Orotidine-5'-monophosphate

Base Information

• Chemical Name: Orotidine-5'-monophosphate
• CAS No.: 2149-82-8
• Molecular Formula: C10H13 N2 O11 P
• Molecular Weight: 368.194
• UNII: H0ARN8U4Y9
• DSSTox Substance ID: DTXSID40944090
• Nikkaji Number: J13.801K
• Wikipedia: Orotidine_5%27-monophosphate,Orotidine_5'-monophosphate
• Wikidata: Q27098253
• Metabolomics Workbench ID: 37143
• ChEMBL ID: CHEMBL1207358
• Mol file: 2149-82-8.mol

Synonyms:5-(dihydrogen phosphate)orotidine;orotidine 5'-monophosphate;orotidylic acid

Chemical Property of Orotidine-5'-monophosphate

Chemical Property:

• Boiling Point: °Cat760mmHg
• PKA: 1.86±0.10(Predicted)
• Flash Point: °C
• PSA: 227.17000
• Density: 2g/cm³
• LogP: -3.08270
• XLogP3: -4.2
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 5
• Exact Mass: 368.02569623
• Heavy Atom Count: 24
• Complexity: 643

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(N(C(=O)NC1=O)C2C(C(C(O2)COP(=O)(O)O)O)O)C(=O)O
• Isomeric SMILES: C1=C(N(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O)C(=O)O

Technology Process of Orotidine-5'-monophosphate

There total 7 articles about Orotidine-5'-monophosphate 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: 28.0%

D-Ribose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) + orotic acid (65-86-1,58915-47-2,6784-70-9) → orotidine 5'-monophosphate (2149-82-8)

Guidance literature:

With glycylglycine; phosphoenolpyruvic acid; potassium chloride; adenosine 5'-triphosphate disodium salt; magnesium chloride; diothiothreitol; adenylate kinase; pyruvate kinase; ribokinase; phospho-D-ribosyl-1-pyrophosphate synthase; PfOPRT; In water; at 37 ℃; for 20h; Enzymatic reaction;

Reference yield:

((2R,3S,4R,5R)-5-(6-cyano-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate (68244-52-0) → orotidine 5'-monophosphate (2149-82-8)

Guidance literature:

With water; sodium hydroxide; at 20 ℃; for 96h;

DOI:10.1039/b812979g

Reference yield:

C10H13N2O11P*H3N*CH2O3 → orotidine 5'-monophosphate (2149-82-8)

Guidance literature:

With hydrogenchloride; In water; pH=5; Inert atmosphere;

DOI:10.1021/bi401117y

upstream raw materials:

((2R,3S,4R,5R)-5-(6-cyano-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

D-Ribose

orotic acid

5-phosphoribosyl-1-pyrophosphate

Downstream raw materials:

orotic acid

5-phosphoribosyl-1-pyrophosphate

5'-Uridylic Acid

Refernces

• 1、 Goryanova, Bogdana,Goldman, Lawrence M.,Amyes, Tina L.,Gerlt, John A.,Richard, John P.. "Role of a guanidinium cation-phosphodianion pair in stabilizing the vinyl carbanion intermediate of orotidine 5′-phosphate decarboxylase-catalyzed reactions". . p. 7500 - 7511. Retrieved 2013.
• 2、 -. "Transition state structure of orotate phosphoribosyl transferases and uses thereof". Page/Page column 4. . Retrieved 2011/12/14.