Herbicidin A

Base Information

• Chemical Name: Herbicidin A
• CAS No.: 55353-31-6
• Molecular Formula: C23H29N5O11
• Molecular Weight: 551.5033
• DSSTox Substance ID: DTXSID801317929
• Wikidata: Q76386837
• Metabolomics Workbench ID: 130455
• ChEMBL ID: CHEMBL3109448
• Mol file: 55353-31-6.mol

Synonyms:Herbicidin A;Herbicidin-A;55353-31-6;alpha-L-ido-D-lyxo-5-Undeculo-5,9-pyranosonic acid, 11-C-(6-amino-9H-purin-9-yl)-2,6:8,11-dianhydro-7-deoxy-10-O-methyl-, methyl ester, 4-(2-(hydroxymethyl)-2-butenoate), (4(E),11R)-;(11R)-11-C-(6-Amino-9H-purin-9-yl)-2,6;methyl (1R,3S,4R,5R,7R,9R,11S,12S,13S)-5-(6-aminopurin-9-yl)-1,12-dihydroxy-13-[(E)-2-(hydroxymethyl)but-2-enoyl]oxy-4-methoxy-2,6,10-trioxatricyclo[7.4.0.03,7]tridecane-11-carboxylate;C23H29N5O11;C23-H29-N5-O11;CHEMBL3109448;DTXSID801317929;AKOS040755042;HY-124438;LS-158510;CS-0086467;methyl (2R,3R,3aS,4aR,5S,6S,7S,8aR,9aR)-2-(6-aminopurin-9-yl)-4a,6-dihydroxy-5-[(E)-2-(hydroxymethyl)but-2-enoyl]oxy-3-methoxy-3,3a,5,6,7,8a,9,9a-octahydro-2H-furo[[?]]pyrano[[?]]pyran-7-carboxylate

Chemical Property of Herbicidin A

Chemical Property:

• Vapor Pressure: 6.25E-29mmHg at 25°C
• Boiling Point: 826.5°Cat760mmHg
• PKA: 10.17±0.70(Predicted)
• Flash Point: 453.6°C
• PSA: 219.83000
• Density: 1.78g/cm³
• LogP: -1.46870
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 8
• Exact Mass: 551.18635676
• Heavy Atom Count: 39
• Complexity: 973

Purity/Quality:

99% ^*data from raw suppliers

HerbicidinA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C(CO)C(=O)OC1C(C(OC2C1(OC3C(C2)OC(C3OC)N4C=NC5=C(N=CN=C54)N)O)C(=O)OC)O
• Isomeric SMILES: C/C=C(\CO)/C(=O)O[C@H]1[C@@H]([C@H](O[C@H]2[C@]1(O[C@H]3[C@@H](C2)O[C@H]([C@@H]3OC)N4C=NC5=C(N=CN=C54)N)O)C(=O)OC)O
• Description: Herbicidin A is an adenine nucleoside antibiotic originally isolated from S. saganonensis that exhibits herbicidal activity, particularly against dicotyledonous plants. It prevents rice seed germination (MIC = 6.25 μg/ml) and completely protects young rice plants from X. oryzae-induced leaf blight when applied at 100 ppm. In HEK293 cells, herbicidin A inhibits TNF-α-induced NF-κB activity and induces cytotoxicity (IC50s = 1.8 and 2.7 μM, respectively).
• Uses: Herbicidin A is the major analogue of a family of adenosine nucleosides containing a complex tricyclic saccharide originally isolated from Streptomyces saganonensis, reported by researchers at Sankyo in 1976. Hebicidin A is a potent herbicide with selective activity against dicotyledonous plants. The mode of action and broader pharmacology of herbicidin A has received little attention due to its restricted availability. Herbicidin A is a chemical with antibacterial and herbicidal activity.

Technology Process of Herbicidin A

There total 1 articles about Herbicidin 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:

methanol (67-56-1) + herbicidin H → herbicidin A (55353-31-6)

Guidance literature:

With B₁₂-dependent radical S-adenosyl-L-methionine enzyme; herbicidins cluster contain methyltransferases HbcG; In aq. phosphate buffer; at 30 ℃; for 8h; pH=7; Enzymatic reaction;

DOI:10.1021/acs.orglett.9b00066

Reference yield:

herbicidin A (55353-31-6) → herbicidin B (55353-32-7)

Guidance literature:

Multi-step reaction with 2 steps

1: coenzyme A; herbicidins cluster contain serine hydrolase HbcH / aq. phosphate buffer / 8 h / 30 °C / pH 7 / Enzymatic reaction

2: B₁₂-dependent radical S-adenosyl-L-methionine enzyme; herbicidins cluster contain methyltransferases HbcG / aq. phosphate buffer / 8 h / 30 °C / pH 7 / Enzymatic reaction

With coenzyme A; B₁₂-dependent radical S-adenosyl-L-methionine enzyme; herbicidins cluster contain methyltransferases HbcG; herbicidins cluster contain serine hydrolase HbcH; In aq. phosphate buffer;

DOI:10.1021/acs.orglett.9b00066

upstream raw materials:

methanol

Downstream raw materials:

herbicidin B

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