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

• ChemBase ID: 155542
• Molecular Formular: C14H26N6O14P2
• Molecular Mass: 564.335562
• Monoisotopic Mass: 564.0982228
• 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.C(C(CO)(CO)N)O
• 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.OCC(CO)(CO)N
• InChI: InChI=1S/C10H15N5O11P2.C4H11NO3/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;5-4(1-6,2-7)3-8/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H2,19,20,21)(H3,11,13,14,18);6-8H,1-3,5H2/t3-,5-,6-,9-;/m1./s1
• InChIKey: YWMHXINREUQYRO-GWTDSMLYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-2-(hydroxymethyl)propane-1,3-diol; [({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
• IUPAC Traditional name: GDP; tris buffer
• Synonyms: GDP; Guanosine 5′-diphosphate tris salt from Saccharomyces cerevisiae

Database IDs

• CAS Number: 103192-39-8
• MDL Number: MFCD00058344
• PubChem SID: 162249680
• PubChem CID: 71312154

CALCULATED PROPERTIES

• Acid pKa: 1.9690444
• H Acceptors: 12
• H Donor: 7
• LogD (pH = 5.5): -7.630379
• LogD (pH = 7.4): -8.285877
• Log P: -3.463729
• Molar Refractivity: 86.3669 cm^3
• Polarizability: 33.722054 Å^3
• Polar Surface Area: 248.28 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

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: ~95%
• Type: Type VI
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C10H15N5O11P2

DETAILS

Sigma Aldrich - G7252

Biochem/physiol Actions
Guanosine 5′-diphosphate (GDP) is the diphosphate nucleoside of the purine guanine. GDP and GTP are involved in and may be used to study cell signaling via G-coupled protein receptors (GCPR) and guanine nucleotide exchange factors (GEF) and a variety of GTPases.