Showing Compound Lutein (FDB015471)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:52 UTC

Update date

2019-11-26 03:11:38 UTC

Primary ID

FDB015471

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Lutein

Description

Lutein, also known as xanthophyll or bo-xan, 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. Thus, lutein is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on Lutein.

CAS Number

127-40-2

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-BETA,BETA-carotene-3,3'-diol	ChEBI
Bo-xan	ChEBI
e 161b	ChEBI
Xanthophyll	ChEBI
(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-b,b-carotene-3,3'-diol	Generator
(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-β,β-carotene-3,3'-diol	Generator
Lutein F	MeSH
Lutein g	MeSH
Lutein, gamma	MeSH
gamma Lutein	MeSH
(3R,3'R,6'R)-Lutein	HMDB
(3R,3'R,6'R)-beta,epsilon-Carotene-3,3'-diol	HMDB
(3R,3'R,6'R)-β,ε-Carotene-3,3'-diol	HMDB
(3R,3’R,6’R)-Lutein	HMDB
(3R,3’R,6’R)-β,ε-Carotene-3,3’-diol	HMDB
(all-E)-Lutein	HMDB
6'-Hydro-4',5'-dehydro-beta-carotene-3,3'-diol	HMDB
6'-Hydro-4',5'-dehydro-β-carotene-3,3'-diol	HMDB
6’-Hydro-4’,5’-dehydro-β-carotene-3,3’-diol	HMDB
Lutein	HMDB
Luteine	HMDB
all-trans-(+)-Xanthophyll	HMDB
all-trans-Lutein	HMDB
all-trans-Xanthophyll	HMDB
trans-Lutein	HMDB
3,3'-Dihydroxy-alpha-carotene	biospider
All-trans-(+)-xanthophyll	biospider
All-trans-lutein	biospider
b,e-Carotene-3,3'-diol	db_source
beta,epsilon-Carotene-3,3'-diol	biospider
beta,epsilon-Carotene-3,3'-diol, (3R,3'R,6'R)-	biospider
Lutein ester	HMDB
Lutein, all-trans-	biospider
Trans-lutein	biospider
Vegetable lutein	HMDB
Vegetable luteol	HMDB
Xanthophyll, all-trans-(+)-	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.00073 g/L	ALOGPS
logP	8.29	ALOGPS
logP	8.55	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	18.22	ChemAxon
pKa (Strongest Basic)	-0.91	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	195.06 m³·mol⁻¹	ChemAxon
Polarizability	74.26 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C40H56O2

IUPAC name

(1R,4R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-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-en-1-ol

InChI Identifier

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

Isomeric SMILES

C\C(\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C

Average Molecular Weight

568.886

Monoisotopic Molecular Weight

568.428031043

Classification

Description

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Tetraterpenoids

Direct Parent

Xanthophylls

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

carotenol (CHEBI:28838 )
C40 isoprenoids (tetraterpenes) (C08601 )
Carotenoids (C08601 )
C40 isoprenoids (tetraterpenes) (LMPR01070274 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 84.45%; H 9.92%; O 5.62%	DFC
Melting Point	Mp 196°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]18643.9 +160 (CHCl3)	DFC
Spectroscopic UV Data	472 () (MeOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Lutein, "Lutein,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lutein, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lutein, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lutein, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lutein, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lutein, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lutein, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-0942120000-1ea7d21108843411033c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0170-0942220000-6f1a6499f3edad61c0e8	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0170-0942220000-35ebb4c0d96329a15eb9	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00n0-0942120000-6f0f9e5c558e5fc6fc39	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gb9-0111190000-56a7b3ad9850d88a093a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0frt-0729640000-fa9f79f8a73fa60b8abf	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-2439510000-8c70ee5c9af7440a4672	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000090000-e64043a148b331ba05a6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0000090000-a48901fc52e8e64be250	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udr-0522590000-ed879e2e3d350ac0e502	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0121930000-b93c4284d63c87f0039c	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uel-0113920000-f619218ed5b32e075e70	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0wmi-0059500000-ba48ee62bc6ea7e22dbf	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0202090000-e7ff503087b047287234	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0405490000-4908259aa27c690d5b58	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0201-0519300000-3ec7b022b5aedb2ab3d0	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4938343

ChEMBL ID

Not Available

KEGG Compound ID

C08601

Pubchem Compound ID

6433159

Pubchem Substance ID

Not Available

ChEBI ID

28838

Phenol-Explorer ID

Not Available

DrugBank ID

DB00137

HMDB ID

HMDB03233

CRC / DFC (Dictionary of Food Compounds) ID

KCN64-A:KCN64-A

EAFUS ID

3880

Dr. Duke ID

XANTHOPHYLL|LUTEIN

BIGG ID

Not Available

KNApSAcK ID

C00003776

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Lutein

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Anti-atherosclerotic	38070	An agent that prevents or slows the formation of atherosclerosis, a condition characterized by plaque buildup in arteries. It reduces inflammation, improves lipid profiles, and inhibits platelet aggregation, commonly used to manage cardiovascular diseases, such as coronary artery disease, and prevent heart attacks and strokes.	DUKE
Anti-cancer	35610	An agent that inhibits the growth and proliferation of cancer cells, used to treat and manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, to reduce tumor size, prevent metastasis, and improve patient survival.	DUKE
Anti-maculitic		An agent that reduces macular inflammation, commonly used in managing age-related macular degeneration and diabetic macular edema, promoting vision preservation and reducing disease progression.	DUKE
Anti nyctalopic		An agent that enhances sight in dim light or at night, countering nyctalopia (night blindness). Its biological role is to improve visual acuity in low-light conditions. Therapeutically, it has applications in treating night blindness and other visual impairments. Key medical uses include managing vitamin A deficiency, a common cause of night blindness, and improving visual function in individuals with impaired low-light vision.	DUKE
Anti-oxidant	22586	An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.	DUKE
Anti proliferant		An agent that prevents or inhibits cell growth and division, used therapeutically to treat cancer, manage tumor growth, and prevent restenosis after angioplasty, reducing abnormal cell proliferation.	DUKE
Anti radicular		An agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management.	DUKE
Anti-retinitic		An agent that relieves inflammation of the retina (retinitis), reducing symptoms and promoting healing. It has therapeutic applications in ophthalmology, with key medical uses including treating retinal infections, injuries, and diseases such as retinitis pigmentosa.	DUKE
Antitumor	35610	An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.	DUKE
Bruchifuge	25944	An anthelmintic agent that expels or kills intestinal parasites, particularly tapeworms. Its therapeutic applications include treating parasitic infections, with key medical uses in managing tapeworm infestations and promoting gastrointestinal health.	DUKE
Colorant	37958	A substance that imparts color, with no inherent biological role. Therapeutically, colorants are used to enhance visual appeal and identification of medications. Medically, they are used in diagnostic imaging, such as contrast agents, and in ophthalmic applications to aid in vision correction and protection.	DUKE
Insectifuge	24852	A substance that repels insects, playing a biological role in plant defense. Therapeutically, it has applications in preventing insect-borne diseases. Key medical uses include topical repellents for malaria, dengue fever, and other vector-borne illnesses, reducing the risk of transmission.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Prooxidant		An agent that induces oxidative stress by generating reactive oxygen species (ROS) or inhibiting antioxidant systems, playing a role in cell damage and disease progression. Therapeutically, prooxidants have applications in cancer treatment, as they can selectively kill cancer cells. Key medical uses include cancer therapy and antimicrobial treatments.	DUKE
Quinone-reductase inducer		An agent that stimulates quinone reductase enzymatic activity, enhancing cellular antioxidant defenses and protecting against carcinogens, with therapeutic applications in cancer chemoprevention and potential uses in managing oxidative stress-related diseases.	DUKE
Retinoprotectant		An agent that protects the retina from damage, alleviating or preventing conditions such as retinal degeneration and age-related macular degeneration, with therapeutic applications in ophthalmology to preserve vision and prevent blindness.	DUKE
Ubiquiot		An antioxidant that protects cells from damage, playing a crucial role in energy production. Therapeutically, it has applications in managing neurodegenerative and cardiovascular diseases, with key medical uses including reducing oxidative stress and improving mitochondrial function.	DUKE