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

• ChemBase ID: 2613
• Molecular Formular: C10H15N5O13P2S
• Molecular Mass: 507.264322
• Monoisotopic Mass: 506.98622983
• SMILES: Nc1ncnc2c1ncn2[C@@H]1O[C@@H](CO[P@@](=O)(O)OS(=O)(=O)O)[C@H](OP(=O)(O)O)[C@H]1O
• Canonical SMILES: O[C@@H]1[C@@H](OP(=O)(O)O)[C@@H](O[C@H]1n1cnc2c1ncnc2N)CO[P@](=O)(OS(=O)(=O)O)O
• InChI: InChI=1S/C10H15N5O13P2S/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(27-29(17,18)19)4(26-10)1-25-30(20,21)28-31(22,23)24/h2-4,6-7,10,16H,1H2,(H,20,21)(H2,11,12,13)(H2,17,18,19)(H,22,23,24)/t4-,6+,7-,10+/m0/s1
• InChIKey: GACDQMDRPRGCTN-PERBPWGJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [({[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]sulfonic acid
• IUPAC Traditional name: {[(2S,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxysulfonic acid
• Synonyms: 3'-Phosphate-Adenosine-5'-Phosphate Sulfate

Database IDs

• PubChem SID: 46508242; 160966062
• PubChem CID: 46936522

CALCULATED PROPERTIES

JChem

• Acid pKa: -2.0784824
• H Acceptors: 14
• H Donor: 6
• LogD (pH = 5.5): -9.7927065
• LogD (pH = 7.4): -11.174554
• Log P: -7.1075835
• Molar Refractivity: 94.9332 cm^3
• Polarizability: 38.881847 Å^3
• Polar Surface Area: 275.97 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.65
• LOG S: -2.0
• Solubility (Water): 5.05e+00 g/l

DETAILS

DrugBank - DB02902

• Drug Groups: experimental
• Description: 3'-Phosphoadenosine-5'-phosphosulfate. Key intermediate in the formation by living cells of sulfate esters of phenols, alcohols, steroids, sulfated polysaccharides, and simple esters, such as choline sulfate. It is formed from sulfate ion and ATP in a two-step process. This compound also is an important step in the process of sulfur fixation in plants and microorganisms. [PubChem]