Compound: apigenin
SMILES: O=c1c2c(oc(c1)-c3ccc(O)cc3)cc(O)cc2O
InChIKey: KZNIFHPLKGYRTM-UHFFFAOYSA-N
Synonyms: apigenin, 520-36-5, 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one, Versulin, Apigenol, 4',5,7-Trihydroxyflavone, Apigenine, Spigenin, C.I. Natural Yellow 1, 5,7,4'-Trihydroxyflavone, 5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one, 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, Pelargidenon 1449, 4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxyphenyl)-, 2-(p-Hydroxyphenyl)-5,7-dihydroxychromone, 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone, DTXSID6022391, FLAVONE, 4',5,7-TRIHYDROXY-, CHEBI:18388, 7V515PI7F6, NSC-83244, DTXCID902391, UCCF-031, LY-080400, RefChem:6383, 208-292-3, MFCD00006831, Chamomile oil, german, UCCF 031, NSC 83244, CHEMBL28, NSC83244, CAS-520-36-5, ST056301, M01289, 4',5,7-Trihydroxyflavone;Apigenol;C.I. Natural Yellow 1, SMR000326850, CCRIS 3789, SR-01000075663, EINECS 208-292-3, BRN 0262620, Pelargidenone;, UNII-7V515PI7F6, Apigenol;, HSDB 7573, 4der, 4dgm, 4hkk, Chamomile Absolute, Naringenin, 18, 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;     4',5,7-Trihydroxyflavone; Pelargidenon 1449;, Prestwick_719, Apigenin, 13, Apigenin (Standard), APEGENIN, Apigenin - 94%, Apigenin - 97%, ACACETIN_met001, Tocris-1227, 3cf9, APIGENIN [HSDB], 4',7-Trihydroxyflavone, APIGENIN [MI], BiomolKI_000078, Prestwick0_000414, Prestwick1_000414, Prestwick2_000414, Prestwick3_000414, Spectrum2_000428, Spectrum3_001882, Spectrum4_001999, Lopac-A-3145, 4,5,7-Trihydroxyflavone, APIGENIN [USP-RS], APIGENIN [WHO-DD], BiomolKI2_000082, Epitope ID:613414, 4,5, 7-Trihydroxyflavone, PELARGIDENON-1449, CI NATURAL YELLOW 1, Lopac0_000065, Oprea1_622293, SCHEMBL19428, 4',5,7-trihydroxy-Flavone, Apigenin, analytical standard, BSPBio_000368, BSPBio_003384, KBioGR_002565, SPECTRUM200846, 5-18-04-00574 (Beilstein Handbook Reference), MLS000697626, MLS000859991, MLS001074874, MLS006011839, BIDD:ER0135, DivK1c_000798, SCHEMBL222227, SPBio_000416, SPBio_002307, ghl.PD_Mitscher_leg0.1194, BDBM7458, BPBio1_000406, GTPL4136, MEGxp0_000176, orb1306215, orb3025913, SCHEMBL29351464, ACon1_002450, cid_5280443, HMS502H20, HY-N1201R, KBio1_000798, KBio3_002887, MSK7405, NINDS_000798, Bio1_000376, Bio1_000865, Bio1_001354, HMS1569C10, HMS1922P22, HMS2096C10, HMS2230D17, HMS3260M11, HMS3267D21, HMS3373B18, HMS3412A08, HMS3561P09, HMS3655D18, HMS3676A08, HMS3866D03, HMS5080C22, Apigenin, >=95.0% (HPLC), HY-N1201, Tox21_201542, Tox21_302884, Tox21_500065, Apigenin; 4',5,7-Trihydroxyflavone, BBL010499, CCG-40061, EBC-17043, HB0117, HSCI1_000221, LMPK12110005, NSC815095, s2262, SBB066087, STK801630, ZB1873, AKOS002140699, AC-8011, CS-5432, DB07352, FA16099, LP00065, ND-9076, NSC-815095, SDCCGMLS-0066379.P001, SDCCGSBI-0050053.P003, SDCCGSBI-0050053.P011, IDI1_000798, SMP2_000338, Apigenin, >=97% (TLC), from citrus, 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, NCGC00015049-22, 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, FA159894, LY080400, NCI60_041830, SY005957, TS-00897, A1514, EU-0100065, NS00007770, SW196866-2, A 3145, C01477, K00045, O11338, Apigenin 100 microg/mL in Acetonitrile:Methanol, Apigenin, >=97% (TLC), from parsley, powder, Biochem Biophys Res Comm 212: 767 (1997), EN300-7382221, 5,7-dihydroxy-2-(4-hydroxyphenyl)-chromen-4-one, APIGENIN (CONSTITUENT OF CHAMOMILE) [DSC], Apigenin, primary pharmaceutical reference standard, Q424567, SR-01000075663-1, SR-01000075663-3, SR-01000075663-7, SR-01000075663-8, BRD-K01493881-001-10-4, BRD-K01493881-001-17-9, BRD-K01493881-001-28-6, BRD-K01493881-001-29-4, 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one #, Z1741982550, 4H-1-Benzopyran-4-one,7-dihydroxy-2-(4-hydroxyphenyl)-, D50A2D8A-6D8B-4708-B21E-2DE9580D033F, Apigenin, United States Pharmacopeia (USP) Reference Standard
Theoretical properties:
molecular_formula: C15H10O5
molecular_weight: 270.24 g/mol
exact_mass: 270.05282342 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 1
heavy_atom_count: 20
topological_polar_surface_area: 87 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Yellow needles from aqueous pyridine
color: Yellow needles from aqueous pyridine
melting_point: 345-350 °C
solubility: Soluble in ethanol, pyridine, concentrated sulfuric acid; very soluble in dilute alkalies
Descriptions:
pubchem: Apigenin is a trihydroxyflavone that is flavone substituted by hydroxy groups at positions 4', 5 and 7. It induces autophagy in leukaemia cells. It has a role as a metabolite and an antineoplastic agent. It is a conjugate acid of an apigenin-7-olate.
chebi: A trihydroxyflavone that is flavone substituted by hydroxy groups at positions 4', 5 and 7.  It induces autophagy in leukaemia cells.
chembl: APIGENIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Apigenin (4′,5,7-trihydroxyflavone), found in many plants, is a flavone compound that is the aglycone of several naturally occurring glycosides. It is a yellow crystalline solid that has been used to dye wool.
Apigenin is abundant in parsley, celery, celeriac, and chamomile flowers. It occurs in many fruits and vegetables, with the highest concentrations in dried and fresh parsley.