Marvin  02180812302D          

 20 22  0  0  0  0            999 V2000
    0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 13  1  2  0  0  0  0
  1  2  1  0  0  0  0
  4  3  2  0  0  0  0
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
 12  6  1  0  0  0  0
  7  5  2  0  0  0  0
 11  7  1  0  0  0  0
  8  6  2  0  0  0  0
  8  7  1  0  0  0  0
  2  9  2  0  0  0  0
  9 14  1  0  0  0  0
 10  9  1  0  0  0  0
  3 10  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  2  0  0  0  0
 17 15  2  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 19 18  2  0  0  0  0
 20 19  1  0  0  0  0
M  END
> <ID>
CHEBI:18388

> <NAME>
apigenin

> <DEFINITION>
A trihydroxyflavone that is flavone substituted by hydroxy groups at positions 4', 5 and 7.  It induces autophagy in leukaemia cells.

> <STAR>
3

> <SECONDARY_ID>
CHEBI:12084; CHEBI:2768; CHEBI:22588

> <SYNONYM>
versulin; spigenin; chamomile; C.I. Natural Yellow 1; Apigenin; 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 5,7-dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone; 5,7,4'-Trihydroxyflavone; 4',5,7-Trihydroxyflavone; 2-(p-hydroxyphenyl)-5,7-dihydroxychromone

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

> <FORMULA>
C15H10O5

> <MASS>
270.23690

> <MONOISOTOPIC_MASS>
270.05282

> <CHARGE>
0

> <SMILES>
Oc1ccc(cc1)-c1cc(=O)c2c(O)cc(O)cc2o1

> <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

> <BEILSTEIN_REGISTRY_NUMBER>
262620

> <CAS_REGISTRY_NUMBER>
520-36-5

> <REAXYS_REGISTRY_NUMBER>
262620

> <CHEMIDPLUS>
520-36-5

> <KEGG_COMPOUND_ACCESSION>
C01477

> <KNAPSACK_ACCESSION>
C00003817

> <LINCS_ACCESSION>
LSM-5206

> <LIPID_MAPS_INSTANCE_ACCESSION>
LMPK12110005

> <METACYC_ACCESSION>
CPD-431

> <PDBECHEM_ACCESSION>
AGI

> <WIKIPEDIA_ACCESSION>
Apigenin

> <PUBMED_CITATION>
23304222; 23344191; 23354402; 23359392; 28166217

$$$$