NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
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IUPAC Traditional name
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chamomile
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5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
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Synonyms
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5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
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4',5,7-Trihydroxyflavone
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N-[4-(1-Cyanocyclopentyl)phenyl]-2-[[(1-oxido-4-pyridinyl)methyl]amino]-3-pyridinecarboxamide
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Apatinib 25-N-Oxide Hydrochloride
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Apigenine
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Chamomile
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Apigenol
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Spigenin
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Versulin
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C.I. Natural Yellow 1
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4′,5,7-Trihydroxyflavone
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Apigenin
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Apigenin
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Apigenin
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4',5,7-Trihydroxyflavone
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Pelargidenone
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4',5,7-三羟基黄酮
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CAS Number
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EC Number
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MDL Number
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Beilstein Number
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Merck Index
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PubChem SID
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PubChem CID
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CHEBI ID
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CHEMBL
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Chemspider ID
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DrugBank ID
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KEGG ID
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Wikipedia Title
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
ALOGPS 2.1
Acid pKa
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6.574692
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H Acceptors
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5
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H Donor
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3
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LogD (pH = 5.5)
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2.671756
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LogD (pH = 7.4)
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1.7656507
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Log P
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2.7066891
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Molar Refractivity
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72.9139 cm3
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Polarizability
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27.10717 Å3
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Polar Surface Area
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86.99 Å2
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Rotatable Bonds
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1
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Lipinski's Rule of Five
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true
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Log P
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3.07
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LOG S
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-3.36
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Solubility (Water)
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1.18e-01 g/l
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PROPERTIES
PROPERTIES
Physical Property
Safety Information
Pharmacology Properties
Product Information
Bioassay(PubChem)
Solubility
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1 M KOH: soluble50 mg/mL
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Show
data source
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DMSO: soluble27 mg/mL
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Show
data source
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H2O: insoluble
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Show
data source
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Apperance
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Yellow crystalline solid
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Show
data source
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yellow powder
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Show
data source
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Yellow powder
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Show
data source
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yellow to green
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Show
data source
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Melting Point
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>300 °C(lit.)
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Show
data source
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300°C
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Show
data source
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345–350 °C
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Show
data source
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ca 315°C dec.
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Show
data source
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Density
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0.905 g/ml
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Show
data source
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Storage Condition
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-20°C
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Show
data source
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Storage Warning
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Irritant
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Show
data source
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RTECS
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LK9276000
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Show
data source
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European Hazard Symbols
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Irritant (Xi)
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Show
data source
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MSDS Link
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German water hazard class
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3
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Show
data source
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Risk Statements
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36/37/38
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Show
data source
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Safety Statements
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26-36
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Show
data source
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26-37
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Show
data source
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TSCA Listed
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否
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Show
data source
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GHS Pictograms
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Show
data source
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GHS Signal Word
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Warning
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Show
data source
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GHS Hazard statements
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H315-H319-H335
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Show
data source
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GHS Precautionary statements
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P261-P305 + P351 + P338
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Show
data source
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P261-P305+P351+P338-P302+P352-P321-P405-P501A
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Show
data source
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Personal Protective Equipment
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dust mask type N95 (US), Eyeshields, Gloves
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Show
data source
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Storage Temperature
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-20°C
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Show
data source
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2-8°C
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Show
data source
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Gene Information
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human ... ADORA3(140), CDC2(983), CDK5(1020), CDK6(1021), CYP1A2(1544), ESR1(2099), ESR2(2100), GSK3A(2931)mouse ... Hexa(15211)rat ... Adora1(29290), Adora2a(25369), Il4(287287), Tnf(24835)
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Show
data source
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Mechanism of Action
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Tyrosine kinase inhibitor
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Show
data source
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Purity
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≥75% (HPLC)
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Show
data source
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≥95.0% (HPLC)
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Show
data source
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≥97% (TLC)
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Show
data source
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≥99% (HPLC)
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Show
data source
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95%
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Show
data source
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97%
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Show
data source
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99.0
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Show
data source
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Grade
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analytical standard
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Show
data source
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Salt Data
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Free Base
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Show
data source
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Certificate of Analysis
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Impurities
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~2% water
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Show
data source
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<5% acetic acid
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Show
data source
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≤2% water
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Show
data source
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Biological Source
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Found free or as glycosides in the stems, roots, leaves, seeds or fruit of a very wide range of plant spp.
Found also in some fossil leaf tissues
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Show
data source
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from parsley
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Show
data source
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Shelf Life
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(limited shelf life, expiry date on the label)
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Show
data source
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Application(s)
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Antispasmolytic agent
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Show
data source
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Shows antineoplastic activity in vitro
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Show
data source
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Empirical Formula (Hill Notation)
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C15H10O5
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Show
data source
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DETAILS
DETAILS
DrugBank
Apollo Scientific
Selleck Chemicals
Wikipedia
Sigma Aldrich
TRC
Selleck Chemicals -
S2262
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Research Area: Cancer Biological Activity: Apigenin is a potent CYP2C9 inhibitor with an IC50 of 23 pM. CYP2C9 is an enzyme responsible for the metabolism of many pharmaceutical compounds in the body. Apigenin is commonly recognised as to mediate at least part of the chemopreventive action of vegetables and fruits in the cancerous process. Recently it was shown that apigenin induces a process called autophagia (a kind of cellular dormancy) which may well explain it chemopreventive properties but at the same time induces resistance against chemotherapy. Apigenin is a flavone that is the aglycone of several glycosides. [1][2]References on Apigenin[1] http://en.wikipedia.org/wiki/Apigenin, , [2] Drug Metab Dispos., 2009 Mar, 37(3):629-34 |
Sigma Aldrich -
460745
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Biochem/physiol Actions A plant flavonoid that has been found to inhibit cell proliferation by arresting the cell cycle at the G2/M phase. Inhibition of growth through cell cycle arrest and induction of apoptosis appear to be related to induction of p53.Inhibits PMA-mediated tumor promotion by inhibiting protein kinase C1 and the resulting suppression of oncogene expression. It has also been reported to inhibit topoisomerase I-catalyzed DNA re-ligation and enhance gap junctional intercellular communication. |
Sigma Aldrich -
A281
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Biochem/physiol Actions A plant flavonoid that has been found to inhibit cell proliferation by arresting the cell cycle at the G2/M phase. Inhibition of growth through cell cycle arrest and induction of apoptosis appear to be related to induction of p53.Inhibits PMA-mediated tumor promotion by inhibiting protein kinase C1 and the resulting suppression of oncogene expression. It has also been reported to inhibit topoisomerase I-catalyzed DNA re-ligation and enhance gap junctional intercellular communication. |
Sigma Aldrich -
42251
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Biochem/physiol Actions A plant flavonoid that has been found to inhibit cell proliferation by arresting the cell cycle at the G2/M phase. Inhibition of growth through cell cycle arrest and induction of apoptosis appear to be related to induction of p53.Inhibits PMA-mediated tumor promotion by inhibiting protein kinase C1 and the resulting suppression of oncogene expression. It has also been reported to inhibit topoisomerase I-catalyzed DNA re-ligation and enhance gap junctional intercellular communication. |
Sigma Aldrich -
10793
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Biochem/physiol Actions A plant flavonoid that has been found to inhibit cell proliferation by arresting the cell cycle at the G2/M phase. Inhibition of growth through cell cycle arrest and induction of apoptosis appear to be related to induction of p53.Inhibits PMA-mediated tumor promotion by inhibiting protein kinase C1 and the resulting suppression of oncogene expression. It has also been reported to inhibit topoisomerase I-catalyzed DNA re-ligation and enhance gap junctional intercellular communication. |
Sigma Aldrich -
A3145
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Biochem/physiol Actions A plant flavonoid that has been found to inhibit cell proliferation by arresting the cell cycle at the G2/M phase. Inhibition of growth through cell cycle arrest and induction of apoptosis appear to be related to induction of p53.Inhibits PMA-mediated tumor promotion by inhibiting protein kinase C1 and the resulting suppression of oncogene expression. It has also been reported to inhibit topoisomerase I-catalyzed DNA re-ligation and enhance gap junctional intercellular communication. |
Sigma Aldrich -
10798
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Other Notes Inhibitor of human estrogen synthetase2 Biochem/physiol Actions A plant flavonoid that has been found to inhibit cell proliferation by arresting the cell cycle at the G2/M phase. Inhibition of growth through cell cycle arrest and induction of apoptosis appear to be related to induction of p53.Inhibits PMA-mediated tumor promotion by inhibiting protein kinase C1 and the resulting suppression of oncogene expression. It has also been reported to inhibit topoisomerase I-catalyzed DNA re-ligation and enhance gap junctional intercellular communication. |
REFERENCES
REFERENCES
From Suppliers
Google Scholar
PubMed
Google Books
- • Si D et al. Drug Metab Dispos. 2009 Mar;37(3):629-34.
- • Ding, J, et al.: J. Chrom B Anal. Technol. Biomed. Life Sci., 895, 108 (2012)
- • Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 919B, (nmr)
- • Aldrich Library of Infrared Spectra, 3rd edn., 1981, 906A, (ir)
- • Seikel, M.J., J.A.C.S., 1955, 77, 5685, (derivs)
- • Kovalev, I.P. et al., Zh. Obshch. Khim., 1963, 33, 1670, (ir)
- • Batterham, T.J. et al., Aust. J. Chem., 1964, 17, 428, (pmr)
- • Nowicka-Jankowska, T. et al., Chem. Anal. (Warsaw), 1965, 10, 129, (detn, Al, rare earths)
- • Audier, H., Bull. Soc. Chim. Fr., 1966, 2892, (ms)
- • Nogradi, M. et al., Chem. Ber., 1967, 100, 2783, (synth)
- • Wagner, H. et al., Tet. Lett., 1968, 1635, (synth)
- • Chopin, J. et al., C. R. Hebd. Seances Acad. Sci., 1969, 268, 980, (isol)
- • Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, 1449, (occur)
- • Khane, V.B. et al., Indian J. Chem., 1974, 12, 1134, (synth)
- • Wollenweber, E., Phytochemistry, 1974, 13, 2318; 1975, 15, 438; 2013; 1977, 16, 295, (occur)
- • Okigawa, M. et al., J.C.S. Perkin 1, 1975, 1563, (pmr)
- • Wagner, H. et al., Tet. Lett., 1976, 1799, (cmr)
- • Gaydou, E.M. et al., Bull. Soc. Chim. Fr., 1978, 43, (synth, cmr, uv)
- • Yiwan, J. et al., Org. Mass Spectrom., 1978, 13, 167, (ms)
- • Tamura, H. et al., Tet. Lett., 1983, 24, 5749
- • Besson, E. et al., Phytochemistry, 1984, 23, 159, (isol, bibl)
- • Loo, P.V. et al., Magn. Reson. Chem., 1986, 24, 879, (pmr, cmr)
- • Srivastava, S. et al., Indian J. Chem., Sect. B, 1987, 26, 57, (synth)
- • Plant Flavonoids in Biology and Medicine II, (eds. Cody V. et al), A.R. Liss, N.Y., 1988, 251
- • The Flavonoids: Advances in Research since 1980, (Ed. Harborne, J.B.), Chapman and Hall, London, 1988
- • Nagarathnam, D. et al., J.O.C., 1991, 56, 4884, (synth)
- • Gothelf, K. et al., Acta Chem. Scand., 1992, 46, 494; 1994, 48, 61, (synth, pmr)
- • Shen, C.-C. et al., Phytochemistry, 1993, 34, 843, (pmr, cmr)
- • Roth, L. et al., Roth Collection of Natural Product Data, VCH, Weinheim, 1995
- • Ramsewak, R.S. et al., J. Nat. Prod., 1999, 62, 1558-1561, (Dirca palustris derivs)
- • Manthey, J.A. et al., Curr. Med. Chem., 2001, 8, 135-153, (rev, activity)
- • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CDH250
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PATENTS
PATENTS
PubChem Patent
Google Patent