Lutein 5,6-epoxide

Details

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Internal ID e1651b63-5952-4d0c-aa26-7833efd6ea81
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Tetraterpenoids > Carotenoids > Xanthophylls
IUPAC Name (1R,3S,6S)-6-[(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]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
SMILES (Canonical) CC1=CC(CC(C1C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC23C(CC(CC2(O3)C)O)(C)C)C)C)(C)C)O
SMILES (Isomeric) CC1=C[C@@H](CC([C@H]1/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/[C@]23[C@](O2)(C[C@H](CC3(C)C)O)C)/C)/C)(C)C)O
InChI InChI=1S/C40H56O3/c1-29(17-13-19-31(3)21-22-36-33(5)25-34(41)26-37(36,6)7)15-11-12-16-30(2)18-14-20-32(4)23-24-40-38(8,9)27-35(42)28-39(40,10)43-40/h11-25,34-36,41-42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,22-21+,24-23+,29-15+,30-16+,31-19+,32-20+/t34-,35-,36-,39+,40-/m0/s1
InChI Key DYUUPIKEWLHQGQ-FJOIUHRLSA-N
Popularity 4 references in papers

Physical and Chemical Properties

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Molecular Formula C40H56O3
Molecular Weight 584.90 g/mol
Exact Mass 584.42294564 g/mol
Topological Polar Surface Area (TPSA) 53.00 Ų
XlogP 10.40
Atomic LogP (AlogP) 9.61
H-Bond Acceptor 3
H-Bond Donor 2
Rotatable Bonds 10

Synonyms

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Taraxanthin
28368-08-3
Epoxylutein
Eloxanthin
Isolutein
5,6-Epoxylutein
Xanthophyll epoxide
anti-Lutein epoxide
5,6-Monoepoxylutein
All-trans-lutein epoxide
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Lutein 5,6-epoxide

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9879 98.79%
Caco-2 - 0.8018 80.18%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability + 0.5143 51.43%
Subcellular localzation Mitochondria 0.4491 44.91%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8266 82.66%
OATP1B3 inhibitior + 0.9710 97.10%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior + 0.9831 98.31%
P-glycoprotein inhibitior + 0.7528 75.28%
P-glycoprotein substrate - 0.6009 60.09%
CYP3A4 substrate + 0.6637 66.37%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.7719 77.19%
CYP3A4 inhibition - 0.9038 90.38%
CYP2C9 inhibition - 0.7637 76.37%
CYP2C19 inhibition - 0.5600 56.00%
CYP2D6 inhibition - 0.9415 94.15%
CYP1A2 inhibition - 0.8123 81.23%
CYP2C8 inhibition + 0.4443 44.43%
CYP inhibitory promiscuity - 0.7699 76.99%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.8720 87.20%
Carcinogenicity (trinary) Non-required 0.5202 52.02%
Eye corrosion - 0.9836 98.36%
Eye irritation - 0.9117 91.17%
Skin irritation - 0.6565 65.65%
Skin corrosion - 0.9366 93.66%
Ames mutagenesis - 0.5600 56.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8327 83.27%
Micronuclear - 0.6800 68.00%
Hepatotoxicity - 0.7032 70.32%
skin sensitisation + 0.5194 51.94%
Respiratory toxicity + 0.5889 58.89%
Reproductive toxicity + 0.6000 60.00%
Mitochondrial toxicity + 0.5750 57.50%
Nephrotoxicity + 0.4761 47.61%
Acute Oral Toxicity (c) III 0.4264 42.64%
Estrogen receptor binding + 0.8358 83.58%
Androgen receptor binding + 0.7219 72.19%
Thyroid receptor binding + 0.6806 68.06%
Glucocorticoid receptor binding + 0.8421 84.21%
Aromatase binding + 0.5783 57.83%
PPAR gamma + 0.7381 73.81%
Honey bee toxicity - 0.7892 78.92%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.5600 56.00%
Fish aquatic toxicity + 0.8978 89.78%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.24% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.22% 96.09%
CHEMBL4040 P28482 MAP kinase ERK2 93.32% 83.82%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.70% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.37% 95.56%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.15% 100.00%
CHEMBL241 Q14432 Phosphodiesterase 3A 83.20% 92.94%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.81% 95.89%
CHEMBL1870 P28702 Retinoid X receptor beta 80.92% 95.00%

Cross-Links

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PubChem 5281244
NPASS NPC96403
LOTUS LTS0218271
wikiData Q27103135