staphyloxanthin (CHEBI:71690)

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CHEBI:71690 - staphyloxanthin

ChEBI ID	CHEBI:71690
ChEBI Name	staphyloxanthin
Stars
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.
Last Modified	30 December 2017
Submitter	Gareth Owen
Downloads	Molfile

Formula	C51H78O8
Net Charge	0
Average Mass	819.177
Monoisotopic Mass	818.56967
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
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

Wikipedia

Roles Classification

Chemical Role:

antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.

Biological Roles:

biological pigment An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light.

metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.

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 ester	ChemIDplus
β-D-glucopyranosyl 1-O-(4,4'-diaponeurosporen-4-oate)-6-O-(12-methyltetradecanoate)	MetaCyc

UniProt Name	Source
staphyloxanthin	UniProt

Manual Xrefs	Databases
C16148	KEGG COMPOUND
Staphyloxanthin	Wikipedia
CPD-9916	MetaCyc

Registry Numbers	Sources
Reaxys:22781667	Reaxys
CAS:71869-01-7	ChemIDplus
CAS:71869-01-7	KEGG COMPOUND

Citations