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[ CAS No. 327-97-9 ] {[proInfo.proName]}

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Chemical Structure| 327-97-9
Chemical Structure| 327-97-9
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Product Citations

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Minwoo Bae ; Chi Le (Chip) ; Raaj S. Mehta , et al. DOI: PubMed ID:

Abstract: Gut microbial catechol dehydroxylases are a largely uncharacterized family of metalloenzymes that potentially impact human health by metabolizing dietary polyphenols. Here, we use metatranscriptomics (MTX) to identify highly transcribed catechol-dehydroxylase-encoding genes in human gut microbiomes. We discover a prevalent, previously uncharacterized catechol dehydroxylase (Gp Hcdh) from Gordonibacter pamelaeae that dehydroxylates hydrocaffeic acid (HCA), an anti-inflammatory gut microbial metabolite derived from plant-based foods. Further analyses suggest that the activity of Gp Hcdh may reduce anti-inflammatory benefits of polyphenol-rich foods. Together, these results show the utility of combining MTX analysis and biochemical characterization for gut microbial enzyme discovery and reveal a potential link between host inflammation and a specific polyphenol-metabolizing gut microbial enzyme.

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Scott, Jared Lee ; DOI:

Abstract: Breast cancer (BC) is the second greatest contributor to the death of women, second only to heart disease, and is the most common type of cancer. BC treatments involve the administration of adjuvant chemotherapies which often have side effects that prevent patients from completing the full course of drugs or the refusal to take these potentially lifesaving treatments. Many chemotherapy drugs are developed from plants, and some plant extracts can exhibit significant anticancer activities while also having less toxic side effects. However, these potential "plant therapeutics" suffer from poor oral bioavailability. The Apiaceae plant family consists of several species that are used as culinarily spices including anise, celery, cumin, and coriander, all of which have demonstrated antioxidant, chemopreventive, and anticancer activities. One method to improve the systemic distribution of anticancer phytochemicals is their encapsulation in naturally produced membrane bound nanoparticles known as exosomes. Exosomes are produced by most eukaryotic organisms, as well as some prokaryotes, and are involved in cell-to-cell communication through the delivery of proteins, nucleic acids, and small molecules from one cell to another. Exosomes are found in many extracellular fluids including blood, urine, and milk. Bovine milk exosomes represent a scalable source of exosomes that are already present in the human diet and have been explored as a drug delivery system that can increase effectiveness and improve bioavailability. To enhance the loading potential and anticancer bioactivity of Apiaceae phytochemicals, an acid hydrolysis (AH) of the glycoside compounds present in ethanolic spice extracts was performed on eight ethanolic spice extracts. The antiproliferative effects of AH extracts and exosomal formulations were assayed with three model types of BC cells. Cumin was characterized in greater detail as these extracts had the highest concentration of terpenoids and alkaloids while also having significant concentrations of phenolics and responded well to AH with increased antiproliferative activity and exosomal loading. Extracts and exosomal formulations exhibited broad antiproliferative effects with lower IC50s in the extracts delivered with exosomes. The phytochemical contents of AH-cumin extracts and exosomal formulations were assayed with HPLC-DAD, LC-MS/MS, and GC-MS, while the potential anticancer mechanisms of these treatments were investigated in triple negative BC (TNBC). AHcumin extracts were determined to have numerous phenolic compounds, many of which have known anticancer mechanisms, in addition to several alkaloids and lipid compounds, some of which have activities that could contribute to the anticancer effects observed. Mechanistically, AH-cumin extracts and exosomal formulations were shown to interact with multidrug resistance proteins and inhibit lipid metabolism in TNBC cells. These results indicate that acid hydrolyzed cumin extracts delivered through exosome nanoparticles represent a possible avenue towards the development of novel treatments for TNBC, the hardest type of BC to treat.

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Product Details of [ 327-97-9 ]

CAS No. :327-97-9 MDL No. :MFCD00003862
Formula : C16H18O9 Boiling Point : -
Linear Structure Formula :- InChI Key :CWVRJTMFETXNAD-JUHZACGLSA-N
M.W : 354.31 Pubchem ID :1794427
Synonyms :
3-O-Caffeoylquinic acid;Heriguard;3transCaffeoylquinic acid;Chlorogenate;3CQA;3Caffeoylquinic acid;3Caffeoylquinate;3(34Dihydroxycinnamoyl)quinic acid;3(34Dihydroxycinnamoyl)quinate;NSC-407296
Chemical Name :(1S,3R,4R,5R)-3-(((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexanecarboxylic acid

Calculated chemistry of [ 327-97-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 25
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.38
Num. rotatable bonds : 5
Num. H-bond acceptors : 9.0
Num. H-bond donors : 6.0
Molar Refractivity : 83.5
TPSA : 164.75 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.87
Log Po/w (XLOGP3) : -0.42
Log Po/w (WLOGP) : -0.75
Log Po/w (MLOGP) : -1.05
Log Po/w (SILICOS-IT) : -0.61
Consensus Log Po/w : -0.39

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.11

Water Solubility

Log S (ESOL) : -1.62
Solubility : 8.5 mg/ml ; 0.024 mol/l
Class : Very soluble
Log S (Ali) : -2.58
Solubility : 0.942 mg/ml ; 0.00266 mol/l
Class : Soluble
Log S (SILICOS-IT) : 0.4
Solubility : 894.0 mg/ml ; 2.52 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.16

Safety of [ 327-97-9 ]

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 [ 327-97-9 ]

* 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 [ 327-97-9 ]

[ 327-97-9 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 342811-68-1 ]
  • [ 327-97-9 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 26, p. 10605 - 10614
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