Lutein

  • GreenMolBD CID : 1839
  • Molecular Formula : C40H56O2
  • Molecular Weight : 568.886
  • Exact Molecular Mass : 568.428
  • IUPAC Name : (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
  • 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
  • Canonical SMILES : CC1=C(C(CC(C1)O)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC2C(=CC(CC2(C)C)O)C)C)C
  • Isomeric SMILES : CC1=C(C(CC(C1)O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C2C(=CC(CC2(C)C)O)C)/C)/C
  • Cross Reference  Pubchem

1. Classification

1.1. Description

This compound belongs to the class of organic compounds known as xanthophylls. These 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.

1.2. Taxonomy Tree

1.3. Alternative Parent

Secondary alcohols; Hydrocarbon derivatives;

1.4. Molecular Framework

Aliphatic homomonocyclic compounds

1.5. Substituents

Xanthophyll; Secondary alcohol; Organic oxygen compound; Hydrocarbon derivative; Organooxygen compound; Alcohol; Aliphatic homomonocyclic compound

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
10.4033 40.46 2 2 42 10 0 0 18.4102 915.397 689.188 0.621464

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-83.957642 1.76 -4.481 -7.97881 -0.98279 3.498

4. Compound Reactivity

DLP nRFG nLMR
6 25 2

5. Topkat Properties

WOE Prediction Ames Prediction DTP Prediction Rat Oral LD50 (g/kg body weight) Rat Inhalational LC50 (mg/m3/h) Chronic LOAEL (g/kg body weight) Skin Irritancy Skin Sensitization Ocular Irritancy Aerobic Biodegradability Prediction Fathead Minnow LC50 (g/l) Daphnia EC50 (mg/l)
Carcinogen Non-Mutagen Toxic 3.70395 384.15 0.000690053 Moderate Weak None Degradable 1.41E-7 0.0141179

6. Drug-Likeliness Test

Lipinski's rule of five Jorgensen's rule of three Goshe filter Veber filter PAINS1 PAINS2 PAINS3
No Yes No Yes Yes Yes Yes

7. Synonyms

Name
Lutein
XANTHOPHYLL
127-40-2
Bo-Xan
Luteine
trans-Lutein
Vegetable lutein
UNII-X72A60C9MT
Lutein ester
(3R,3'R,6'R)-Lutein
Vegetable luteol
all-trans-Lutein
all-trans-(+)-Xanthophyll
Lutein, all-trans-
X72A60C9MT
CHEBI:28838
E 161b
KBPHJBAIARWVSC-RGZFRNHPSA-N
Xanthophyll, all-trans-(+)-
beta,epsilon-Carotene-3,3'-diol
Lutamax
EINECS 204-840-0
NSC 59193
all-trans-Xanthophyll
Xanthophyll (Lutein)
beta,epsilon-Carotene-3,3'-diol, (3R,3'R,6'R)-
.beta.,.epsilon.-Carotene-3,3'-diol, (3R,3'R,6'R)-
Xantofyl
FloraGLO
FloraGLO Lutein
Lutein A
9-cis-Lutein
NCGC00167965-01
(all-E)-Lutein
13-cis-Lutein
15-cis-Lutein
13'-cis-Lutein
Oro Glo 7
(9'Z)-Lutein
AC1NQY9C
Xanthophyll, from marigold
Lutein, analytical standard
DSSTox_CID_26749
DSSTox_RID_81874
DSSTox_GSID_46749
SCHEMBL19342
CHEMBL173929
DTXSID8046749
BCBcMAP01_000190
(3R,3'R,6S)-4,5-DIDEHYDRO-5,6-DIHYDRO-BETA,BETA-CAROTENE-3,3'-DIOL
MolPort-023-220-417
OS 24
180580-60-3
ZINC8221225
Tox21_112594
LMPR01070274
AKOS008901394
DB00137
.beta.,.epsilon.-Carotene-3,3'-diol
SMP1_000317
AK143308
AK322374
CAS-127-40-2
DR003291
N653
E 161
C08601
(3R,3'R,6'R)-|A,|A-Carotene-3,3'-diol
(3R,3'R,6'R)-beta,epsilon-carotene-3,3'-diol
6'-Hydro-4',5'-dehydro-|A-carotene-3,3'-diol
Lutein solution, 1 mg/L in ethanol, analytical standard
4',5'-Didehydro-6'-hydro-.beta.-carotene-3,3'-diol #
AB972DAC-E626-49F1-898D-598AF7729FD0
Lutein, pharmaceutical secondary standard
traceable to USP
(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,4R)-4-hydroxy-2,6,6-trimethyl-cyclohex-2-en-1-yl]-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethyl-cyclohex-3-en-1-ol
(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
(1R,4R)-4-((1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-((R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl)-3,5,5-trimethylcyclohex-2-enol
1407-74-5
148124-35-0
25312-96-3
28368-07-2
29414-89-9
34026-62-5
34445-91-5
()-Lutein
Certified Reference Material

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
Lutein
Commelina benghalensis L Leaf 2
Ipomoea aquatica Whole Plant 4 , 7
Lepidium sativum Seed 2
Olea europea Leaf 3
Sesbania grandiflora Leaf 2

9. Targets

ID Target Name Gene Symbol Organism Protein Crystal Complex Activity Values Reference
Potency (nM) Ki (nM) IC50 (nM) Kd (nM) EC50 (nM) kon (M-1-s-1) koff (s-1) Biological Assay DOI Article PMID PubChem AID
56 androgen receptor AR Homo sapiens 18.9959 743063
56 androgen receptor AR Homo sapiens 26.6032 743042
57 estrogen receptor 1 ESR1 Homo sapiens 26.8325 743069
57 estrogen receptor 1 ESR1 Homo sapiens 60.0704 743075
55 nuclear receptor subfamily 3 group C member 1 NR3C1 Homo sapiens 23.9145 720692
72 peroxisome proliferator activated receptor gamma PPARG Homo sapiens 23.9145 743094
51 retinoic acid receptor alpha RARA Homo sapiens 25.1 1159612
54 retinoid X receptor alpha RXRA Homo sapiens 5.74 1159611
47 thyroid hormone receptor beta Thrb Rattus norvegicus 21.1317 743065
47 thyroid hormone receptor beta Thrb Rattus norvegicus 24.6377 743067
81 tumor protein p53 TP53 Homo sapiens 33.4915 651631
81 tumor protein p53 TP53 Homo sapiens 33.4915 720552
67 tyrosyl-DNA phosphodiesterase 1 TDP1 Homo sapiens 26.6086 686978

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
348677195Chemieliva Pharmaceutical Co., LtdSource URLSource DetailPBCM0195346Source Record URL
251915778AvaChem ScientificSource URLSource Detail127-40-2Source Record URL
251917126AvaChem ScientificSource URLSource Detail2320Source Record URL
315446582Phion LtdSource URLSource Detail35690288Source Record URL
274950767ChemFacesSource URLSource DetailCFN99384Source Record URL
369356235AmbinterSource URLSource DetailAmb17621317Source Record URL
252071745Bide Pharmatech Ltd.Source URLSource DetailBD39535Source Record URL
329748359Sigma-AldrichSource URLSource Detail07168_SIALSource Record URL
329768618Sigma-AldrichSource URLSource Detail79766_SIALSource Record URL
329823562Sigma-AldrichSource URLSource DetailPHR1699_SIALSource Record URL
24902152Sigma-AldrichSource URLSource DetailX6250_SIGMASource Record URL
329978275Acorn PharmaTech Product ListSource URLSource DetailACN-035721Source Record URL
57358075NovoSeekSource URLSource Detail5281243Source Record URL
322063938ChemShuttleSource URLSource Detail146164Source Record URL
354317648iChemical Technology USA IncSource URLSource DetailEBD2197452Source Record URL
3632409801717 CheMall CorporationSource URLSource DetailBG08053621Source Record URL
145212657AKos Consulting & SolutionsSource URLSource DetailAKOS008901394Source Record URL
316964826ParchemSource URLSource Detail22893Source Record URL
346551802LabNetwork, a WuXi AppTec CompanySource URLSource DetailLN01318215Source Record URL
318504983CambridgeChemSource URLSource DetailCB21485Source Record URL
113854859ABI ChemSource URLSource DetailAC1NQY9CSource Record URL
162222449Chembase.cnSource URLSource Detail128135Source Record URL
29204348R&D ChemicalsSource URLSource Detail0306Source Record URL
310118587Aurora Fine Chemicals LLCSource URLSource DetailA17.890.870Source Record URL
313074801ClearsynthSource URLSource DetailCS-O-01794Source Record URL
162181889AK Scientific, Inc. (AKSCI)Source URLSource DetailN653Source Record URL
319452583eNovation ChemicalsSource URLSource DetailD382545Source Record URL
258473464ZINCSource URLSource DetailZINC8221225Source Record URL
189562500MolPortSource URLSource DetailMolPort-023-220-417Source Record URL