ALPHA-GALACTOSYLCERAMIDE

Investigational

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 Search

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

Molecular Formula	C50H99NO9
Molecular Weight	858.3224
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8866665 | https://www.ncbi.nlm.nih.gov/pubmed/10594688

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.

Originator

Approval Year

PubMed

Title	Date	PubMed
Characterization of neutral glycosphingolipids in rat lens.	1995 Feb	7781748
NK T cell activation promotes Chlamydia trachomatis infection in vivo.	2005 Sep 1	16116210
The CD1d-binding glycolipid alpha-galactosylceramide enhances humoral immunity to T-dependent and T-independent antigen in a CD1d-dependent manner.	2006 Sep	16792697
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	19587013
Differential recognition of CD1d-alpha-galactosyl ceramide by the V beta 8.2 and V beta 7 semi-invariant NKT T cell receptors.	2009 Jul 17	19592275
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	20123711
A CD1d-dependent antagonist inhibits the activation of invariant NKT cells and prevents development of allergen-induced airway hyperreactivity.	2010 Feb 15	20083656
PD-L1 and PD-L2 modulate airway inflammation and iNKT-cell-dependent airway hyperreactivity in opposing directions.	2010 Jan	19741598
Lipid binding orientation within CD1d affects recognition of Borrelia burgorferi antigens by NKT cells.	2010 Jan 26	20080535
Dietary fatty acids modulate antigen presentation to hepatic NKT cells in nonalcoholic fatty liver disease.	2010 Jul	20185414
Slam haplotypes modulate the response to lipopolysaccharide in vivo through control of NKT cell number and function.	2010 Jul 1	20530260
Plasticity of invariant NKT cell regulation of allergic airway disease is dependent on IFN-gamma production.	2010 Jul 1	20525882
Development of spontaneous anergy in invariant natural killer T cells in a mouse model of dyslipidemia.	2010 Sep	20539017
Recognition of β-linked self glycolipids mediated by natural killer T cell antigen receptors.	2011 Jul 31	21804559
Cutting edge: structural basis for the recognition of β-linked glycolipid antigens by invariant NKT cells.	2011 Sep 1	21810611
Invariant natural killer T cells recognize glycolipids from pathogenic Gram-positive bacteria.	2011 Sep 4	21892173
Activation of Invariant NKT cells with glycolipid ligand α-galactosylceramide ameliorates glucose-6-phosphate isomerase peptide-induced arthritis.	2012	23251456
The molecular basis for recognition of CD1d/α-galactosylceramide by a human non-Vα24 T cell receptor.	2012	23109910
Lysophospholipid presentation by CD1d and recognition by a human Natural Killer T-cell receptor.	2012 Apr 18	22395072
Structural basis for the recognition of C20:2-αGalCer by the invariant natural killer T cell receptor-like antibody L363.	2012 Jan 6	22110136
Structural and functional characterization of a novel nonglycosidic type I NKT agonist with immunomodulatory properties.	2012 Mar 1	22301545
Human and mouse type I natural killer T cell antigen receptors exhibit different fine specificities for CD1d-antigen complex.	2012 Nov 9	22995911
Type II natural killer T cells use features of both innate-like and conventional T cells to recognize sulfatide self antigens.	2012 Sep	22820602
Lack of PD-L1 expression by iNKT cells improves the course of influenza A infection.	2013	23555047
Slam haplotype 2 promotes NKT but suppresses Vγ4+ T-cell activation in coxsackievirus B3 infection leading to increased liver damage but reduced myocarditis.	2013 Feb	23195432
Recognition of microbial and mammalian phospholipid antigens by NKT cells with diverse TCRs.	2013 Jan 29	23307809
Bacterial CD1d-restricted glycolipids induce IL-10 production by human regulatory T cells upon cross-talk with invariant NKT cells.	2013 Sep 1	23898038
Enhanced TCR footprint by a novel glycolipid increases NKT-dependent tumor protection.	2013 Sep 15	23960235
Chronic alcohol consumption enhances iNKT cell maturation and activation.	2015 Jan 15	25499027

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:46:44 GMT 2023` Edited by `admin` on `Fri Dec 15 15:46:44 GMT 2023`
Record UNII	WX671898JF
Record Status	`Validated (UNII)`
Record Version

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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