14N5O8P/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,16-17H,1H2,(H2,19,20,21)(H3,11,13,14,18)/t3-,5+,6+,9-/m1/s1

Standard InChI Key:  RQFCJASXJCIDSX-GFRUICAKSA-N

Alternative Forms

1. Parent:

   

   ALA1242996

   E626

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 363.22

Molecular Weight (Monoisotopic): 363.0580

AlogP: -2.57

#Rotatable Bonds: 4

Polar Surface Area: 206.04

Molecular Species: ACID

HBA: 10

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.22

CX Basic pKa: 0.38

CX LogP: -3.12

CX LogD: -6.36

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.31

Np Likeness Score: 1.25

References

1. Kim CU, Luh BY, Misco PF, Bronson JJ, Hitchcock MJ, Ghazzouli I, Martin JC..  (1990)  Acyclic purine phosphonate analogues as antiviral agents. Synthesis and structure-activity relationships.,  33  (4): [PMID:2157012] [10.1021/jm00166a019]

2. Raju N, Smee DF, Robins RK, Vaghefi MM..  (1989)  Synthesis and biological properties of purine and pyrimidine 5'-deoxy-5'-(dihydroxyphosphinyl)-beta-D-ribofuranosyl analogues of AMP, GMP, IMP, and CMP.,  32  (6): [PMID:2542559] [10.1021/jm00126a027]

3. Nave J, Casara PJ, Taylor DL, Stanley Tyms A, Kenny M, HalazyS S.  (1996)  Synthesis, enzymatic phosphorylation and antiviral activity of acyclic dienyl phosphonate derivatives of guanine,  6  (2): [10.1016/0960-894X(95)00585-H]

4. Wong CG, Meyer RB..  (1984)  Inhibitors of inosinic acid dehydrogenase. 2-Substituted inosinic acids.,  27  (4): [PMID:6142953] [10.1021/jm00370a003]

5. Bai G, Feng B, Wang JB, Pozharski E, Shapiro M..  (2010)  Studies on ligand binding to histidine triad nucleotide binding protein 1.,  18  (18): [PMID:20724166] [10.1016/j.bmc.2010.07.051]

Source

Source(1):

• Scientific Literature