[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid; bis(cyclohexanamine)

• ChemBase ID: 155525
• Molecular Formular: C22H41N7O10P2
• Molecular Mass: 625.549362
• Monoisotopic Mass: 625.23901381
• SMILES: c1nc(c2c(n1)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)(O)OP(=O)(O)O)O)O)N.C1CCC(CC1)N.C1CCC(CC1)N
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(O)O)O)O[C@H]([C@@H]1O)n1cnc2c1ncnc2N.NC1CCCCC1.NC1CCCCC1
• InChI: InChI=1S/C10H15N5O10P2.2C6H13N/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20;2*7-6-4-2-1-3-5-6/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20);2*6H,1-5,7H2/t4-,6-,7-,10-;;/m1../s1
• InChIKey: SCOUEIPNDLFPCX-IDIVVRGQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid; bis(cyclohexanamine)
• IUPAC Traditional name: bis(cyclohexylamine) adenosine-diphosphate
• Synonyms: ADP; Adenosine 5′-diphosphate bis(cyclohexylammonium) salt; 腺苷-5′-二磷酸 双环己铵盐

Database IDs

• CAS Number: 102029-87-8
• MDL Number: MFCD00058338
• PubChem SID: 162249663
• PubChem CID: 71312150

CALCULATED PROPERTIES

• Acid pKa: 1.7714787
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -7.1348915
• LogD (pH = 7.4): -7.671735
• Log P: -4.982523
• Molar Refractivity: 84.9414 cm^3
• Polarizability: 33.853855 Å^3
• Polar Surface Area: 232.6 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble, clear to slightly hazy, colorless to faintly yellow
• Apperance: crystalline

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% (HPLC)
• Biological Source: bacterial
• Empirical Formula (Hill Notation): C10H15N5O10P2 · 2C6H13N

DETAILS

Sigma Aldrich - A4386

Caution
Stable, non-hygroscopic
Application
Adenosine 5′-diphosphate (ADP) is an adenine nucleotide involved in energy storage and nucleic acid metabolism via its conversion into ATP by ATP synthases. ADP affects platelet activation through its interaction with ADP receptors P2Y1, P2Y12 and P2X1. Upon its conversion to adenosine by ecto-ADPases, platelet activation is inhibited via adenosine receptors.