Adenophostin a

Base Information

• Chemical Name: Adenophostin a
• CAS No.: 149091-92-9
• Molecular Formula: C₁₆H₂₆N₅O₁₈P₃
• Molecular Weight: 669.326
• UNII: 2S7AR5SVD7
• DSSTox Substance ID: DTXSID10164167
• Nikkaji Number: J569.664J
• Wikipedia: Adenophostin
• Wikidata: Q4682254
• Metabolomics Workbench ID: 68147
• ChEMBL ID: CHEMBL204385
• Mol file: 149091-92-9.mol

Synonyms:adenophostin A

Chemical Property of Adenophostin a

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1155.6°Cat760mmHg
• PKA: 1.83±0.10(Predicted)
• Flash Point: 652.7°C
• PSA: 387.71000
• Density: 2.52g/cm³
• LogP: -3.22360
• XLogP3: -7
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 22
• Rotatable Bond Count: 11
• Exact Mass: 669.04856999
• Heavy Atom Count: 42
• Complexity: 1080

Purity/Quality:

99% ^*data from raw suppliers

ADENOPHOSTIN A 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)OC4C(C(C(C(O4)CO)OP(=O)(O)O)OP(=O)(O)O)O)OP(=O)(O)O)N
• Isomeric SMILES: C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)OP(=O)(O)O)OP(=O)(O)O)O)OP(=O)(O)O)N

Technology Process of Adenophostin a

There total 4 articles about Adenophostin a 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: 92.0%

2'',5',6''-tri-O-benzyl-2',3'',4''-tris(dibenzyloxyphosphoryl)-3'-O-α-D-glucopyranosyl adenosine → adenophostin A (149091-92-9)

Guidance literature:

With cyclohexene; palladium dihydroxide; In methanol; water; for 2.5h; Heating;

DOI:10.1016/S0957-4166(99)00491-7

Reference yield: 65.0%

Phosphoric acid mono-{(2R,3R,4R,5R,6R)-6-[(2R,3R,4R,5R)-5-(6-amino-purin-9-yl)-2-hydroxymethyl-4-phosphonooxy-tetrahydro-furan-3-yloxy]-5-benzyloxy-2-hydroxymethyl-4-phosphonooxy-tetrahydro-pyran-3-yl} ester → adenophostin A (149091-92-9)

Guidance literature:

With hydrogen; palladium; In water;

DOI:10.1016/0040-4039(96)00632-6

Reference yield:

C47H50N5O18P3 → adenophostin A (149091-92-9)

Guidance literature:

With hydrogen; palladium; In ethanol; water; for 24h; Yield given;

DOI:10.1016/00404-0399(50)0916Z-

upstream raw materials:

Adenophostin B

Refernces

Contribution of phosphates and adenine to the potency of adenophostins at the IP₃ receptor: Synthesis of all possible bisphosphates of adenophostin A

10.1021/jm201571p

The study investigated the role of different phosphate groups and adenosine motifs in adenophostin A (AdA), a potent agonist of the D-inositol 1,4,5-triphosphate receptor (IP3R). The researchers synthesized all three possible diphosphate analogs of AdA and glucose 3,4-bisphosphate (7). They found that 2-dephospho-AdA (6), which mimics Ins(4,5)P2, was only 4-fold less potent than IP3, while 7 was 400-fold less potent. Even 3″-dephospho-AdA (5), which lacks one vicinal diphosphate group, has measurable activity. This study concludes that the adenosine motif has a direct role in promoting adenylate cyclase potency that is independent of the 2′-phosphate group and that the vicinal diphosphate motif is not essential for IP3R activity. The results suggest that it may be possible to design potent agonists using only two of the three phosphates, and a model for possible interaction with adenine-R504 supports the activity of 5 and 6.

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