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CHEBI:71690 - staphyloxanthin

Default Structure
ChEBI IDCHEBI:71690
ChEBI Namestaphyloxanthin
Stars
DefinitionA 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.
Last Modified30 December 2017
SubmitterGareth Owen
DownloadsMolfile
FormulaC51H78O8
Net Charge0
Average Mass819.177
Monoisotopic Mass818.56967
SMILESCCC(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
InChIInChI=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
InChIKeyPDOUICUKTQRPHO-MENSNCDRSA-N
Wikipedia
Roles Classification
Chemical Role:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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.
ChEBI Ontology
Outgoing Relation(s)
staphyloxanthin (CHEBI:71690) has functional parent 12-methyltetradecanoic acid (CHEBI:39251)
staphyloxanthin (CHEBI:71690) has functional parent β-D-glucose (CHEBI:15903)
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  Source
8'-apo-ψ,ψ-carotenoic acid, 6-O-(12-methyl-1-oxotetradecyl)-α-D-glucopyranosyl esterChemIDplus
β-D-glucopyranosyl 1-O-(4,4'-diaponeurosporen-4-oate)-6-O-(12-methyltetradecanoate)MetaCyc
UniProt Name  Source
staphyloxanthinUniProt
Manual XrefsDatabases
C16148KEGG COMPOUND
CPD-9916MetaCyc
StaphyloxanthinWikipedia
Registry NumbersSources
Reaxys:22781667Reaxys
CAS:71869-01-7ChemIDplus
CAS:71869-01-7KEGG COMPOUND
Citations