(2S,3S,4S,5R,6S)-6-({5-[(2E)-5-carboxy-3-methylpent-2-en-1-yl]-6-(2H3)methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 174875
• Molecular Formular: C23H28O12
• Molecular Mass: 496.46122
• Monoisotopic Mass: 496.15807634
• SMILES: c1(c(c(c2c(c1O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O)C(=O)OC2)C)OC)C/C=C(/CCC(=O)O)\C
• Canonical SMILES: COc1c(C/C=C(/CCC(=O)O)\C)c(O[C@@H]2O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]2O)O)O)c2c(c1C)COC2=O
• InChI: InChI=1S/C23H28O12/c1-9(5-7-13(24)25)4-6-11-18(32-3)10(2)12-8-33-22(31)14(12)19(11)34-23-17(28)15(26)16(27)20(35-23)21(29)30/h4,15-17,20,23,26-28H,5-8H2,1-3H3,(H,24,25)(H,29,30)/b9-4+/t15-,16-,17+,20-,23+/m0/s1
• InChIKey: BYFGTSAYQQIUCN-HGIHDBQLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-({5-[(2E)-5-carboxy-3-methylpent-2-en-1-yl]-6-(^2H₃)methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-({5-[(2E)-5-carboxy-3-methylpent-2-en-1-yl]-6-(^2H₃)methoxy-7-methyl-3-oxo-1H-2-benzofuran-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 5-[(2E)-5-Carboxy-3-methyl-2-penten-1-yl]-1,3-dihydro-6-(methoxy-d3)-7-methyl-3-oxo-4-isobenzofuranyl β-D-Glucopyranosiduronic Acid; Mycophenolic Acid-d3 Glucosiduronate; Mycophenolic Acid-d3 Glucuronide; Mycophenolic Acid-d3 β-D-Glucuronide

Database IDs

• PubChem SID: 164230785
• PubChem CID: 71750872

CALCULATED PROPERTIES

• Acid pKa: 2.739151
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -3.6937711
• LogD (pH = 7.4): -5.941499
• Log P: 0.9298039
• Molar Refractivity: 117.2452 cm^3
• Polarizability: 45.85586 Å^3
• Polar Surface Area: 189.28 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 155-159°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M831522

A labelled metabolite of Mycophenolic Acid, an antibiotic produced by Penicillium brevi-compactum, P. Stoloniferum and related spp. A selective inhibitor of lymphocyte proliferation by blocking inosine monophosphate dehydrogenase, an enzyme involved in t

REFERENCES

• Senda, M., et al.: Transplantation, 60, 1143 (1995)
• Nimmesgern, E., et al.: J. Biol. Chem., 271, 19421 (1995)
• Gummert, J.F., et al.: J. Pharmacol. Exp. Ther., 291, 1100 (1995)