Mycophenolic acid glucuronide

Base Information

• Chemical Name: Mycophenolic acid glucuronide
• CAS No.: 31528-44-6
• Deprecated CAS: 197956-36-8
• Molecular Formula: C₂₃H₂₈O₁₂
• Molecular Weight: 496.468
• Hs Code.: 29389090
• European Community (EC) Number: 803-548-6
• UNII: 54TS5J9T0K
• DSSTox Substance ID: DTXSID401043388
• Nikkaji Number: J1.523.146G
• Mol file: 31528-44-6.mol

Synonyms:MPAG cpd;mycophenolic acid 7-O-glucuronide;mycophenolic acid glucuronide

Chemical Property of Mycophenolic acid glucuronide

Chemical Property:

• Vapor Pressure: 8.48E-33mmHg at 25°C
• Melting Point: 98-100°C
• Boiling Point: 875.7°Cat760mmHg
• PKA: 2.76±0.70(Predicted)
• Flash Point: 299.6°C
• Density: 1.502g/cm³
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 9
• Exact Mass: 496.15807632
• Heavy Atom Count: 35
• Complexity: 827

Purity/Quality:

98%,99%, ^*data from raw suppliers

Mycophenolic acid b-D-glucuronide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36
• Safety Statements: 16-26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2COC(=O)C2=C(C(=C1OC)CC=C(C)CCC(=O)O)OC3C(C(C(C(O3)C(=O)O)O)O)O
• Isomeric SMILES: CC1=C2COC(=O)C2=C(C(=C1OC)C/C=C(\C)/CCC(=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)C(=O)O)O)O)O
• Uses: A 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 monoph osphate dehydrogenase, an enzyme involved in the de novo synthesis of purine nucleotides. A metabolite of Mycophenolic Acid (M831500), 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 the de novo synthesis of purine nucleotides.

Technology Process of Mycophenolic acid glucuronide

There total 5 articles about Mycophenolic acid glucuronide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

methyl mycophenolate 7-O-(2,3,4-tri-O-acetyl-methyl ester)-β-D-glucopyranuronoside (1186295-40-8) → Mycophenolic acid 7-O-glucuronide (31528-44-6)

Guidance literature:

With methanol; sodium hydroxide; In water; at 0 - 20 ℃;

DOI:10.1016/j.tetlet.2009.06.060

Reference yield:

mycophenolic acid (24280-93-1) + UDP-glucuronic acid (2616-64-0) → Mycophenolic acid 7-O-glucuronide (31528-44-6)

Guidance literature:

With tris hydrochloride; magnesium chloride; In water; at 37 ℃; for 0.5h; pH=7.45; Kinetics; Enzymatic reaction;

DOI:10.1016/j.dmpk.2015.10.004

Reference yield:

sodium mycophenolate + UDP-glucuronic acid → Mycophenolic acid 7-O-glucuronide (31528-44-6) + Mycophenolic acid acyl glucuronide (99043-04-6)

Guidance literature:

With sodium hydroxide; horse liver homogenate; magnesium chloride; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid; UDPGA-transferase; In water; dimethyl sulfoxide; at 37 ℃; for 20h; pH=7; Further Variations:; Temperatures; pH-values; Reagents; ratio of catalyst; Product distribution; Enzymatic reaction;

DOI:10.1002/adsc.200303044

upstream raw materials:

methyl mycophenolate 7-O-(2,3,4-tri-O-acetyl-methyl ester)-β-D-glucopyranuronoside

mycophenolic acid

UDP-glucuronic acid

UDP-glucuronic acid

Refernces

• 1、 Yoshimura, Kazuaki,Yano, Ikuko,Kawanishi, Misaki,Nakagawa, Shunsaku,Yonezawa, Atsushi,Matsubara, Kazuo. "Pharmacokinetics and pharmacodynamics of mycophenolic acid in Nagase analbuminemic rats: Evaluation of protein binding effects using the modeling and simulation approach". . p. 441 - 448. Retrieved 2015.
• 2、 Wu, Baojian,Wang, Xiaoqiang,Zhang, Shuxing,Hu, Ming. "Accurate prediction of glucuronidation of structurally diverse phenolics by human UGT1A9 using combined experimental and in silico approaches". experimental part. p. 1544 - 1561. Retrieved 2012/07/27.