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520-36-5 molecular structure
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5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

ChemBase ID: 5003
Molecular Formular: C15H10O5
Molecular Mass: 270.2369
Monoisotopic Mass: 270.05282342
SMILES and InChIs

SMILES:
c1cc(O)ccc1c1oc2c(c(=O)c1)c(cc(c2)O)O
Canonical SMILES:
Oc1ccc(cc1)c1cc(=O)c2c(o1)cc(cc2O)O
InChI:
InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H
InChIKey:
KZNIFHPLKGYRTM-UHFFFAOYSA-N

Cite this record

CBID:5003 http://www.chembase.cn/molecule-5003.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
IUPAC Traditional name
chamomile
5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
Synonyms
5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
4',5,7-Trihydroxyflavone
N-[4-(1-Cyanocyclopentyl)phenyl]-2-[[(1-oxido-4-pyridinyl)methyl]amino]-3-pyridinecarboxamide
Apatinib 25-N-Oxide Hydrochloride
Apigenine
Chamomile
Apigenol
Spigenin
Versulin
C.I. Natural Yellow 1
4′,5,7-Trihydroxyflavone
Apigenin
Apigenin
Apigenin
4',5,7-Trihydroxyflavone
Pelargidenone
4',5,7-三羟基黄酮
CAS Number
520-36-5
520-36-5
EC Number
208-292-3
MDL Number
MFCD00006831
Beilstein Number
262620
Merck Index
14730
PubChem SID
99443823
160968435
24846790
24278212
PubChem CID
5280443
CHEBI ID
18388
CHEMBL
28
Chemspider ID
4444100
DrugBank ID
DB07352
KEGG ID
C01477
Wikipedia Title
Apigenin

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 6.574692  H Acceptors
H Donor LogD (pH = 5.5) 2.671756 
LogD (pH = 7.4) 1.7656507  Log P 2.7066891 
Molar Refractivity 72.9139 cm3 Polarizability 27.10717 Å3
Polar Surface Area 86.99 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 3.07  LOG S -3.36 
Solubility (Water) 1.18e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
1 M KOH: soluble50 mg/mL expand Show data source
DMSO: soluble27 mg/mL expand Show data source
H2O: insoluble expand Show data source
Apperance
Yellow crystalline solid expand Show data source
yellow powder expand Show data source
Yellow powder expand Show data source
yellow to green expand Show data source
Melting Point
>300 °C(lit.) expand Show data source
300°C expand Show data source
345–350 °C expand Show data source
ca 315°C dec. expand Show data source
Density
0.905 g/ml expand Show data source
Storage Condition
-20°C expand Show data source
Storage Warning
Irritant expand Show data source
RTECS
LK9276000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
26-37 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
-20°C expand Show data source
2-8°C expand Show data source
Gene Information
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) expand Show data source
Mechanism of Action
Tyrosine kinase inhibitor expand Show data source
Purity
≥75% (HPLC) expand Show data source
≥95.0% (HPLC) expand Show data source
≥97% (TLC) expand Show data source
≥99% (HPLC) expand Show data source
95% expand Show data source
97% expand Show data source
99.0 expand Show data source
Grade
analytical standard expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Impurities
~2% water expand Show data source
<5% acetic acid expand Show data source
≤2% water expand Show data source
Biological Source
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 expand Show data source
from parsley expand Show data source
Shelf Life
(limited shelf life, expiry date on the label) expand Show data source
Application(s)
Antispasmolytic agent expand Show data source
Shows antineoplastic activity in vitro expand Show data source
Empirical Formula (Hill Notation)
C15H10O5 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Apollo Scientific Apollo Scientific Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB07352 external link
Drug information: experimental
Apollo Scientific Ltd - OR7265T external link
A MAP kinase inhibitor. Also inhibits the proliferation of malignant tumor cells.
Selleck Chemicals - S2262 external link
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 external link
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 external link
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 external link
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 external link
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 external link
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 external link
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.
Toronto Research Chemicals - A726160 external link
Apatinib 25-N-Oxide is a metabolite of the antiangiogenic agent and selective VEGFR2 inhibitor Apatinib (A726150).

REFERENCES

REFERENCES

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