9-[(3aR,4R,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2H-1,3,5,2λ5-furo[3,4-d][1,3,2λ5]dioxaphosphol-4-yl]-2-amino-6,9-dihydro-3H-purin-6-one; triethylamine

• ChemBase ID: 169803
• Molecular Formular: C16H27N6O7P
• Molecular Mass: 446.395341
• Monoisotopic Mass: 446.16788386
• SMILES: N(CC)(CC)CC.n1c([nH]c2c(c1=O)ncn2[C@H]1[C@H]2[C@@H]([C@H](O1)CO)OP(=O)(O2)O)N
• Canonical SMILES: OC[C@H]1O[C@H]([C@H]2[C@@H]1OP(=O)(O2)O)n1cnc2c1[nH]c(N)nc2=O.CCN(CC)CC
• InChI: InChI=1S/C10H12N5O7P.C6H15N/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-6-5(3(1-16)20-9)21-23(18,19)22-6;1-4-7(5-2)6-3/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17);4-6H2,1-3H3/t3-,5-,6-,9-;/m1./s1
• InChIKey: XSJQZRFQUIJXDC-GWTDSMLYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-[(3aR,4R,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2H-1,3,5,2λ^5-furo[3,4-d][1,3,2λ^5]dioxaphosphol-4-yl]-2-amino-6,9-dihydro-3H-purin-6-one; triethylamine
• IUPAC Traditional name: 9-[(3aR,4R,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-1,3,5,2λ^5-furo[3,4-d][1,3,2λ^5]dioxaphosphol-4-yl]-2-amino-3H-purin-6-one; triethylamine
• Synonyms: Guanosine Cyclic 2',3'-(Hydrogen Phosphate) N,N-Diethylethanamine; Guanosine 2',3'-Cyclic Monophosphate Triethylamine Salt

Database IDs

• CAS Number: 73647-09-3
• PubChem SID: 162263935
• PubChem CID: 71317171

CALCULATED PROPERTIES

• Acid pKa: 1.6988643
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -3.7750611
• LogD (pH = 7.4): -3.8873322
• Log P: -2.3971205
• Molar Refractivity: 71.2816 cm^3
• Polarizability: 27.919397 Å^3
• Polar Surface Area: 170.52 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - G837950

A cyclic nucleotide with non-selective neoplasm inhibitory effects. It inhibited the growth of 4 tumorigenic cell lines, strain L, HeLa, HEp-2, and F1 amnion as well as nonmalignant cell lines. It also has analgesic activity.

REFERENCES

• Heldrick, M.L. et al.: Cancer Res., 30, 376 (1970)
• Vocci, F.J. et al.: J. Pharmacol. Exp. Therap., 207, 892 (1970)