[({[(2S,3R,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-4-hydroxy-3-{[hydroxy(phosphonooxy)phosphoryl]oxy}oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid

• ChemBase ID: 3651
• Molecular Formular: C10H17N5O17P4
• Molecular Mass: 603.160324
• Monoisotopic Mass: 602.95699063
• SMILES: Nc1nc2c(ncn2[C@@H]2O[C@@H](CO[P@@](=O)(O)OP(=O)(O)O)[C@H](O[P@@](=O)(O)OP(=O)(O)O)[C@H]2O)c(=O)[nH]1
• Canonical SMILES: O[C@@H]1[C@@H](O[P@](=O)(OP(=O)(O)O)O)[C@@H](O[C@H]1n1cnc2c1nc(N)[nH]c2=O)CO[P@](=O)(OP(=O)(O)O)O
• InChI: InChI=1S/C10H17N5O17P4/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6(30-36(26,27)32-34(21,22)23)3(29-9)1-28-35(24,25)31-33(18,19)20/h2-3,5-6,9,16H,1H2,(H,24,25)(H,26,27)(H2,18,19,20)(H2,21,22,23)(H3,11,13,14,17)/t3-,5+,6-,9+/m0/s1
• InChIKey: BUFLLCUFNHESEH-FULWYAMNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [({[(2S,3R,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-4-hydroxy-3-{[hydroxy(phosphonooxy)phosphoryl]oxy}oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
• IUPAC Traditional name: @guanosine-5',3'-tetraphosphate
• Synonyms: Guanosine-5',3'-Tetraphosphate

Database IDs

• PubChem SID: 160967089; 46508997
• PubChem CID: 46936862

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.0875807
• H Acceptors: 16
• H Donor: 9
• LogD (pH = 5.5): -12.6228695
• LogD (pH = 7.4): -13.886048
• Log P: -3.9820416
• Molar Refractivity: 108.1127 cm^3
• Polarizability: 43.211178 Å^3
• Polar Surface Area: 341.34 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.29
• LOG S: -1.85
• Solubility (Water): 8.42e+00 g/l

DETAILS

DrugBank - DB04022

• Drug Groups: experimental
• Description: Guanosine 5'-diphosphate 2'(3')-diphosphate. A guanine nucleotide containing four phosphate groups. Two phosphate groups are esterified to the sugar moiety in the 5' position and the other two in the 2' or 3' position. This nucleotide serves as a messenger to turn off the synthesis of ribosomal RNA when amino acids are not available for protein synthesis. Synonym: magic spot I. [PubChem]