lutein   Click here for help

GtoPdb Ligand ID: 13099

Synonyms: E 161b | xanthophyll
Compound class: Natural product or derivative
Comment: Lutein is a carotenoid that derives from plants including Eupatorium cannabinum (hemp agrimony), Hibiscus syriacus (rose of Sharon) and green leafy vegetables such as spinach and kale. It is a commercially used food additive and dietary supplement.
In humans ingested lutein is accumulated in the macula (central retina), where it is a component of the macular pigment (a blue light filter and antioxidant) that is important for optimal visual acuity [1]. Its use is permitted in many jurisdictions as a safe ingredient for inclusion in food supplements that claim to maintain eye health and visual performance, although clinical benefit has not been robustly established.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 40.46
Molecular weight 568.87
XLogP 11.28
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES C/C(=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)C[C@H](CC1(C)C)O)/C=C/C=C(\C)/C=C/[C@H]2C(=C[C@@H](CC2(C)C)O)C
Isomeric SMILES CC1=C(C(C[C@@H](C1)O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/[C@H]2C(=C[C@@H](CC2(C)C)O)C)/C)/C
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
InChI Key KBPHJBAIARWVSC-RGZFRNHPSA-N
Classification Click here for help
Compound class Natural product or derivative
IUPAC Name Click here for help
(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethylcyclohex-3-en-1-ol
Synonyms Click here for help
E 161b | xanthophyll
Database Links Click here for help
ChEBI CHEBI:28838
ChEMBL Ligand CHEMBL173929
DrugBank Ligand DB00137
GtoPdb PubChem SID 491299881
PubChem CID 5281243
Search Google for chemical match using the InChIKey KBPHJBAIARWVSC-RGZFRNHPSA-N
Search Google for chemicals with the same backbone KBPHJBAIARWVSC
UniChem Compound Search for chemical match using the InChIKey KBPHJBAIARWVSC-RGZFRNHPSA-N
UniChem Connectivity Search for chemical match using the InChIKey KBPHJBAIARWVSC-RGZFRNHPSA-N