disodium [(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl (hydrogen phosphonatooxy)phosphonate

• ChemBase ID: 155887
• Molecular Formular: C10H13N5Na2O11P2
• Molecular Mass: 487.164182
• Monoisotopic Mass: 486.98821808
• SMILES: c1nc2c(=O)[nH]c(nc2n1[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)([O-])OP(=O)(O)[O-])O)O)N.[Na+].[Na+]
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(O)[O-])[O-])O[C@H]([C@@H]1O)n1cnc2c1nc(N)[nH]c2=O.[Na+].[Na+]
• InChI: InChI=1S/C10H15N5O11P2.2Na/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(25-9)1-24-28(22,23)26-27(19,20)21;;/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H2,19,20,21)(H3,11,13,14,18);;/q;2*+1/p-2/t3-,5-,6-,9-;;/m1../s1
• InChIKey: LTZCGDIGAHOTKN-LGVAUZIVSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium [(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl (hydrogen phosphonatooxy)phosphonate
• IUPAC Traditional name: disodium [(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphonatooxyphosphonate
• Synonyms: 5′-GDP-Na2; Guanosine 5′-diphosphate disodium salt

Database IDs

• CAS Number: 7415-69-2
• EC Number: 231-026-2
• MDL Number: MFCD00084665
• PubChem SID: 162250025; 24873516
• PubChem CID: 16213722

CALCULATED PROPERTIES

• Acid pKa: 1.9690444
• H Acceptors: 12
• H Donor: 5
• LogD (pH = 5.5): -7.630379
• LogD (pH = 7.4): -8.285877
• Log P: -3.463729
• Molar Refractivity: 84.1235 cm^3
• Polarizability: 33.482544 Å^3
• Polar Surface Area: 253.94 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL, clear, colorless

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (HPLC)
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C10H13N5Na2O11P2

DETAILS

Sigma Aldrich - 51060

Application
Guanosine 5′-diphosphate (GDP) is used as a substrate of pyruvate kinase to produce GTP in support of RNA biosyntheis. GDP is used to study the kinetics and characteristics of GTPases such as those associated with G-protein coupled receptors (GPCR). GDP is also used to study cell signaling processes mediate by guanine nucleotide exchange factors.