CHEBI:466659 - 1-O-(α-D-galactosyl)-N-hexacosanoylphytosphingosine

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ChEBI Name 1-O-(α-D-galactosyl)-N-hexacosanoylphytosphingosine
ChEBI ID CHEBI:466659
ChEBI ASCII Name 1-O-(alpha-D-galactosyl)-N-hexacosanoylphytosphingosine
Definition A glycophytoceramide having an α-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:40662
Supplier Information
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Formula C50H99NO9
Net Charge 0
Average Mass 858.32240
Monoisotopic Mass 857.73198
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
InChIKey VQFKFAKEUMHBLV-BYSUZVQFSA-N
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
Roles Classification
Biological Role(s): immunological adjuvant
A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.
antigen
Any 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).
epitope
The biological role played by a material entity when bound by a receptor of the adaptive immune system. Specific site on an antigen to which an antibody binds.
allergen
A chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
(via N-acylphytosphingosine )
Application(s): immunological adjuvant
A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 1-O-(α-D-galactosyl)-N-hexacosanoylphytosphingosine (CHEBI:466659) has functional parent α-D-galactose (CHEBI:28061)
1-O-(α-D-galactosyl)-N-hexacosanoylphytosphingosine (CHEBI:466659) has role allergen (CHEBI:50904)
1-O-(α-D-galactosyl)-N-hexacosanoylphytosphingosine (CHEBI:466659) has role antigen (CHEBI:59132)
1-O-(α-D-galactosyl)-N-hexacosanoylphytosphingosine (CHEBI:466659) has role antineoplastic agent (CHEBI:35610)
1-O-(α-D-galactosyl)-N-hexacosanoylphytosphingosine (CHEBI:466659) has role epitope (CHEBI:53000)
1-O-(α-D-galactosyl)-N-hexacosanoylphytosphingosine (CHEBI:466659) has role immunological adjuvant (CHEBI:50847)
1-O-(α-D-galactosyl)-N-hexacosanoylphytosphingosine (CHEBI:466659) is a glycophytoceramide (CHEBI:59389)
Incoming N-[(2S,3S,4R)-1-(α-D-galactosyloxy)-3,4-dihydroxyoctadecan-2-yl]hexacosanethioamide (CHEBI:86510) has functional parent 1-O-(α-D-galactosyl)-N-hexacosanoylphytosphingosine (CHEBI:466659)
IUPAC Name
N-[(2S,3S,4R)-1-(α-D-galactopyranosyloxy)-3,4-dihydroxyoctadecan-2-yl]hexacosanamide
Synonyms Sources
(2S,3S,4R)-1-O-(α-D-galactosyl)-N-hexacosanoyl-2-amino-1,3,4-octadecanetriol ChEBI
1-O-(α-D-galactopyranosyl)-N-hexacosanoylphytosphingosine ChEBI
α-GalCer ChEBI
α-GalCer(t18:0/26:0) ChEBI
α-GC (C26) ChEBI
α-GC(C26) ChEBI
Galα-Cer(t18:0/26:0) ChEBI
KRN 7000 ChemIDplus
Manual Xrefs Databases
1ZT4 PDB
2PO6 PDB
AGH PDBeChem
CA2683681 Patent
View more database links
Registry Numbers Types Sources
158021-47-7 CAS Registry Number ChemIDplus
7326597 Reaxys Registry Number Reaxys
7326597 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
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Last Modified
08 March 2019