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KRN7000

CAS No.:
158021-47-7
Catalog Number:
AG00AE7J
Molecular Formula:
C50H99NO9
Molecular Weight:
858.3224
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥96%
1 week
United States
$347
- +
Product Description
Catalog Number:
AG00AE7J
Chemical Name:
KRN7000
CAS Number:
158021-47-7
Molecular Formula:
C50H99NO9
Molecular Weight:
858.3224
MDL Number:
MFCD00939559
IUPAC Name:
N-[(2S,3S,4R)-3,4-dihydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadecan-2-yl]hexacosanamide
InChI:
InChI=1S/C50H99NO9/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-27-29-31-33-35-37-39-45(54)51-42(41-59-50-49(58)48(57)47(56)44(40-52)60-50)46(55)43(53)38-36-34-32-30-28-16-14-12-10-8-6-4-2/h42-44,46-50,52-53,55-58H,3-41H2,1-2H3,(H,51,54)/t42-,43+,44+,46-,47-,48-,49+,50-/m0/s1
InChI Key:
VQFKFAKEUMHBLV-BYSUZVQFSA-N
SMILES:
CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@@H]([C@@H](CCCCCCCCCCCCCC)O)O)CO[C@H]1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)O)O
UNII:
WX671898JF
Properties
Complexity:
928  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
8  
Defined Bond Stereocenter Count:
0
Exact Mass:
857.732g/mol
Formal Charge:
0
Heavy Atom Count:
60  
Hydrogen Bond Acceptor Count:
9  
Hydrogen Bond Donor Count:
7  
Isotope Atom Count:
0
Molecular Weight:
858.34g/mol
Monoisotopic Mass:
857.732g/mol
Rotatable Bond Count:
44  
Topological Polar Surface Area:
169A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
16  
Literature
Title Journal
Chronic alcohol consumption enhances iNKT cell maturation and activation. Toxicology and applied pharmacology 20150115
Enhanced TCR footprint by a novel glycolipid increases NKT-dependent tumor protection. Journal of immunology (Baltimore, Md. : 1950) 20130915
Bacterial CD1d-restricted glycolipids induce IL-10 production by human regulatory T cells upon cross-talk with invariant NKT cells. Journal of immunology (Baltimore, Md. : 1950) 20130901
Slam haplotype 2 promotes NKT but suppresses Vγ4+ T-cell activation in coxsackievirus B3 infection leading to increased liver damage but reduced myocarditis. The American journal of pathology 20130201
Recognition of microbial and mammalian phospholipid antigens by NKT cells with diverse TCRs. Proceedings of the National Academy of Sciences of the United States of America 20130129
Lack of PD-L1 expression by iNKT cells improves the course of influenza A infection. PloS one 20130101
CD1d-dependent, iNKT-cell cytotoxicity against keratinocytes in allergic contact dermatitis. Experimental dermatology 20121201
Human and mouse type I natural killer T cell antigen receptors exhibit different fine specificities for CD1d-antigen complex. The Journal of biological chemistry 20121109
The molecular basis for recognition of CD1d/α-galactosylceramide by a human non-Vα24 T cell receptor. PLoS biology 20121001
Key role for respiratory CD103(+) dendritic cells, IFN-γ, and IL-17 in protection against Streptococcus pneumoniae infection in response to α-galactosylceramide. The Journal of infectious diseases 20120901
Type II natural killer T cells use features of both innate-like and conventional T cells to recognize sulfatide self antigens. Nature immunology 20120901
C-Glycosphingolipids with an exo-methylene substituent: stereocontrolled synthesis and immunostimulation of mouse and human natural killer T lymphocytes. Chembiochem : a European journal of chemical biology 20120813
RCAI-84, 91, and 105-108, ureido and thioureido analogs of KRN7000: their synthesis and bioactivity for mouse lymphocytes to produce Th1-biased cytokines. Bioorganic & medicinal chemistry 20120715
Activation of invariant natural killer T cells by lipid excess promotes tissue inflammation, insulin resistance, and hepatic steatosis in obese mice. Proceedings of the National Academy of Sciences of the United States of America 20120508
Bacterial species-characteristic profiles of molecular species, and the antigenicity of phospholipids and glycolipids in symbiotic Lactobacillus, Staphylococcus and Streptococcus species. Glycoconjugate journal 20120501
Lysophospholipid presentation by CD1d and recognition by a human Natural Killer T-cell receptor. The EMBO journal 20120418
Structural and functional characterization of a novel nonglycosidic type I NKT agonist with immunomodulatory properties. Journal of immunology (Baltimore, Md. : 1950) 20120301
3-fluoro- and 3,3-difluoro-3,4-dideoxy-KRN7000 analogues as new potent immunostimulator agents: total synthesis and biological evaluation in human invariant natural killer T cells and mice. Journal of medicinal chemistry 20120209
Structural basis for the recognition of C20:2-αGalCer by the invariant natural killer T cell receptor-like antibody L363. The Journal of biological chemistry 20120106
Natural variations at position 93 of the invariant Vα24-Jα18 α chain of human iNKT-cell TCRs strongly impact on CD1d binding. European journal of immunology 20120101
Crystal structures of bovine CD1d reveal altered αGalCer presentation and a restricted A' pocket unable to bind long-chain glycolipids. PloS one 20120101
Activation of Invariant NKT cells with glycolipid ligand α-galactosylceramide ameliorates glucose-6-phosphate isomerase peptide-induced arthritis. PloS one 20120101
Divergent synthetic approach to 6''-modified α-GalCer analogues. Organic & biomolecular chemistry 20111221
Total synthesis of α-1C-galactosylceramide, an immunostimulatory C-glycosphingolipid, and confirmation of the stereochemistry in the first-generation synthesis. The Journal of organic chemistry 20111104
Invariant NKT cell defects in vitamin D receptor knockout mice prevents experimental lung inflammation. Journal of immunology (Baltimore, Md. : 1950) 20111101
Prevention of type 1 diabetes by inducing subclinical dermatitis on a small area. Diabetes/metabolism research and reviews 20111101
Unique interplay between sugar and lipid in determining the antigenic potency of bacterial antigens for NKT cells. PLoS biology 20111101
Invariant natural killer T cells recognize glycolipids from pathogenic Gram-positive bacteria. Nature immunology 20111001
Cutting edge: structural basis for the recognition of β-linked glycolipid antigens by invariant NKT cells. Journal of immunology (Baltimore, Md. : 1950) 20110901
Recognition of β-linked self glycolipids mediated by natural killer T cell antigen receptors. Nature immunology 20110731
A semi-invariant Vα10+ T cell antigen receptor defines a population of natural killer T cells with distinct glycolipid antigen-recognition properties. Nature immunology 20110612
Innate and cytokine-driven signals, rather than microbial antigens, dominate in natural killer T cell activation during microbial infection. The Journal of experimental medicine 20110606
Galactose-modified iNKT cell agonists stabilized by an induced fit of CD1d prevent tumour metastasis. The EMBO journal 20110601
Functional invariant NKT cells in pig lungs regulate the airway hyperreactivity: a potential animal model. Journal of clinical immunology 20110401
A molecular basis for the exquisite CD1d-restricted antigen specificity and functional responses of natural killer T cells. Immunity 20110325
A molecular basis for NKT cell recognition of CD1d-self-antigen. Immunity 20110325
Synthesis of a versatile building block for the preparation of 6-N-derivatized α-galactosyl ceramides: rapid access to biologically active glycolipids. The Journal of organic chemistry 20110107
Synthesis of truncated analogues of the iNKT cell agonist, α-galactosyl ceramide (KRN7000), and their biological evaluation. Bioorganic & medicinal chemistry 20110101
Development of spontaneous anergy in invariant natural killer T cells in a mouse model of dyslipidemia. Arteriosclerosis, thrombosis, and vascular biology 20100901
Synthesis and biological activity of ester and ether analogues of alpha-galactosylceramide (KRN7000). Carbohydrate research 20100816
Invariant NKT cells are required for antitumor responses induced by host-versus-graft responses. Journal of immunology (Baltimore, Md. : 1950) 20100815
Dietary fatty acids modulate antigen presentation to hepatic NKT cells in nonalcoholic fatty liver disease. Journal of lipid research 20100701
Plasticity of invariant NKT cell regulation of allergic airway disease is dependent on IFN-gamma production. Journal of immunology (Baltimore, Md. : 1950) 20100701
Slam haplotypes modulate the response to lipopolysaccharide in vivo through control of NKT cell number and function. Journal of immunology (Baltimore, Md. : 1950) 20100701
Synthesis and biological activity of alpha-L-fucosyl ceramides, analogues of the potent agonist, alpha-D-galactosyl ceramide KRN7000. Bioorganic & medicinal chemistry letters 20100601
Fatty acid amide hydrolase shapes NKT cell responses by influencing the serum transport of lipid antigen in mice. The Journal of clinical investigation 20100601
Innate-like control of human iNKT cell autoreactivity via the hypervariable CDR3beta loop. PLoS biology 20100601
CD1d-dependent B-cell help by NK-like T cells leads to enhanced and sustained production of Bacillus anthracis lethal toxin-neutralizing antibodies. Infection and immunity 20100401
A CD1d-dependent antagonist inhibits the activation of invariant NKT cells and prevents development of allergen-induced airway hyperreactivity. Journal of immunology (Baltimore, Md. : 1950) 20100215
Syntheses and biological activities of KRN7000 analogues having aromatic residues in the acyl and backbone chains with varying stereochemistry. Bioorganic & medicinal chemistry letters 20100201
Lipid binding orientation within CD1d affects recognition of Borrelia burgorferi antigens by NKT cells. Proceedings of the National Academy of Sciences of the United States of America 20100126
PD-L1 and PD-L2 modulate airway inflammation and iNKT-cell-dependent airway hyperreactivity in opposing directions. Mucosal immunology 20100101
Mechanisms for glycolipid antigen-driven cytokine polarization by Valpha14i NKT cells. Journal of immunology (Baltimore, Md. : 1950) 20100101
Bacillus anthracis lethal toxin disrupts TCR signaling in CD1d-restricted NKT cells leading to functional anergy. PLoS pathogens 20090901
Focus on the controversial activation of human iNKT cells by 4-deoxy analogue of KRN7000. Journal of medicinal chemistry 20090813
Synthesis and biological activity of alpha-galactosyl ceramide KRN7000 and galactosyl (alpha1-->2) galactosyl ceramide. Bioorganic & medicinal chemistry letters 20090801
Skin and peripheral lymph node invariant NKT cells are mainly retinoic acid receptor-related orphan receptor (gamma)t+ and respond preferentially under inflammatory conditions. Journal of immunology (Baltimore, Md. : 1950) 20090801
Differential recognition of CD1d-alpha-galactosyl ceramide by the V beta 8.2 and V beta 7 semi-invariant NKT T cell receptors. Immunity 20090717
Cutting edge: B and T lymphocyte attenuator signaling on NKT cells inhibits cytokine release and tissue injury in early immune responses. Journal of immunology (Baltimore, Md. : 1950) 20090701
Induction of airway hyperreactivity by IL-25 is dependent on a subset of invariant NKT cells expressing IL-17RB. Journal of immunology (Baltimore, Md. : 1950) 20090415
Alpha-S-GalCer: synthesis and evaluation for iNKT cell stimulation. Bioorganic & medicinal chemistry letters 20081215
Synthesis of alpha-galactosyl ceramide (KRN7000) and analogues thereof via a common precursor and their preliminary biological assessment. The Journal of organic chemistry 20081121
Synthesis and in vivo evaluation of 4-deoxy-4,4-difluoro-KRN7000. Organic letters 20081016
The first synthesis of a thioglycoside analogue of the immunostimulant KRN7000. Organic letters 20081016
RCAI-17, 22, 24-26, 29, 31, 34-36, 38-40, and 88, the analogs of KRN7000 with a sulfonamide linkage: their synthesis and bioactivity for mouse natural killer T cells to produce Th2-biased cytokines. Bioorganic & medicinal chemistry 20081001
Prolongation of cardiac allograft survival by rapamycin and the invariant natural killer T cell glycolipid agonist OCH. Transplantation 20080815
Alpha-lactosylceramide as a novel 'sugar-capped' CD1d ligand for natural killer T cells: biased cytokine profile and therapeutic activities. Chembiochem : a European journal of chemical biology 20080616
Glycolipid-activated NKT cells support the induction of persistent plasma cell responses and antibody titers. European journal of immunology 20080401
RCAI-8, 9, 18, 19, and 49-52, conformationally restricted analogues of KRN7000 with an azetidine or a pyrrolidine ring: Their synthesis and bioactivity for mouse natural killer T cells to produce cytokines. Bioorganic & medicinal chemistry 20080115
Immunization with dendritic cells loaded with alpha-galactosylceramide at priming phase, but not at boosting phase, enhances cytotoxic T lymphocyte activity against infection by intracellular bacteria. FEMS immunology and medical microbiology 20071101
iNKT cells require CCR4 to localize to the airways and to induce airway hyperreactivity. Journal of immunology (Baltimore, Md. : 1950) 20071001
A general and stereoselective route to alpha- or beta-galactosphingolipids via a common four-carbon building block. The Journal of organic chemistry 20070928
A Y chromosome-linked factor impairs NK T development. Journal of immunology (Baltimore, Md. : 1950) 20070915
CD1d-lipid-antigen recognition by the semi-invariant NKT T-cell receptor. Nature 20070705
Minimum structure requirement of immunomodulatory glycolipids for predominant Th2 cytokine induction and the discovery of non-linear phytosphingosine analogs. Bioorganic & medicinal chemistry letters 20070515
Synthesis and evaluation of 1,2,3-triazole containing analogues of the immunostimulant alpha-GalCer. Journal of medicinal chemistry 20070208
During acute Trypanosoma cruzi infection highly susceptible mice deficient in natural killer cells are protected by a single alpha-galactosylceramide treatment. Immunology 20061101
The CD1d-binding glycolipid alpha-galactosylceramide enhances humoral immunity to T-dependent and T-independent antigen in a CD1d-dependent manner. Immunology 20060901
Synthesis and biological evaluation of alpha-galactosylceramide (KRN7000) and isoglobotrihexosylceramide (iGb3). Bioorganic & medicinal chemistry letters 20060415
Design of natural killer T cell activators: structure and function of a microbial glycosphingolipid bound to mouse CD1d. Proceedings of the National Academy of Sciences of the United States of America 20060314
Chemoenzymatic syntheses of iGb3 and Gb3. Organic letters 20060302
Synthesis and evaluation of sphinganine analogues of KRN7000 and OCH. The Journal of organic chemistry 20051209
NK T cell activation promotes Chlamydia trachomatis infection in vivo. Journal of immunology (Baltimore, Md. : 1950) 20050901
The crystal structure of human CD1d with and without alpha-galactosylceramide. Nature immunology 20050801
Structure and function of a potent agonist for the semi-invariant natural killer T cell receptor. Nature immunology 20050801
Sustained expansion of NKT cells and antigen-specific T cells after injection of alpha-galactosyl-ceramide loaded mature dendritic cells in cancer patients. The Journal of experimental medicine 20050502
Quantitative and qualitative differences in the in vivo response of NKT cells to distinct alpha- and beta-anomeric glycolipids. Journal of immunology (Baltimore, Md. : 1950) 20040915
Enhancement of the synthetic ligand-mediated function of liver NK1.1Ag+ T cells in mice by interleukin-12 pretreatment. Immunology 20040901
Human NKT cells express granulysin and exhibit antimycobacterial activity. Journal of immunology (Baltimore, Md. : 1950) 20030315
Total enantioselective synthesis and in vivo biological evaluation of a novel fluorescent BODIPY alpha-galactosylceramide. Chembiochem : a European journal of chemical biology 20030103
No inhibition of urinary bladder carcinogenesis in rats with intravesical instillation of alpha-galactosylceramide. Asian Pacific journal of cancer prevention : APJCP 20030101
Disruption of T helper 2-immune responses in Epstein-Barr virus-induced gene 3-deficient mice. Proceedings of the National Academy of Sciences of the United States of America 20021224
Enhancing effects of (2S,3S,4R)-1-O-(alpha-D-galactopyranosyl)-2-(N-hexacosanoylamino) -1,3,4-octadecanetriol (KRN7000) on antigen-presenting function of antigen-presenting cells and antimetastatic activity of KRN7000-pretreated antigen-presenting cells. Oncology research 19960101
Characterization of neutral glycosphingolipids in rat lens. Experimental eye research 19950201
KRN7000, a novel immunomodulator, and its antitumor activities. Oncology research 19950101
Properties