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[ CAS No. 10236-47-2 ] {[proInfo.proName]}

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Chemical Structure| 10236-47-2
Chemical Structure| 10236-47-2
Structure of 10236-47-2 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations

Tonduru, Arun Kumar ; Maljaei, Seyed Hamed ; Adla, Santosh Kumar , et al. DOI: PubMed ID:

Abstract: OATP1C1 (organic anion-transporting polypeptide 1C1) transports thyroid hormones, particularly thyroxine (T4), into human astrocytes. In this study, we investigated the potential of utilizing OATP1C1 to improve the delivery of anti-inflammatory drugs into glial cells. We designed and synthesized eight novel prodrugs by incorporating T4 and 3,5-diiodo-L-tyrosine (DIT) as promoieties to selected anti-inflammatory drugs. The prodrug uptake in OATP1C1-expressing human U-87MG glioma cells demonstrated higher accumulation with T4 promoiety compared to those with DIT promoiety or the parent drugs themselves. In silico models of OATP1C1 suggested dynamic binding for the prodrugs, wherein the pose changed from vertical to horizontal. The predicted binding energies correlated with the transport profiles, with T4 derivatives exhibiting higher binding energies when compared to prodrugs with a DIT promoiety. Interestingly, the prodrugs also showed utilization of oatp1a4/1a5/1a6 in mouse primary astrocytes, which was further supported by docking studies and a great potential for improved brain drug delivery.

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Product Details of [ 10236-47-2 ]

CAS No. :10236-47-2 MDL No. :MFCD00148888
Formula : C27H32O14 Boiling Point : -
Linear Structure Formula :HOC6H4C9H5O(O)(OH)OC5H5O(CH2OH)(OH)2OC5H5O(CH3)(OH)3 InChI Key :DFPMSGMNTNDNHN-ZPHOTFPESA-N
M.W : 580.53 Pubchem ID :442428
Synonyms :
Naringoside;NSC 5548;AI3-19008;Aurantiin
Chemical Name :(S)-7-(((2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one

Calculated chemistry of [ 10236-47-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 41
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.52
Num. rotatable bonds : 6
Num. H-bond acceptors : 14.0
Num. H-bond donors : 8.0
Molar Refractivity : 134.91
TPSA : 225.06 ?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) : -10.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.96
Log Po/w (XLOGP3) : -0.44
Log Po/w (WLOGP) : -1.49
Log Po/w (MLOGP) : -2.77
Log Po/w (SILICOS-IT) : -1.64
Consensus Log Po/w : -0.87

Druglikeness

Lipinski : 3.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 3.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -2.98
Solubility : 0.604 mg/ml ; 0.00104 mol/l
Class : Soluble
Log S (Ali) : -3.82
Solubility : 0.0877 mg/ml ; 0.000151 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.49
Solubility : 187.0 mg/ml ; 0.321 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 6.16

Safety of [ 10236-47-2 ]

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

Application In Synthesis of [ 10236-47-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 10236-47-2 ]

[ 10236-47-2 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 10236-47-2 ]
  • [ 578-74-5 ]
Reference： [1] Carbohydrate Research, 2012, vol. 357, p. 41 - 46
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