53185-12-9,MFCD18782654
Catalog No.:AA00DB3D

53185-12-9 | Fagomine

Pack Size
Purity
Availability
Price(USD)
Quantity
  
5mg
98%
1 week  
$765.00   $535.00
- +
10mg
98%
1 week  
$1,193.00   $835.00
- +
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA00DB3D
Chemical Name:
Fagomine
CAS Number:
53185-12-9
Molecular Formula:
C6H13NO3
Molecular Weight:
147.1723
MDL Number:
MFCD18782654
SMILES:
OC[C@H]1NCC[C@H]([C@@H]1O)O
Properties
Computed Properties
 
Complexity:
109  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
3  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
10  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0  
Rotatable Bond Count:
1  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
-1.4  

Downstream Synthesis Route
4426-83-9    53185-12-9   
N-(N'-octythiocarbamoyl)-D-fagomine 

[1]Mena-Barragán,Teresa;García-Moreno,M.Isabel;Nanba,Eiji;Higaki,Katsumi;Concia,AldaLisa;Clapés,Pere;GarcíaFernández,JoséManuel;OrtizMellet,Carmen[EuropeanJournalofMedicinalChemistry,2016,vol.121,p.880-891]

4426-83-9    53185-12-9   
5N,6S-(N'-octyliminomethylidene)-6-thio-D-fagomine 

[1]Mena-Barragán,Teresa;García-Moreno,M.Isabel;Nanba,Eiji;Higaki,Katsumi;Concia,AldaLisa;Clapés,Pere;GarcíaFernández,JoséManuel;OrtizMellet,Carmen[EuropeanJournalofMedicinalChemistry,2016,vol.121,p.880-891]

Literature

Title: D-Fagomine lowers postprandial blood glucose and modulates bacterial adhesion.

Journal: The British journal of nutrition 20120601

Title: [Study on chemical constituents of Peganum multisectum].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20111101

Title: Docking and SAR studies of D- and L-isofagomine isomers as human β-glucocerebrosidase inhibitors.

Journal: Bioorganic & medicinal chemistry 20110601

Title: Determination of iminosugars in mulberry leaves and silkworms using hydrophilic interaction chromatography-tandem mass spectrometry.

Journal: Analytical biochemistry 20100915

Title: Synthesis and inhibitory activities of novel C-3 substituted azafagomines: a new type of selective inhibitors of α-L-fucosidases.

Journal: Bioorganic & medicinal chemistry 20100701

Title: Cytotoxicity and enzymatic activity inhibition in cell lines treated with novel iminosugar derivatives.

Journal: Glycoconjugate journal 20100201

Title: In vitro inhibition of glycogen-degrading enzymes and glycosidases by six-membered sugar mimics and their evaluation in cell cultures.

Journal: Bioorganic & medicinal chemistry 20080801

Title: Microarray expression profiling of Arabidopsis thaliana L. in response to allelochemicals identified in buckwheat.

Journal: Journal of experimental botany 20080801

Title: [Alkaloid constituents from silkworm dropping of Bombyx mori].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20071101

Title: [Chemical constituents from leaves of Morus multicaulis].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20070401

Title: Fructose-6-phosphate aldolase in organic synthesis: preparation of D-fagomine, N-alkylated derivatives, and preliminary biological assays.

Journal: Organic letters 20061221

Title: General synthesis and biological evaluation of alpha-1-C-substituted derivatives of fagomine (2-deoxynojirimycin-alpha-C-glycosides).

Journal: Bioorganic & medicinal chemistry 20050315

Title: Iminosugars: potential inhibitors of liver glycogen phosphorylase.

Journal: Bioorganic & medicinal chemistry 20010301

Title: Inhibition of HIV replication by amino-sugar derivatives.

Journal: FEBS letters 19880912

Title: Mena-Barragán T, et al. Inhibitor versus chaperone behaviour of d-fagomine, DAB and LAB sp2-iminosugar conjugates againstglycosidases: A structure-activity relationship study in Gaucher fibroblasts. Eur J Med Chem. 2015 Aug 31. pii: S0223-5234(15)30222-1.

Title: Ramos-Romero S, et al. Effect of (D)-fagomine on excreted Enterobacteria and weight gain in rats fed a high-fat high-sucrose diet. Obesity (Silver Spring). 2014 Apr;22(4):976-9.

Title: Molinar-Toribio E, et al. D-Fagomine attenuates metabolic alterations induced by a high-energy-dense diet in rats. Food Funct. 2015 Aug;6(8):2614-9.

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SDS
Tags:53185-12-9 Molecular Formula|53185-12-9 MDL|53185-12-9 SMILES|53185-12-9 Fagomine
Catalog No.: AA00DB3D
53185-12-9,MFCD18782654
53185-12-9 | Fagomine
Pack Size: 5mg
Purity: 98%
1 week
$765.00 $535.00
Pack Size: 10mg
Purity: 98%
1 week
$1,193.00 $835.00
Quantity
- +
Add to Card
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bulk Quotation Request
Technical Information
Catalog Number: AA00DB3D
Chemical Name: Fagomine
CAS Number: 53185-12-9
Molecular Formula: C6H13NO3
Molecular Weight: 147.1723
MDL Number: MFCD18782654
SMILES: OC[C@H]1NCC[C@H]([C@@H]1O)O
Properties
Complexity: 109  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 3  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 10  
Hydrogen Bond Acceptor Count: 4  
Hydrogen Bond Donor Count: 4  
Isotope Atom Count: 0  
Rotatable Bond Count: 1  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: -1.4  
Downstream Synthesis Route
4426-83-9    53185-12-9   
N-(N'-octythiocarbamoyl)-D-fagomine 

[1]Mena-Barragán,Teresa;García-Moreno,M.Isabel;Nanba,Eiji;Higaki,Katsumi;Concia,AldaLisa;Clapés,Pere;GarcíaFernández,JoséManuel;OrtizMellet,Carmen[EuropeanJournalofMedicinalChemistry,2016,vol.121,p.880-891]

4426-83-9    53185-12-9   
5N,6S-(N'-octyliminomethylidene)-6-thio-D-fagomine 

[1]Mena-Barragán,Teresa;García-Moreno,M.Isabel;Nanba,Eiji;Higaki,Katsumi;Concia,AldaLisa;Clapés,Pere;GarcíaFernández,JoséManuel;OrtizMellet,Carmen[EuropeanJournalofMedicinalChemistry,2016,vol.121,p.880-891]

Literature fold

Title: D-Fagomine lowers postprandial blood glucose and modulates bacterial adhesion.

Journal: The British journal of nutrition20120601

Title: [Study on chemical constituents of Peganum multisectum].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials20111101

Title: Docking and SAR studies of D- and L-isofagomine isomers as human β-glucocerebrosidase inhibitors.

Journal: Bioorganic & medicinal chemistry20110601

Title: Determination of iminosugars in mulberry leaves and silkworms using hydrophilic interaction chromatography-tandem mass spectrometry.

Journal: Analytical biochemistry20100915

Title: Synthesis and inhibitory activities of novel C-3 substituted azafagomines: a new type of selective inhibitors of α-L-fucosidases.

Journal: Bioorganic & medicinal chemistry20100701

Title: Cytotoxicity and enzymatic activity inhibition in cell lines treated with novel iminosugar derivatives.

Journal: Glycoconjugate journal20100201

Title: In vitro inhibition of glycogen-degrading enzymes and glycosidases by six-membered sugar mimics and their evaluation in cell cultures.

Journal: Bioorganic & medicinal chemistry20080801

Title: Microarray expression profiling of Arabidopsis thaliana L. in response to allelochemicals identified in buckwheat.

Journal: Journal of experimental botany20080801

Title: [Alkaloid constituents from silkworm dropping of Bombyx mori].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials20071101

Title: [Chemical constituents from leaves of Morus multicaulis].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica20070401

Title: Fructose-6-phosphate aldolase in organic synthesis: preparation of D-fagomine, N-alkylated derivatives, and preliminary biological assays.

Journal: Organic letters20061221

Title: General synthesis and biological evaluation of alpha-1-C-substituted derivatives of fagomine (2-deoxynojirimycin-alpha-C-glycosides).

Journal: Bioorganic & medicinal chemistry20050315

Title: Iminosugars: potential inhibitors of liver glycogen phosphorylase.

Journal: Bioorganic & medicinal chemistry20010301

Title: Inhibition of HIV replication by amino-sugar derivatives.

Journal: FEBS letters19880912

Title: Mena-Barragán T, et al. Inhibitor versus chaperone behaviour of d-fagomine, DAB and LAB sp2-iminosugar conjugates againstglycosidases: A structure-activity relationship study in Gaucher fibroblasts. Eur J Med Chem. 2015 Aug 31. pii: S0223-5234(15)30222-1.

Title: Ramos-Romero S, et al. Effect of (D)-fagomine on excreted Enterobacteria and weight gain in rats fed a high-fat high-sucrose diet. Obesity (Silver Spring). 2014 Apr;22(4):976-9.

Title: Molinar-Toribio E, et al. D-Fagomine attenuates metabolic alterations induced by a high-energy-dense diet in rats. Food Funct. 2015 Aug;6(8):2614-9.

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