IMPPAT Phytochemical information: 
Lutein
Lutein
Summary

SMILES: C/C(=CC=CC=C(C=CC=C(C=CC1=C(C)C[C@H](CC1(C)C)O)/C)/C)/C=C/C=C(/C=C/[C@H]1C(=C[C@@H](CC1(C)C)O)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
InChIKey: KBPHJBAIARWVSC-RGZFRNHPSA-N
DeepSMILES: C/C=CC=CC=CC=CC=CC=CC=CC)C[C@H]CC6C)C)))O)))))))/C)))))/C))))))/C=C/C=C/C=C/[C@H]C=C[C@@H]CC6C)C)))O)))C)))))C
Scaffold Graph/Node/Bond level: C(=CC=CC=CC=CC=CC1C=CCCC1)C=CC=CC=CC=CC1=CCCCC1
Scaffold Graph/Node level: C(CCCCCCCCCC1CCCCC1)CCCCCCCCC1CCCCC1
Scaffold Graph level: C(CCCCCCCCCC1CCCCC1)CCCCCCCCC1CCCCC1
Functional groups: CC(C)=C(C)/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C; CC(C)=CC; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Tetraterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Carotenoids (C40)
NP Classifier Class: Carotenoids (C40, β-ε)
Synonymous chemical names:
3-epilutein, lutein, luteine, xanthophyll, xanthophylls, xanthopyll
External chemical identifiers:
CID:5281243; ChEMBL:CHEMBL173929; ChEBI:28838; ZINC:ZINC000008221225; FDASRS:X72A60C9MT; SureChEMBL:SCHEMBL19342; MolPort-023-220-417
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Lutein
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 568.89
Log P RDKit 10.4
Topological polar surface area (Å2) RDKit 40.46
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 40
Number of heavy atoms RDKit 42
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.07
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 22
Number of sp3 hybridized carbon atoms RDKit 18
Shape complexity RDKit 0.45
Number of rotatable bonds RDKit 10
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
Lutein
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 4
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.2032
Lutein
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.0
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 0.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes
Lutein
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000258168BCMO1871
ENSP00000262209TRPA1800
ENSP00000262735PPARA821
ENSP00000262999UCP1819
ENSP00000263233SYP800
ENSP00000322788MMP1800
ENSP00000361405MMP9814
ENSP00000414303BDNF800
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.