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[ CAS No. 500-38-9 ] {[proInfo.proName]}

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Chemical Structure| 500-38-9
Chemical Structure| 500-38-9
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Product Citations

Product Citations

Wegner, Scott A ; Kim, Hahn ; Avalos, José L DOI: PubMed ID:

Abstract: Lactate transport plays a crucial role in the metabolism, microenvironment, and survival of cancer cells. However, current drugs targeting either MCT1 or MCT4, which traditionally mediate lactate import or efflux respectively, show limited efficacy beyond in vitro models. This limitation partly arises from the existence of both isoforms in certain tumors, however existing high-affinity MCT1/4 inhibitors are years away from human testing. Therefore, we conducted an optogenetic drug screen in Saccharomyces cerevisiae on a subset of the FDA-approved drug library to identify existing scaffolds that could be repurposed as monocarboxylate transporter (MCT) inhibitors. Our findings show that several existing drug classes inhibit MCT1 activity, including non-steroidal estrogens, non-steroidal anti-inflammatory drugs (NSAIDs), and natural products (in total representing approximately 1% of the total library, 78 out of 6400), with a moderate affinity (IC50 1.8–21 μM). Given the well-tolerated nature of NSAIDs, and their known anticancer properties associated with COX inhibition, we chose to further investigate their MCT1 inhibition profile. The majority of NSAIDs in our screen cluster into a single large structural grouping. Moreover, this group is predominantly comprised of FDA-approved NSAIDs, with seven exhibiting moderate MCT1 inhibition. Since these molecules form a distinct structural cluster with known NSAID MCT4 inhibitors, such as diclofenac, ketoprofen, and indomethacin, we hypothesize that these newly identified inhibitors may also inhibit both transporters. Consequently, NSAIDs as a class, and piroxicam specifically (IC50 4.4 μM), demonstrate MCT1 inhibition at theoretically relevant human dosages, suggesting immediate potential for standalone MCT inhibition or combined anticancer therapy.

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Product Details of [ 500-38-9 ]

CAS No. :500-38-9 MDL No. :MFCD00002206
Formula : C18H22O4 Boiling Point : -
Linear Structure Formula :- InChI Key :HCZKYJDFEPMADG-UHFFFAOYSA-N
M.W : 302.36 Pubchem ID :4534
Synonyms :
NDGA;NSC 4291
Chemical Name :4,4'-(2,3-Dimethylbutane-1,4-diyl)bis(benzene-1,2-diol)

Calculated chemistry of [ 500-38-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.33
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 4.0
Molar Refractivity : 88.02
TPSA : 80.92 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.08 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.38
Log Po/w (XLOGP3) : 4.31
Log Po/w (WLOGP) : 3.57
Log Po/w (MLOGP) : 2.74
Log Po/w (SILICOS-IT) : 3.45
Consensus Log Po/w : 3.29

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.5
Solubility : 0.00948 mg/ml ; 0.0000314 mol/l
Class : Moderately soluble
Log S (Ali) : -5.72
Solubility : 0.000572 mg/ml ; 0.00000189 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.28
Solubility : 0.0157 mg/ml ; 0.000052 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.68

Safety of [ 500-38-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P301+P312+P330 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:
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