(2S)-2-amino-1-[({[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}sulfonyl)amino]-3-(4-hydroxyphenyl)propan-1-one

• ChemBase ID: 3014
• Molecular Formular: C19H23N7O8S
• Molecular Mass: 509.49302
• Monoisotopic Mass: 509.13288173
• SMILES: N[C@@H](Cc1ccc(O)cc1)C(=O)NS(=O)(=O)OC[C@@H]1O[C@H]([C@H](O)[C@H]1O)n1cnc2c1ncnc2N
• Canonical SMILES: O=C([C@H](Cc1ccc(cc1)O)N)NS(=O)(=O)OC[C@@H]1O[C@H]([C@@H]([C@H]1O)O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C19H23N7O8S/c20-11(5-9-1-3-10(27)4-2-9)18(30)25-35(31,32)33-6-12-14(28)15(29)19(34-12)26-8-24-13-16(21)22-7-23-17(13)26/h1-4,7-8,11-12,14-15,19,27-29H,5-6,20H2,(H,25,30)(H2,21,22,23)/t11-,12-,14-,15+,19+/m0/s1
• InChIKey: MJZAZMKENKZBAJ-NEYKFGMSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-1-[({[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}sulfonyl)amino]-3-(4-hydroxyphenyl)propan-1-one
• IUPAC Traditional name: @tyrosyladenylate
• Synonyms: Tyrosyladenylate

Database IDs

• PubChem SID: 46507246; 160966461
• PubChem CID: 46936642

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.4374876
• H Acceptors: 13
• H Donor: 6
• LogD (pH = 5.5): -2.653672
• LogD (pH = 7.4): -2.5667076
• Log P: -2.5706134
• Molar Refractivity: 118.7422 cm^3
• Polarizability: 47.35498 Å^3
• Polar Surface Area: 238.03 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.71
• LOG S: -2.37
• Solubility (Water): 2.15e+00 g/l

DETAILS

DrugBank - DB03325

Drug information: experimental