Apigenin

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Apigenin are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Apigenin?

The molecule Apigenin presents a molecular formula of C15H10O5 and its IUPAC name is 5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one.

Apigenin is a naturally occurring plant flavonoid that has been shown to have a number of potential health benefits. It belongs in a variety of plants, including chamomile, parsley, and celery, and is also present in certain fruits, such as apples and grapes..

One of the main potential benefits of apigenin is its antioxidant properties. Antioxidants help to neutralize harmful free radicals in the body, which can damage cells and contribute to the development of diseases such as cancer and heart disease. By neutralizing free radicals, antioxidants like apigenin may help to protect against these diseases..

Apigenin has also been shown to have anti-inflammatory properties, which means it may be able to reduce inflammation in the body. Inflammation is a normal immune response to injury or infection, but chronic inflammation can contribute to the development of a number of diseases, including cancer and heart disease. By reducing inflammation, apigenin may be able to help prevent these diseases..

In addition to its antioxidant and anti-inflammatory properties, apigenin has also been shown to have potential benefits for brain health. It has been shown to have a protective effect on brain cells and may help to improve memory and cognitive function..

Apigenin is often used in supplements and is also found in certain foods, such as chamomile tea and parsley. It is generally considered safe, with few reported side effects. However, as with any supplement, it is important to speak with a healthcare provider before starting to use apigenin..

Summary

From all the above, this molecule is a naturally occurring plant flavonoid with potential health benefits, including antioxidant and anti-inflammatory properties. It may also have potential benefits for brain health. While it is generally considered safe, it is always important to speak with a healthcare provider before starting to use any new supplement..

3D structure

Cartesian coordinates

Geometry of Apigenin in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Apigenin KZNIFHPLKGYRTM-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Apigenin

 

Molecule descriptors

 
IUPAC name5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
InChI codeInChI=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
InChI KeyKZNIFHPLKGYRTM-UHFFFAOYSA-N
SMILESc1cc(ccc1c1cc(=O)c2c(cc(cc2o1)O)O)O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • 2-(p-Hydroxyphenyl)-5,7-dihydroxychromone
  • 20A365
  • 3cf9
  • 4 inverted exclamation mark ,5,7-trihydroxyflavone
  • 4',5,7-Trihydroxyflavone
  • 4',5,7-Trihydroxyflavone;Apigenol;C.I. Natural Yellow 1
  • 4',5,7-trihydroxy-Flavone
  • 4',7-Trihydroxyflavone
  • 4,5, 7-Trihydroxyflavone
  • 4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxyphenyl)-
  • 4H-1-Benzopyran-4-one,7-dihydroxy-2-(4-hydroxyphenyl)-
  • 4der
  • 4dgm
  • 4hkk
  • 4′,5,7-Trihydroxyflavone
  • 5,7,4'-Trihydroxyflavone
  • 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone
  • 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
  • 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
  • 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one #
  • 5,7-dihydroxy-2-(4-hydroxyphenyl)-chromen-4-one
  • 5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
  • 520-36-5
  • 7V515PI7F6
  • 8002-66-2
  • A 3145
  • A828903
  • AC-8011
  • ACon1_002450
  • APEGENIN
  • Apigenin
  • Apigenin, 13
  • Apigenin; 4',5,7-Trihydroxyflavone
  • Apigenine
  • Apigenol
  • BBL010499
  • BCP28288
  • BDBM7458
  • BIDD:ER0135
  • BPBio1_000406
  • BRN 0262620
  • BSPBio_000368
  • BSPBio_003384
  • Bio1_000376
  • Bio1_000865
  • Bio1_001354
  • Biochem Biophys Res Comm 212: 767 (1997)
  • BiomolKI2_000082
  • BiomolKI_000078
  • C.I. Natural Yellow 1
  • C01477
  • CCG-40061
  • CCRIS 3789
  • CI NATURAL YELLOW 1
  • CS-5432
  • Chamomile
  • Chamomile Powder
  • D50A2D8A-6D8B-4708-B21E-2DE9580D033F
  • DB07352
  • DSSTox_CID_2391
  • DSSTox_GSID_22391
  • DSSTox_RID_76568
  • DivK1c_000798
  • EU-0100065
  • FLAVONE, 4',5,7-TRIHYDROXY-
  • FT-0622445
  • FT-0623582
  • FT-0662251
  • GTPL4136
  • HMS1569C10
  • HMS1922P22
  • HMS2096C10
  • HMS2230D17
  • HMS3260M11
  • HMS3267D21
  • HMS3373B18
  • HMS3412A08
  • HMS3561P09
  • HMS3655D18
  • HMS3676A08
  • HMS3866D03
  • HMS502H20
  • HSCI1_000221
  • HSDB 7573
  • HY-N1201
  • IDI1_000798
  • K00045
  • KBio1_000798
  • KBio3_002887
  • KBioGR_002565
  • LMPK12110005
  • LP00065
  • LY 080400
  • LY-080400
  • Lopac-A-3145
  • Lopac0_000065
  • MEGxp0_000176
  • MFCD00006831
  • MLS000697626
  • MLS000859991
  • MLS001074874
  • MLS006011839
  • Matricaria oil
  • N1828
  • NCGC00015049-01
  • NCGC00015049-02
  • NCGC00015049-03
  • NCGC00015049-04
  • NCGC00015049-05
  • NCGC00015049-06
  • NCGC00015049-07
  • NCGC00015049-08
  • NCGC00015049-09
  • NCGC00015049-10
  • NCGC00015049-11
  • NCGC00015049-12
  • NCGC00015049-13
  • NCGC00015049-14
  • NCGC00015049-15
  • NCGC00015049-16
  • NCGC00015049-18
  • NCGC00015049-28
  • NCGC00025057-01
  • NCGC00025057-02
  • NCGC00025057-03
  • NCGC00025057-04
  • NCGC00025057-05
  • NCGC00025057-06
  • NCGC00025057-07
  • NCGC00025057-08
  • NCGC00025057-09
  • NCGC00169835-01
  • NCGC00169835-02
  • NCGC00169835-03
  • NCGC00256419-01
  • NCGC00259092-01
  • NCGC00260750-01
  • NCI60_041830
  • ND-9076
  • NINDS_000798
  • NSC 83244
  • NSC-815095
  • NSC-83244
  • NSC815095
  • NSC83244
  • Naringenin, 18
  • O11338
  • Oprea1_622293
  • PELARGIDENON-1449
  • Pelargidenon 1449
  • Pelargidenone
  • Prestwick0_000414
  • Prestwick1_000414
  • Prestwick2_000414
  • Prestwick3_000414
  • Prestwick_719
  • Q-100586
  • Q-200822
  • Q424567
  • SDCCGMLS-0066379.P001
  • SDCCGSBI-0050053.P003
  • SMP2_000338
  • SMR000326850
  • SPECTRUM200846
  • SR-01000075663
  • SR-01000075663-1
  • SR-01000075663-3
  • SR-01000075663-7
  • SR-01000075663-8
  • ST056301
  • STK801630
  • SW196866-2
  • SY005957
  • Spigenin
  • TS-00897
  • Tocris-1227
  • UCCF 031
  • UCCF-031
  • Versulin
  • ZB1873
  • apigenin
  • cid_5280443
  • ghl.PD_Mitscher_leg0.1194
  • s2262

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3871576
  • CAS-520-36-5
  • UNII-7V515PI7F6
  • AKOS002140699
  • BRD-K01493881-001-10-4
  • BRD-K01493881-001-17-9
  • DTXSID6022391
  • CHEMBL28
  • CHEBI:18388
  • Tox21_201542
  • Tox21_302884
  • Tox21_500065
  • EINECS 208-292-3
  • SPBio_000416
  • SPBio_002307
  • SCHEMBL19428
  • SCHEMBL222227
  • Spectrum2_000428
  • Spectrum3_001882
  • Spectrum4_001999

Physico-Chemical properties

IUPAC name5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Molecular formulaC15H10O5
Molecular weight270.24
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity74.0
LogP1.7
Topological polar surface area90.9

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.