Compounds > isoglobotrihexosylceramide
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isoglobotrihexosylceramide

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

isoglobotrihexosylceramide: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

N-hexacosanoylisoglobotriaosyl ceramide : The N-hexacosanoyl derivative of isoglobotriaosyl ceramide. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID5497158
CHEMBL ID413472
CHEBI ID73269
CHEBI ID73449
MeSH IDM0503876

Synonyms (16)

Synonym
isoglobotrihexosylceramide
hexacosanamide, n-[(1s,2r,3e)-1-[[[o-alpha-d-galactopyranosyl-(1->3)-o-beta-d-galactopyranosyl-(1->4)-beta-d-glucopyranosyl]oxy]methyl]-2-hydroxy-3-heptadecenyl]-
galalpha3galbeta4glcbeta1cer
gal alpha1,3 gal beta1,4 glc beta1,1 cer
n-((2s,3r,e)-1-(5-(3,5-dihydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yloxy)tetrahydro-2h-pyran-2-yloxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yloxy)-3-hydroxyoctadec-4-en-2-yl)hexaicosanamide
igb3
chebi:73269 ,
isoglobotrihexosyceramide
CHEMBL413472
n-[(2s,3r,4e)-1-{[alpha-d-galactopyranosyl-(1->3)-beta-d-galactopyranosyl-(1->4)-beta-d-glucopyranosyl]oxy}-3-hydroxyoctadec-4-en-2-yl]hexacosanamide
alpha-d-galactosyl-(1->3)-beta-d-galactosyl-(1->4)-beta-d-glucosyl-n-(hexacosanoyl)sphingosine
n-hexacosanoylisoglobotriaosyl ceramide
EPITOPE ID:191036
chebi:73449
EPITOPE ID:187230
Q27105008

Research Excerpts

Overview

Isoglobotrihexosylceramide (iGb3) is an immunomodulatory glycolipid that binds to CD1d. It is presented to the T-cell receptor (TCR) of invariant natural killer T (iNKT) cells.

ExcerptReferenceRelevance
"Isoglobotrihexosylceramide (iGb3, 1) is an immunomodulatory glycolipid that binds to CD1d and is presented to the T-cell receptor (TCR) of invariant natural killer T (iNKT) cells. "( A divergent approach to the synthesis of iGb3 sugar and lipid analogues via a lactosyl 2-azido-sphingosine intermediate.
Cheng, JM; Dangerfield, EM; Stocker, BL; Timmer, MS, 2014)		1.85
"Isoglobotrihexosylceramide (iGb3) is an endogenous antigen of mammalian cells and can stimulate invariant natural killer T (iNKT) cells to evoke autoimmune activities by the release of T helper 1 (Th1) and Th2 cytokines. "( Modification of the ceramide moiety of isoglobotrihexosylceramide on its agonist activity in stimulation of invariant natural killer T cells.
Chen, W; De Libero, G; Emmanuel, R; Schümann, J; Wang, PG; Xia, C; Zhang, W; Zhang, Y, 2007)		2.05

Effects

Isoglobotrihexosylceramide (iGb3) has been identified as a potent CD1d-presented self-antigen for mouse invariant natural killer T (iNKT) cells. It has been suggested to control overstimulation and deletion of iNKT cells in α-galactosidase A-deficient mice.

ExcerptReferenceRelevance
"Isoglobotrihexosylceramide (iGb3) has been implicated as this endogenous selecting ligand and recently suggested to control overstimulation and deletion of iNKT cells in α-galactosidase A-deficient (αGalA(-/-)) mice (human Fabry disease), which accumulate isoglobosides and globosides."( Globosides but not isoglobosides can impact the development of invariant NKT cells and their interaction with dendritic cells.
Bonrouhi, M; Cerundolo, V; Dyson, J; Gröne, HJ; Jennemann, R; Lehuen, A; Luckow, B; Malle, E; Müthing, J; Platt, FM; Porubsky, S; Salio, M; Singh, Y; Speak, AO; Zafarulla, R, 2012)		1.1
"Isoglobotrihexosylceramide (iGb3) has been identified as a potent CD1d-presented self-antigen for mouse invariant natural killer T (iNKT) cells. "( CD1d protein structure determines species-selective antigenicity of isoglobotrihexosylceramide (iGb3) to invariant NKT cells.
Brennan, PJ; Brenner, MB; Gadola, SD; Godfrey, DI; Kawahara, K; Lissin, N; Mansour, S; Matulis, G; Patel, O; Rossjohn, J; Sanderson, JP; Zähringer, U, 2013)		2.07
"Isoglobotrihexosylceramide (iGb3) has been identified as an endogenous ligand recognized by NKT cells; however, it is a weak agonist compared to the exogenous alpha-galactosylceramide. "( Chemical modification of iGb3 increases IFN-gamma production by hepatic NKT cells.
Chen, W; Han, Q; Shang, P; Tian, Z; Wang, PG; Xia, C; Zhang, C; Zhang, J, 2008)		1.79
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
antigenAny substance that stimulates an immune response in the body, such as through antibody production or by presentation to a T-cell receptor after binding to a major histocompability complex (MHC).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
alpha-D-Galp-(1->3)-beta-D-Galp-(1->4)-beta-D-Glcp-(1<->1')-CerA glycotriaosylceramide having alpha-D-galactosyl-(1->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl as the glycotriaosyl component.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID263700Release of IL2 from mouse iNKT hybridoma stimulated by bone marrow-derived mouse DC at 0.2 ug/ml2006Bioorganic & medicinal chemistry letters, Apr-15, Volume: 16, Issue:8
Synthesis and biological evaluation of alpha-galactosylceramide (KRN7000) and isoglobotrihexosylceramide (iGb3).
AID263699Release of IL4 and IFN-gamma from human iNKT cells stimulated by C1R cell expressing human CD1d at 20 ug/ml2006Bioorganic & medicinal chemistry letters, Apr-15, Volume: 16, Issue:8
Synthesis and biological evaluation of alpha-galactosylceramide (KRN7000) and isoglobotrihexosylceramide (iGb3).
AID263698Release of IL4 and IFN-gamma from human iNKT cells stimulated by C1R cell expressing human CD1d at 5 ug/ml2006Bioorganic & medicinal chemistry letters, Apr-15, Volume: 16, Issue:8
Synthesis and biological evaluation of alpha-galactosylceramide (KRN7000) and isoglobotrihexosylceramide (iGb3).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (28)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's15 (53.57)29.6817
2010's13 (46.43)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.02

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.02 (24.57)
Research Supply Index3.37 (2.92)
Research Growth Index4.39 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.02)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews4 (14.29%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other24 (85.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
inositol
Inositol: An isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1379) Inositol phospholipids are important in signal transduction.. inositol : Any cyclohexane-1,2,3,4,5,6-hexol.. 1D-chiro-inositol : Belonging to the inositol family of compounds, D-chiro-inositol (DCI) is an isomer of glucose. It is an important secondary messenger in insulin signal transduction.. muco-inositol : An inositol that is cyclohexane-1,2,3,4,5,6-hexol having a (1R,2R,3r,4R,5S,6r)-configuration.		2.0510cyclitol;
hexol
conduritol epoxide
conduritol epoxide: conduritol C epoxide refers to the (epi & neo)-isomers; structure. conduritol epoxide : An epoxide resulting from the epoxidation of the double bond of a conduritol.		2.0510cyclitol;
epoxide;
tetrol
lactose
Lactose: A disaccharide of GLUCOSE and GALACTOSE in human and cow milk. It is used in pharmacy for tablets, in medicine as a nutrient, and in industry.. lactose : A glycosylglucose disaccharide, found most notably in milk, that consists of D-galactose and D-glucose fragments bonded through a beta-1->4 glycosidic linkage. The glucose fragment can be in either the alpha- or beta-pyranose form, whereas the galactose fragment can only have the beta-pyranose form.. beta-lactose : The beta-anomer of lactose.		2.110lactose
uridine diphosphate galactose
Uridine Diphosphate Galactose: A nucleoside diphosphate sugar which can be epimerized into UDPglucose for entry into the mainstream of carbohydrate metabolism. Serves as a source of galactose in the synthesis of lipopolysaccharides, cerebrosides, and lactose.. UDP-alpha-D-galactose : A UDP-D-galactose in which the anomeric centre of the galactose moiety has alpha-configuration.		2.0510UDP-D-galactosemouse metabolite
1-deoxynojirimycin
1-deoxy-nojirimycin: structure in first source. duvoglustat : An optically active form of 2-(hydroxymethyl)piperidine-3,4,5-triol having 2R,3R,4R,5S-configuration.		2.03102-(hydroxymethyl)piperidine-3,4,5-triol;
piperidine alkaloid		anti-HIV agent;
anti-obesity agent;
bacterial metabolite;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
hepatoprotective agent;
hypoglycemic agent;
plant metabolite
miglustat
miglustat: a glucosylceramide synthase inhibitor. miglustat : A hydroxypiperidine that is deoxynojirimycin in which the amino hydrogen is replaced by a butyl group.		2.0310piperidines;
tertiary amino compound		anti-HIV agent;
EC 2.4.1.80 (ceramide glucosyltransferase) inhibitor
galactosyl-(1-3)galactose
galactosyl-(1-3)galactose: RN given refers to (alpha-D)-isomer		2.4920O-acyl carbohydrate
tretinoin
Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.		2.0510retinoic acid;
vitamin A		anti-inflammatory agent;
antineoplastic agent;
antioxidant;
AP-1 antagonist;
human metabolite;
keratolytic drug;
retinoic acid receptor agonist;
retinoid X receptor agonist;
signalling molecule
krn 7000
KRN 7000: has an alpha-galactosylceramide structure; structure given in first source. alpha-galactosylceramide : A galactosylceramide in which the galactosyl residue has alpha anomeric conofiguration.. 1-O-(alpha-D-galactosyl)-N-hexacosanoylphytosphingosine : A glycophytoceramide having an alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen.		4.0540glycophytoceramide;
N-acyl-beta-D-galactosylphytosphingosine		allergen;
antigen;
antineoplastic agent;
epitope;
immunological adjuvant
sphingosine
sphing-4-enine : A sphingenine in which the C=C double bond is located at the 4-position.. sphingenine : A 2-aminooctadecene-1,3-diol having (2S,3R)-configuration.. sphingoid : Sphinganine, its homologs and stereoisomers, and the hydroxy and unsaturated derivatives of these compounds.. 2-aminooctadec-4-ene-1,3-diol : A 2-aminooctadecene-1,3-diol having its double bond at position 4.		2.110sphing-4-eninehuman metabolite;
mouse metabolite
glycolipids
[no description available]		4.5640
globotriaosylceramide
globotriaosylceramide: receptor for Shigella. alpha-D-galactosyl-(1->4)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide : A glycotriaosylceramide having alpha-D-galactosyl-(1->4)-beta-D-galactosyl-(1->4)-beta-D-glucosyl component attached to the primary hydroxy function of a ceramide with undefined sphingoid base.		2.0310
ConditionIndicatedRelationship StrengthStudiesTrials
Esophageal Reflux
[description not available]		02.0410
Gastroesophageal Reflux
Retrograde flow of gastric juice (GASTRIC ACID) and/or duodenal contents (BILE ACIDS; PANCREATIC JUICE) into the distal ESOPHAGUS, commonly due to incompetence of the LOWER ESOPHAGEAL SPHINCTER.		02.0410
Chronic Illness
[description not available]		02.0510
Acid beta-Glucosidase Deficiency
[description not available]		02.0510
Innate Inflammatory Response
[description not available]		02.4620
Chronic Disease
Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).		02.0510
Gaucher Disease
An autosomal recessive disorder caused by a deficiency of acid beta-glucosidase (GLUCOSYLCERAMIDASE) leading to intralysosomal accumulation of glycosylceramide mainly in cells of the MONONUCLEAR PHAGOCYTE SYSTEM. The characteristic Gaucher cells, glycosphingolipid-filled HISTIOCYTES, displace normal cells in BONE MARROW and visceral organs causing skeletal deterioration, hepatosplenomegaly, and organ dysfunction. There are several subtypes based on the presence and severity of neurological involvement.		02.0510
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.4620
Blood Poisoning
[description not available]		02.0510
Bacterial Infections, Gram-Negative
[description not available]		03.3620
Gram-Negative Bacterial Infections
Infections caused by bacteria that show up as pink (negative) when treated by the gram-staining method.		03.3620
Sepsis
Systemic inflammatory response syndrome with a proven or suspected infectious etiology. When sepsis is associated with organ dysfunction distant from the site of infection, it is called severe sepsis. When sepsis is accompanied by HYPOTENSION despite adequate fluid infusion, it is called SEPTIC SHOCK.		02.0510
B16 Melanoma
[description not available]		02.0610
Metastase
[description not available]		02.0610
Neoplasm Metastasis
The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.		02.0610
Lysosomal Enzyme Disorders
[description not available]		02.9410
Lipid Metabolism Disorders
Pathological conditions resulting from abnormal anabolism or catabolism of lipids in the body.		02.0310
Autoimmune Disease
[description not available]		02.9510
Autoimmune Diseases
Disorders that are characterized by the production of antibodies that react with host tissues or immune effector cells that are autoreactive to endogenous peptides.		02.9510