Structure Database (LMSD)

Common Name
Lutein
Systematic Name
(3R,3'R,6'R)-β,ε-Carotene-3,3'-diol
Synonyms
LM ID
LMPR01070274
Formula
Exact Mass
Calculate m/z
568.42803
Status
Curated



Classification

Biological Context

Lutein is a dietary carotenoid that has been found in eggs and yellow-colored fruits and vegetables and has diverse biological activities.1,2,3,4 It reduces hyperglycemia-induced mitochondrial DNA damage and production of reactive oxygen species (ROS) and promotes mitochondrial biogenesis in ARPE-19 cells when used at a concentration of 10 µM.1 Lutein (20 mg/kg) increases nitric oxide (NO) production and decreases serum levels of endothelin-1 in a rat model of hyperhomocysteinemia.2 Dietary administration of lutein (0.2%) decreases monocyte migration and lesion size in an ApoE-/- and Ldlr-/- mouse models of atherosclerosis. Lutein reduces infarct size and cardiac malondialdehyde (MDA), lactate dehydrogenase (LDH), and troponin T levels, and increases cardiac levels of catalase (CAT), superoxide dismutase (SOD), heme oxygenase-1 (HO-1), and Nrf2 in a rat model of heart failure induced by isoproterenol .3 It forms a retinal pigment in human eyes, and high dietary intake of lutein is positively correlated with reduced risk of age-related macular degeneration and cataracts in humans.4

This information has been provided by Cayman Chemical

References

4. Bungau, S., Abdel-Daim, M., Tit, D.M., et al. Health benefits of polyphenols and carotenoids in age-related eye diseases. Oxid. Med. Cell. Longev. 9783429 (2019).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Micrococcus luteus (#1270)
Actinomycetes (#1760)
Lutein in a bacterial membrane.,
Nature, 1958
Pubmed ID: 13566177
Calendula officinalis (#41496)
Magnoliopsida (#3398)
Studies in carotenogenesis. 13. The carotenoids of the flower petals of Calendula officinalis.,
Biochem J, 1954
Pubmed ID: 13198857

String Representations

InChiKey (Click to copy)
KBPHJBAIARWVSC-RGZFRNHPSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
[C@H]1(/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C2=C(C)C[C@@H](O)CC2(C)C)C(C)=C[C@H](O)CC1(C)C

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
Carotenoid ID
PDB ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 42
Rings 2
Aromatic Rings 0
Rotatable Bonds 10
Van der Waals Molecular Volume 664.38
Topological Polar Surface Area 40.46
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 2
logP 10.98
Molar Refractivity 185.13

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Created at
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Updated at
20th Nov 2024