CAS 520-36-5|CAS 520-36-5|5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one|5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one|chamomile|Apigenin|4',5,7-Trihydroxyflavone|C.I. Natural Yellow 1|Apig...

General Information

Structure

Molecular Formula

C₁₅H₁₀O₅

Molecular Mass

270.2369

Exact Mass

270.05282342

Charge

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

Canonic Smiles

Oc1ccc(cc1)c1cc(=O)c2c(o1)cc(cc2O)O

Isomeric Smiles

c1cc(O)ccc1c1oc2c(c(=O)c1)c(cc(c2)O)O

Calculated Properties

JChem

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

Polarizability

27.10717

Polar Surface Area

86.99

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

3.07

LOG S

-3.36

Solubility (Water)

1.18e-01 g/l

Data Source

Names and Identifiers

IUPAC name

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Synonyms

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-oneApigenin4',5,7-TrihydroxyflavoneC.I. Natural Yellow 1ApigenineSpigeninApigenolChamomileVersulin4′,5,7-TrihydroxyflavoneApigenin4',5,7-三羟基黄酮4',5,7-TrihydroxyflavoneApigeninN-[4-(1-Cyanocyclopentyl)phenyl]-2-[[(1-oxido-4-pyridinyl)methyl]amino]-3-pyridinecarboxamideApatinib 25-N-Oxide HydrochloridePelargidenone

IUPAC Traditional name

chamomile 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Names and Identifiers

Registration numbers

EC Number

CAS Number

MDL Number

Beilstein Number

Merck Index

PubChem SID

994438232427821216096843524846790

CHEMBL

Chemspider ID

PubChem CID

KEGG ID

Wikipedia Title

CHEBI ID

DrugBank ID

Registration numbers

Properties

Product Information

Free Base

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from parsley

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

Pharmacology Properties

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)

Tyrosine kinase inhibitor

Properties

Related Proteins

No Data Available

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Molecular Spectra

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Molecule Details

Selleck Chemicals

S2262

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

Apollo Scientific

OR7265T

A MAP kinase inhibitor. Also inhibits the proliferation of malignant tumor cells.

Sigma Aldrich

A281

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.

A3145

460745

42251

10793

10798

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.

Wikipedia

Apigenin

TRC

A726160

Apatinib 25-N-Oxide is a metabolite of the antiangiogenic agent and selective VEGFR2 inhibitor Apatinib (A726150).

DrugBank

DB07352

Drug information: experimental

Molecule Details

References

PubChem Literature

From Data Sources

• 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)

• Yiwan, J. et al., Org. Mass Spectrom., 1978, 13, 167, (ms)

• Seikel, M.J., J.A.C.S., 1955, 77, 5685, (derivs)

• Roth, L. et al., Roth Collection of Natural Product Data, VCH, Weinheim, 1995

• Nowicka-Jankowska, T. et al., Chem. Anal. (Warsaw), 1965, 10, 129, (detn, Al, rare earths)

• Nogradi, M. et al., Chem. Ber., 1967, 100, 2783, (synth)

• Wagner, H. et al., Tet. Lett., 1976, 1799, (cmr)

• Plant Flavonoids in Biology and Medicine II, (eds. Cody V. et al), A.R. Liss, N.Y., 1988, 251

• Tamura, H. et al., Tet. Lett., 1983, 24, 5749

• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, 1449, (occur)

• Gaydou, E.M. et al., Bull. Soc. Chim. Fr., 1978, 43, (synth, cmr, uv)

• Nagarathnam, D. et al., J.O.C., 1991, 56, 4884, (synth)

• Ramsewak, R.S. et al., J. Nat. Prod., 1999, 62, 1558-1561, (Dirca palustris derivs)

• 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)

• The Flavonoids: Advances in Research since 1980, (Ed. Harborne, J.B.), Chapman and Hall, London, 1988

• Wagner, H. et al., Tet. Lett., 1968, 1635, (synth)

• Aldrich Library of Infrared Spectra, 3rd edn., 1981, 906A, (ir)

• Kovalev, I.P. et al., Zh. Obshch. Khim., 1963, 33, 1670, (ir)

• Srivastava, S. et al., Indian J. Chem., Sect. B, 1987, 26, 57, (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)

• Chopin, J. et al., C. R. Hebd. Seances Acad. Sci., 1969, 268, 980, (isol)

• Besson, E. et al., Phytochemistry, 1984, 23, 159, (isol, bibl)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 919B, (nmr)

• Audier, H., Bull. Soc. Chim. Fr., 1966, 2892, (ms)

• Khane, V.B. et al., Indian J. Chem., 1974, 12, 1134, (synth)

• Batterham, T.J. et al., Aust. J. Chem., 1964, 17, 428, (pmr)

• Manthey, J.A. et al., Curr. Med. Chem., 2001, 8, 135-153, (rev, activity)

• Loo, P.V. et al., Magn. Reson. Chem., 1986, 24, 879, (pmr, cmr)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CDH250

References

Bioactivity

PubChem BioAssay

Bioactivity