(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R)-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
PubChem CID: 6433159
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| Compound Synonyms | SCHEMBL14439445 |
|---|---|
| Topological Polar Surface Area | 40.5 |
| Hydrogen Bond Donor Count | 2.0 |
| Heavy Atom Count | 42.0 |
| Description | Lutein, also known as all-trans-lutein or 3,3'-dihydroxy-alpha-carotene, is a member of the class of compounds known as xanthophylls. Xanthophylls are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. Lutein is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Lutein can be found in dandelion and ginkgo nuts, which makes lutein a potential biomarker for the consumption of these food products. Lutein can be found primarily in blood, as well as throughout most human tissues. Lutein exists in all eukaryotes, ranging from yeast to humans. Lutein is isomeric with zeaxanthin, differing only in the placement of one double bond. Lutein and zeaxanthin can be interconverted in the body through an intermediate called meso-zeaxanthin. The principal natural stereoisomer of lutein is (3R,3′R,6′R)-beta,epsilon-carotene-3,3′-diol. Lutein is a lipophilic molecule and is generally insoluble in water. The presence of the long chromophore of conjugated double bonds (polyene chain) provides the distinctive light-absorbing properties. The polyene chain is susceptible to oxidative degradation by light or heat and is chemically unstable in acids . |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 1270.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 2.0 |
| Iupac Name | (1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R)-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 |
| Prediction Hob | 0.0 |
| Class | Prenol lipids |
| Xlogp | 11.0 |
| Superclass | Lipids and lipid-like molecules |
| Subclass | Tetraterpenoids |
| Molecular Formula | C40H56O2 |
| Prediction Swissadme | 0.0 |
| Inchi Key | KBPHJBAIARWVSC-RTIVXWJOSA-N |
| Fcsp3 | 0.45 |
| Logs | -4.556 |
| Rotatable Bond Count | 10.0 |
| Logd | 4.555 |
| Synonyms | 3,3'-Dihydroxy-alpha-carotene, all-trans-(+)-Xanthophyll, all-trans-Lutein, beta,epsilon-Carotene-3,3'-diol, bo-Xan, Lutein ester, Luteine, trans-Lutein, Vegetable lutein, Vegetable luteol, Lutein F, Lutein g, Lutein, gamma, gamma Lutein |
| Compound Name | (1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R)-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 |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 568.428 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 568.428 |
| Hydrogen Bond Acceptor Count | 2.0 |
| Molecular Weight | 568.9 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 3.0 |
| Total Bond Stereocenter Count | 9.0 |
| Molecular Framework | Aliphatic homomonocyclic compounds |
| Esol | -9.643393200000002 |
| 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+/m1/s1 |
| 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(=CC(CC2(C)C)O)C)/C)/C |
| Nring | 2.0 |
| Defined Bond Stereocenter Count | 9.0 |
| Taxonomy Direct Parent | Xanthophylls |
- 1. Outgoing r'ship
FOUND_INto/from Capsicum Annuum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 2. Outgoing r'ship
FOUND_INto/from Citrus Aurantium (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 3. Outgoing r'ship
FOUND_INto/from Citrus Natsudaidai (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 4. Outgoing r'ship
FOUND_INto/from Citrus Sinensis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 5. Outgoing r'ship
FOUND_INto/from Citrus Trifoliata (Plant) Rel Props:Source_db:cmaup_ingredients - 6. Outgoing r'ship
FOUND_INto/from Ginkgo Biloba (Plant) Rel Props:Source_db:fooddb_chem_all - 7. Outgoing r'ship
FOUND_INto/from Hippophae Rhamnoides (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 8. Outgoing r'ship
FOUND_INto/from Lycium Barbarum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 9. Outgoing r'ship
FOUND_INto/from Lycium Chinense (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 10. Outgoing r'ship
FOUND_INto/from Perilla Frutescens (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all - 11. Outgoing r'ship
FOUND_INto/from Taraxacum Officinale (Plant) Rel Props:Source_db:fooddb_chem_all - 12. Outgoing r'ship
FOUND_INto/from Zostera Marina (Plant) Rel Props:Source_db:npass_chem_all