CHEBI:71690 - staphyloxanthin

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ChEBI Name staphyloxanthin
ChEBI ID CHEBI:71690
Definition A xanthophyll that is β-D-glucopyranose in which the hydroxy groups at positions 1 and 6 have been acylated by an all-trans-2,6,10,15,19,23-hexamethyltetracosa-2,4,6,8,10,12,14,16,18,22-decaenoyl group and a 12-methyltetradecanoyl group, respectively. Staphyloxanthin is responsible for the characteristic yellow-golden colour which gives the bacterium Staphylococcus aureus its name.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C51H78O8
Net Charge 0
Average Mass 819.16020
Monoisotopic Mass 818.570
InChI InChI=1S/C51H78O8/c1-10-39(4)26-17-15-13-11-12-14-16-18-36-46(52)57-37-45-47(53)48(54)49(55)51(58-45)59-50(56)44(9)35-24-34-43(8)33-23-31-41(6)28-20-19-27-40(5)30-22-32-42(7)29-21-25-38(2)3/h19-20,22-25,27-28,30-35,39,45,47-49,51,53-55H,10-18,21,26,29,36-37H2,1-9H3/b20-19+,30-22+,31-23+,34-24+,40-27+,41-28+,42-32+,43-33+,44-35+/t39?,45-,47-,48+,49-,51+/m1/s1
InChIKey PDOUICUKTQRPHO-MENSNCDRSA-N
SMILES CCC(C)CCCCCCCCCCC(=O)OC[C@H]1O[C@@H](OC(=O)C(\C)=C\C=C\C(C)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(/C)CCC=C(C)C)[C@H](O)[C@@H](O)[C@@H]1O
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s): biological pigment
An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light.
virulence factor
Any toxin secreted by bacteria, viruses, fungi or protozoa enabling them to achieve colonisation of a niche in the host, inhibit or evade the host's immune response, enter and exit cells, or obtain nutrition from the host.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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ChEBI Ontology
Outgoing staphyloxanthin (CHEBI:71690) has functional parent β-D-glucose (CHEBI:15903)
staphyloxanthin (CHEBI:71690) has functional parent anteisopentadecanoic acid (CHEBI:39251)
staphyloxanthin (CHEBI:71690) has role antioxidant (CHEBI:22586)
staphyloxanthin (CHEBI:71690) has role biological pigment (CHEBI:26130)
staphyloxanthin (CHEBI:71690) has role metabolite (CHEBI:25212)
staphyloxanthin (CHEBI:71690) has role virulence factor (CHEBI:72316)
staphyloxanthin (CHEBI:71690) is a D-aldohexose derivative (CHEBI:63387)
staphyloxanthin (CHEBI:71690) is a apo carotenoid triterpenoid (CHEBI:36783)
staphyloxanthin (CHEBI:71690) is a fatty acid ester (CHEBI:35748)
staphyloxanthin (CHEBI:71690) is a triol (CHEBI:27136)
staphyloxanthin (CHEBI:71690) is a xanthophyll (CHEBI:27325)
IUPAC Name
1-O-[(2E,4E,6E,8E,10E,12E,14E,16E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,4,6,8,10,12,14,16,18,22-decaenoyl]-6-O-(12-methyltetradecanoyl)-β-D-glucopyranose
Synonyms Sources
8'-apo-ψ,ψ-carotenoic acid, 6-O-(12-methyl-1-oxotetradecyl)-α-D-glucopyranosyl ester ChemIDplus
β-D-glucopyranosyl 1-O-(4,4'-diaponeurosporen-4-oate)-6-O-(12-methyltetradecanoate) MetaCyc
staphyloxanthin UniProt
Database Links Databases
C16148 KEGG COMPOUND
CPD-9916 MetaCyc
Staphyloxanthin Wikipedia
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Registry Numbers Types Sources
22781667 Reaxys Registry Number Reaxys
71869-01-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
16009720 PubMed citation Europe PMC
16020541 PubMed citation Europe PMC
16861688 PubMed citation Europe PMC
18276850 PubMed citation Europe PMC
19456099 PubMed citation Europe PMC
22223336 PubMed citation Europe PMC
22535955 PubMed citation Europe PMC
22965624 PubMed citation Europe PMC
7275936 PubMed citation Europe PMC
Last Modified
30 December 2017
General Comment
2013-02-08 Note that the original assignment of an α-D-glucopyranosyl configuration made by John H. Marshall and Gregory J. Wilmoth in J. Bacteriol., 1981, 147(3), 900-913 was subsequently corrected to a β-D-glucopyranosyl configuration by Friedrich Götz et al., J. Biol. Chem., 2005, 280(37), 32493-32498.