Lutein

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	308e0063-51bb-4dd2-990b-6858c420a4cb
Taxonomy	Lipids and lipid-like molecules > Prenol lipids > Tetraterpenoids > Carotenoids > Xanthophylls
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
SMILES (Canonical)	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
SMILES (Isomeric)	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
Popularity	15,218 references in papers

Physical and Chemical Properties

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Molecular Formula	C₄₀H₅₆O₂
Molecular Weight	568.90 g/mol
Exact Mass	568.42803102 g/mol
Topological Polar Surface Area (TPSA)	40.50 Å²
XlogP	11.00
Atomic LogP (AlogP)	10.40
H-Bond Acceptor	2
H-Bond Donor	2
Rotatable Bonds	10

Synonyms

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XANTHOPHYLL

127-40-2

Bo-Xan

Vegetable lutein

Vegetable luteol

all-trans-Lutein

trans-Lutein

Xantofyl

Lutein ester

all-trans-(+)-Xanthophyll

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9956	99.56%
Caco-2	-	0.7944	79.44%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6198	61.98%
OATP2B1 inhibitior	-	0.7150	71.50%
OATP1B1 inhibitior	+	0.7737	77.37%
OATP1B3 inhibitior	+	0.9556	95.56%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9947	99.47%
P-glycoprotein inhibitior	+	0.7859	78.59%
P-glycoprotein substrate	-	0.5509	55.09%
CYP3A4 substrate	+	0.6532	65.32%
CYP2C9 substrate	-	0.8191	81.91%
CYP2D6 substrate	-	0.7760	77.60%
CYP3A4 inhibition	-	0.8808	88.08%
CYP2C9 inhibition	-	0.7723	77.23%
CYP2C19 inhibition	+	0.5225	52.25%
CYP2D6 inhibition	-	0.9368	93.68%
CYP1A2 inhibition	-	0.9079	90.79%
CYP2C8 inhibition	+	0.5242	52.42%
CYP inhibitory promiscuity	-	0.6267	62.67%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7348	73.48%
Carcinogenicity (trinary)	Non-required	0.5753	57.53%
Eye corrosion	-	0.9776	97.76%
Eye irritation	-	0.9140	91.40%
Skin irritation	-	0.6972	69.72%
Skin corrosion	-	0.9646	96.46%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8887	88.87%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.8229	82.29%
skin sensitisation	+	0.8612	86.12%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	+	0.6966	69.66%
Acute Oral Toxicity (c)	III	0.7696	76.96%
Estrogen receptor binding	+	0.8326	83.26%
Androgen receptor binding	+	0.6904	69.04%
Thyroid receptor binding	+	0.7189	71.89%
Glucocorticoid receptor binding	+	0.8970	89.70%
Aromatase binding	-	0.4936	49.36%
PPAR gamma	+	0.7543	75.43%
Honey bee toxicity	-	0.7885	78.85%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9234	92.34%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.50%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.94%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	92.94%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.80%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.58%	86.33%
CHEMBL1937	Q92769	Histone deacetylase 2	85.95%	94.75%
CHEMBL1870	P28702	Retinoid X receptor beta	85.51%	95.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.27%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.86%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.20%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.04%	92.94%
CHEMBL2004	P48443	Retinoid X receptor gamma	82.52%	100.00%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	82.37%	85.30%
CHEMBL2061	P19793	Retinoid X receptor alpha	81.35%	91.67%
CHEMBL2581	P07339	Cathepsin D	81.33%	98.95%
CHEMBL3492	P49721	Proteasome Macropain subunit	81.10%	90.24%
CHEMBL3524	P56524	Histone deacetylase 4	80.63%	92.97%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.54%	91.71%
CHEMBL4208	P20618	Proteasome component C5	80.12%	90.00%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Acacia adunca

Adiantum philippense

Aesculus hippocastanum

Agastache foeniculum

Ageratum corymbosum

Aldama incana

Amentotaxus yunnanensis

Artemisia pedemontana subsp. assoana