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[ CAS No. 144-68-3 ] {[proInfo.proName]}

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Chemical Structure| 144-68-3
Chemical Structure| 144-68-3
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Product Citations

Product Citations

Chazan, Ariel ; Das, Ishita ; Fujiwara, Takayoshi , et al. DOI: PubMed ID:

Abstract: Energy transfer from light-harvesting ketocarotenoids to the light-driven proton pump xanthorhodopsins has been previously demonstrated in two unique cases: an extreme halophilic bacterium and a terrestrial cyanobacterium. Attempts to find carotenoids that bind and transfer energy to abundant rhodopsin proton pumps from marine photoheterotrophs have thus far failed. Here we detected light energy transfer from the widespread hydroxylated carotenoids zeaxanthin and lutein to the retinal moiety of xanthorhodopsins and proteorhodopsins using functional metagenomics combined with chromophore extraction from the environment. The light-harvesting carotenoids transfer up to 42% of the harvested energy in the violet- or blue-light range to the green-light absorbing retinal chromophore. Our data suggest that these antennas may have a substantial effect on rhodopsin phototrophy in the world's lakes, seas and oceans. However, the functional implications of our findings are yet to be discovered.

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Product Details of [ 144-68-3 ]

CAS No. :144-68-3 MDL No. :MFCD08435940
Formula : C40H56O2 Boiling Point : -
Linear Structure Formula :- InChI Key :JKQXZKUSFCKOGQ-QAYBQHTQSA-N
M.W : 568.87 Pubchem ID :5280899
Synonyms :
Anchovyxanthin;Zeaxanthol;beta-Carotene-3,3'-diol;Xanthophyll 3
Chemical Name :(1R,1'R)-4,4'-((1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl)bis(3,5,5-trimethylcyclohex-3-enol)

Calculated chemistry of [ 144-68-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 42
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.45
Num. rotatable bonds : 10
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 186.76
TPSA : 40.46 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -2.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 7.27
Log Po/w (XLOGP3) : 10.91
Log Po/w (WLOGP) : 10.55
Log Po/w (MLOGP) : 6.96
Log Po/w (SILICOS-IT) : 10.9
Consensus Log Po/w : 9.32

Druglikeness

Lipinski : 2.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 1.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -9.58
Solubility : 0.00000015 mg/ml ; 0.0000000003 mol/l
Class : Poorly soluble
Log S (Ali) : -11.72
Solubility : 0.0000000011 mg/ml ; 0.0 mol/l
Class : Insoluble
Log S (SILICOS-IT) : -5.94
Solubility : 0.000652 mg/ml ; 0.00000115 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 6.78

Safety of [ 144-68-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:
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