CHEBI:28838 - lutein

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name lutein
ChEBI ID CHEBI:28838
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:43817, CHEBI:6576, CHEBI:27324
Supplier Information ChemicalBook:CB2149336, eMolecules:518373
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Homocysteine (; symbol Hcy) is a non-proteinogenic α-amino acid. It is a homologue of the amino acid cysteine, differing by an additional methylene bridge (−CH2−). It is biosynthesized from methionine by the removal of its terminal Cε methyl group. In the body, homocysteine can be recycled into methionine or converted into cysteine with the aid of vitamin B6, B9, and B12. High levels of homocysteine in the blood (hyperhomocysteinemia) is regarded as a marker of cardiovascular disease, likely working through atherogenesis, which can result in ischemic injury. Therefore, hyperhomocysteinemia is a possible risk factor for coronary artery disease. Coronary artery disease occurs when an atherosclerotic plaque blocks blood flow to the coronary arteries, which supply the heart with oxygenated blood. Hyperhomocysteinemia has been correlated with the occurrence of blood clots, heart attacks, and strokes, although it is unclear whether hyperhomocysteinemia is an independent risk factor for these conditions. Hyperhomocysteinemia has also been associated with early-term spontaneous abortions and with neural tube defects.
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Formula C40H56O2
Net Charge 0
Average Mass 568.87144
Monoisotopic Mass 568.42803
InChI InChI=1S/C40H56O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-25,35-37,41-42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36+,37-/m0/s1
InChIKey KBPHJBAIARWVSC-RGZFRNHPSA-N
SMILES CC(\C=C\C=C(C)\C=C\[C@H]1C(C)=C[C@H](O)CC1(C)C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C
Roles Classification
Biological Role(s): food colouring
A food additive that imparts colour to food. In European countries, E-numbers for permitted food colours are from E 100 to E 199, divided into yellows (E 100-109), oranges (E 110-119), reds (E 120-129), blues and violets (E 130-139), greens (E 140-149), browns and blacks (E 150-159), and others (E 160-199).
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): food colouring
A food additive that imparts colour to food. In European countries, E-numbers for permitted food colours are from E 100 to E 199, divided into yellows (E 100-109), oranges (E 110-119), reds (E 120-129), blues and violets (E 130-139), greens (E 140-149), browns and blacks (E 150-159), and others (E 160-199).
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ChEBI Ontology
Outgoing lutein (CHEBI:28838) has parent hydride (6'R)-β,ε-carotene (CHEBI:35147)
lutein (CHEBI:28838) has role food colouring (CHEBI:77182)
lutein (CHEBI:28838) has role plant metabolite (CHEBI:76924)
lutein (CHEBI:28838) is a carotenol (CHEBI:23045)
Incoming lutein 5,6-epoxide (CHEBI:27448) has functional parent lutein (CHEBI:28838)
IUPAC Name
(3R,3'R,6'R)-β,ε-carotene-3,3'-diol
Synonyms Sources
(3R,3'R,6S)-4,5-DIDEHYDRO-5,6-DIHYDRO-BETA,BETA-CAROTENE-3,3'-DIOL PDBeChem
Bo-Xan ChemIDplus
E 161b ChEBI
Lutein KEGG COMPOUND
lutein UniProt
Xanthophyll KEGG COMPOUND
Manual Xrefs Databases
4145 DrugCentral
C00003776 KNApSAcK
C08601 KEGG COMPOUND
CPD1F-119 MetaCyc
DB00137 DrugBank
HMDB0003233 HMDB
LMPR01070274 LIPID MAPS
LUT PDBeChem
Lutein Wikipedia
View more database links
Registry Numbers Types Sources
127-40-2 CAS Registry Number KEGG COMPOUND
127-40-2 CAS Registry Number ChemIDplus
2068550 Reaxys Registry Number Reaxys
Citations Types Sources
10714278 PubMed citation Europe PMC
14670087 PubMed citation Europe PMC
23543147 PubMed citation Europe PMC
24451312 PubMed citation Europe PMC
Last Modified
22 February 2017