9-[(4aR,6S,7S,7aR)-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

• ChemBase ID: 2060
• Molecular Formular: C10H12N5O7P
• Molecular Mass: 345.205341
• Monoisotopic Mass: 345.04743438
• SMILES: Nc1nc2c(ncn2[C@H]2O[C@@H]3CO[P@@](=O)(O)O[C@@H]3[C@@H]2O)c(=O)[nH]1
• Canonical SMILES: O[C@H]1[C@H]2O[P@](=O)(O)OC[C@H]2O[C@@H]1n1cnc2c1nc(N)[nH]c2=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-KHLHZJAASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-[(4aR,6S,7S,7aR)-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
• IUPAC Traditional name: @guanosine-3',5'-monophosphate
• Synonyms: Cyclic Guanosine Monophosphate; Guanosine-3',5'-Monophosphate

Database IDs

• CAS Number: 7665-99-8
• PubChem SID: 46508914; 160965514
• PubChem CID: 46936347

CALCULATED PROPERTIES

JChem

• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -4.2590003
• LogD (pH = 7.4): -4.309573
• Log P: -2.0959094
• Molar Refractivity: 71.715 cm^3
• Polarizability: 27.73993 Å^3
• Polar Surface Area: 170.52 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true
• Acid pKa: 2.0500584

ALOGPS 2.1

• Log P: -1.98
• LOG S: -1.96
• Solubility (Water): 3.79e+00 g/l

DETAILS

DrugBank - DB02315

• Drug Groups: experimental
• Description: A guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger. Its levels increase in response to a variety of hormones, including acetylcholine, insulin, and oxytocin and it has been found to activate specific protein kinases. (From Merck Index, 11th ed)

DrugBank - DB04536

Drug information: experimental