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Details

Stereochemistry ABSOLUTE
Molecular Formula C50H99NO9
Molecular Weight 858.3224
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALPHA-GALACTOSYLCERAMIDE

SMILES

CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@H](O)CCCCCCCCCCCCCC

InChI

InChIKey=VQFKFAKEUMHBLV-BYSUZVQFSA-N
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

HIDE SMILES / InChI
KRN-7000, a compound with an alpha-galactosylceramide structure, shows potent anti-tumor activity in animal models. It also has strong immunostimulating effect being a high-affinity CD1d antigen.

Approval Year

PubMed

PubMed

TitleDatePubMed
Characterization of neutral glycosphingolipids in rat lens.
1995 Feb
The crystal structure of human CD1d with and without alpha-galactosylceramide.
2005 Aug
Sustained expansion of NKT cells and antigen-specific T cells after injection of alpha-galactosyl-ceramide loaded mature dendritic cells in cancer patients.
2005 May 2
Design of natural killer T cell activators: structure and function of a microbial glycosphingolipid bound to mouse CD1d.
2006 Mar 14
Skin and peripheral lymph node invariant NKT cells are mainly retinoic acid receptor-related orphan receptor (gamma)t+ and respond preferentially under inflammatory conditions.
2009 Aug 1
Bacillus anthracis lethal toxin disrupts TCR signaling in CD1d-restricted NKT cells leading to functional anergy.
2009 Sep
CD1d-dependent B-cell help by NK-like T cells leads to enhanced and sustained production of Bacillus anthracis lethal toxin-neutralizing antibodies.
2010 Apr
Invariant NKT cells are required for antitumor responses induced by host-versus-graft responses.
2010 Aug 15
A CD1d-dependent antagonist inhibits the activation of invariant NKT cells and prevents development of allergen-induced airway hyperreactivity.
2010 Feb 15
Lipid binding orientation within CD1d affects recognition of Borrelia burgorferi antigens by NKT cells.
2010 Jan 26
Activation of Invariant NKT cells with glycolipid ligand α-galactosylceramide ameliorates glucose-6-phosphate isomerase peptide-induced arthritis.
2012
Crystal structures of bovine CD1d reveal altered αGalCer presentation and a restricted A' pocket unable to bind long-chain glycolipids.
2012
Structural and functional characterization of a novel nonglycosidic type I NKT agonist with immunomodulatory properties.
2012 Mar 1
Bacterial species-characteristic profiles of molecular species, and the antigenicity of phospholipids and glycolipids in symbiotic Lactobacillus, Staphylococcus and Streptococcus species.
2012 May
Key role for respiratory CD103(+) dendritic cells, IFN-γ, and IL-17 in protection against Streptococcus pneumoniae infection in response to α-galactosylceramide.
2012 Sep 1
Lack of PD-L1 expression by iNKT cells improves the course of influenza A infection.
2013
Recognition of microbial and mammalian phospholipid antigens by NKT cells with diverse TCRs.
2013 Jan 29
Bacterial CD1d-restricted glycolipids induce IL-10 production by human regulatory T cells upon cross-talk with invariant NKT cells.
2013 Sep 1
Enhanced TCR footprint by a novel glycolipid increases NKT-dependent tumor protection.
2013 Sep 15
Chronic alcohol consumption enhances iNKT cell maturation and activation.
2015 Jan 15
Patents

Patents

Name Type Language
ALPHA-GALACTOSYLCERAMIDE
Common Name English
KRN7000
Code English
.ALPHA.-GALCER
Common Name English
KRN-7000
Code English
HEXACOSANAMIDE, N-((1S,2S,3R)-1-((.ALPHA.-D-GALACTOPYRANOSYLOXY)METHYL)-2,3-DIHYDROXYHEPTADECYL)-
Systematic Name English
RGI-7000
Code English
Code System Code Type Description
PUBCHEM
2826713
Created by admin on Fri Dec 15 15:46:44 GMT 2023 , Edited by admin on Fri Dec 15 15:46:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID40935847
Created by admin on Fri Dec 15 15:46:44 GMT 2023 , Edited by admin on Fri Dec 15 15:46:44 GMT 2023
PRIMARY
NCI_THESAURUS
C1720
Created by admin on Fri Dec 15 15:46:44 GMT 2023 , Edited by admin on Fri Dec 15 15:46:44 GMT 2023
PRIMARY
FDA UNII
WX671898JF
Created by admin on Fri Dec 15 15:46:44 GMT 2023 , Edited by admin on Fri Dec 15 15:46:44 GMT 2023
PRIMARY
DRUG BANK
DB12232
Created by admin on Fri Dec 15 15:46:44 GMT 2023 , Edited by admin on Fri Dec 15 15:46:44 GMT 2023
PRIMARY
CAS
158021-47-7
Created by admin on Fri Dec 15 15:46:44 GMT 2023 , Edited by admin on Fri Dec 15 15:46:44 GMT 2023
PRIMARY