Apigenin






Names

    • A1514
    • SPBio_000416
    • APEGENIN
    • NCGC00015049-14
    • HMS3676A08
    • CHEMBL28
    • Z1741982550
    • SR-01000075663-1
    • MFCD00006831
    • NCGC00015049-05
    • Apigenin (Standard)
    • NCGC00015049-22
    • Q-200822
    • Apigenine
    • HMS3412A08
    • NCGC00015049-16
    • APIGENIN [WHO-DD]
    • 4,5, 7-Trihydroxyflavone
    • HMS502H20
    • D50A2D8A-6D8B-4708-B21E-2DE9580D033F
    • UCCF-031
    • SPBio_002307
    • Oprea1_622293
    • HMS3373B18
    • NCGC00015049-02
    • 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
    • 4dgm
    • AKOS002140699
    • SY005957
    • ACACETIN_met001
    • 4H-1-Benzopyran-4-one,7-dihydroxy-2-(4-hydroxyphenyl)-
    • CAS-520-36-5
    • Lopac-A-3145
    • SDCCGSBI-0050053.P003
    • Apigenin, >=97% (TLC), from citrus
    • NCGC00025057-09
    • NCGC00025057-08
    • 5,7-dihydroxy-2-(4-hydroxyphenyl)-chromen-4-one
    • Q-100586
    • NCGC00169835-01
    • ND-9076
    • KBio1_000798
    • NCGC00025057-04
    • Prestwick2_000414
    • Apigenin, >=95.0% (HPLC)
    • A 3145
    • NS00007770
    • NSC-815095
    • Prestwick0_000414
    • HMS3267D21
    • NCI60_041830
    • NCGC00015049-13
    • CCG-40061
    • SR-01000075663-7
    • MLS000859991
    • HSDB 7573
    • Prestwick1_000414
    • NCGC00169835-02
    • BRD-K01493881-001-10-4
    • SPECTRUM200846
    • BIDD:ER0135
    • SCHEMBL19428', "4',5,7-trihydroxy-Flavone", 'Apigenin, analytical standard
    • CI NATURAL YELLOW 1
    • HMS3655D18
    • TS-00897
    • Apigenin, >=97% (TLC), from parsley, powder
    • LP00065
    • MLS006011839
    • ACon1_002450
    • 4der
    • 2-(P-HYDROXYPHENYL)-5,7-DIHYDROXY-CHROMONE
    • Chamomile', "4',5,7-Trihydroxyflavone", 'Spigenin
    • NSC-83244
    • apigenin
    • EINECS 208-292-3
    • NCGC00015049-09
    • Versulin
    • Biochem Biophys Res Comm 212: 767 (1997)
    • 2-(p-Hydroxyphenyl)-5,7-dihydroxychromone
    • Bio1_001354
    • NCGC00025057-02
    • NCGC00015049-28
    • NCGC00015049-06
    • BiomolKI_000078
    • 4hkk
    • NSC815095
    • NCGC00260750-01
    • EN300-7382221
    • SR-01000075663-3
    • BRD-K01493881-001-17-9
    • KBio3_002887
    • IDI1_000798
    • UNII-7V515PI7F6
    • SCHEMBL222227
    • O11338
    • BSPBio_003384
    • Chamomile oil, german
    • Prestwick3_000414
    • BPBio1_000406
    • SDCCGMLS-0066379.P001
    • BRD-K01493881-001-28-6
    • KBioGR_002565
    • HMS1922P22
    • DTXSID6022391
    • PELARGIDENON-1449
    • NCGC00025057-06
    • NCGC00025057-01
    • UCCF 031
    • Spectrum3_001882
    • LY-080400', "4',5,7-Trihydroxyflavone;Apigenol;C.I. Natural Yellow 1", 'SMR000326850
    • DivK1c_000798
    • BDBM7458
    • NCGC00015049-10
    • Apigenin, primary pharmaceutical reference standard
    • s2262
    • HMS2230D17
    • SDCCGSBI-0050053.P011
    • HB0117
    • NCGC00015049-08
    • LMPK12110005
    • Lopac0_000065
    • AC-8011
    • C.I. Natural Yellow 1
    • NSC 83244
    • Tox21_201542
    • NCGC00259092-01
    • SR-01000075663-8
    • NCGC00015049-11
    • BSPBio_000368
    • Naringenin, 18', "5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 4',5,7-Trihydroxyflavone; Pelargidenon 1449;", 'Prestwick_719
    • MLS000697626
    • MLS001074874
    • NSC83244
    • 3cf9
    • Spectrum2_000428
    • BCP28288
    • NCGC00015049-07
    • DTXCID902391
    • HY-N1201
    • APIGENIN (CONSTITUENT OF CHAMOMILE) [DSC]
    • HMS3866D03
    • GTPL4136
    • HMS3561P09
    • 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone
    • Spectrum4_001999
    • NCGC00015049-15
    • NCGC00256419-01
    • 7V515PI7F6
    • cid_5280443
    • NCGC00025057-07
    • 4H-1BENZOPYRAN-4-ONE,5,7-DIHYDROXY-2-(4-HYDROXY-PHENYL)-', "C.I. Natural Yellow 1 , 4',5,7-Trihydroxyflavone , NSC 83244 , Apigenol , LY 080400"
    • BiomolKI2_000082
    • SR-01000075663
    • EU-0100065
    • Apigenin 100 microg/mL in Acetonitrile:Methanol
    • NINDS_000798
    • 4′,5,7-Trihydroxyflavone
    • Bio1_000865
    • NCGC00025057-03
    • K00045
    • M01289
    • HSCI1_000221
    • LY080400
    • HMS1569C10
    • 4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxyphenyl)-
    • C01477
    • NCGC00025057-05
    • NCGC00015049-01
    • ghl.PD_Mitscher_leg0.1194
    • NCGC00169835-03
    • Tox21_302884
    • Apigenin
    • Tox21_500065', "Apigenin; 4',5,7-Trihydroxyflavone", 'BBL010499
    • NCGC00015049-18
    • Bio1_000376
    • APIGENIN (CONSTITUENT OF CHAMOMILE)
    • SW196866-2
    • NCGC00015049-12
    • 5-18-04-00574 (Beilstein Handbook Reference)
    • Apigenin, 13
    • STK801630
    • CCRIS 3789', "FLAVONE, 4',5,7-TRIHYDROXY-", 'CHEBI:18388
    • Apigenol
    • APIGENIN [USP-RS]
    • NCGC00015049-04
    • BRD-K01493881-001-29-4
    • 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
    • MEGxp0_000176
    • Apigenin, United States Pharmacopeia (USP) Reference Standard
    • DB07352
    • Q424567
    • 520-36-5
    • Tocris-1227
    • 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one #
    • ST056301
    • ZB1873
    • HY-N1201R
    • NCGC00015049-03
    • HMS3260M11
    • APIGENIN [HSDB]', "4',7-Trihydroxyflavone", 'APIGENIN [MI]
    • SMP2_000338
    • HMS2096C10
    • BRN 0262620
    • CS-5432
    • Pelargidenon 1449', "5,7,4'-Trihydroxyflavone", '5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

Attributes

  • Canonical SMILES

    C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)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

  • Molecule Class: Flavonoids
  • TPSA: 90.9
  • #RotBonds: 1
  • MW: 270.23999999999995
  • HBD: 3
  • HBA: 5
  • logP: 2.5768000000000018
  • Chemical Formula: C15H10O5


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. pandacaqui Cuba, Thailand 761085 -

External Databases


References

  • Acetylcholinesterase Inhibitor From Tabernaemontana pandacaqui Flowers Natural Product Communications, 2020 (DOI).

Compound-Protein Relationships


Compound Activities

    • Acetylcholinesterase inhibitory

Predicted NMR Spectral Data


Predicted MS Fragmentation Pattern

    N.B.: It is recommended to zoom in on a specific area of an MS plot before hovering on a peak.

Predicted ADMET Properties

    Category Property Name Predicted Value
    Absorption Caco-2 (logPaap) -4.95
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.95
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -0.46
    Distribution Blood-Brain Barrier (Central Nervous System) -2.06
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.81
    Plasma Protein Binding 83.17
    Steady State Volume of Distribution 0.37
    Metabolism Breast Cancer Resistance Protein Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Non-Substrate
    CYP 2C19 Inhibitor Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor Inhibitor
    CYP 2C9 Substrate Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Inhibitor
    CYP 3A4 Substrate Non-Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 4.07
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Safe
    Bioconcentration Factor 1.3
    Biodegradation Safe
    Carcinogenesis Toxic
    Crustacean Toxic
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Toxic
    Maximum Tolerated Dose 1.44
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 4.67
    Micronucleos Toxic
    NR-AhR Toxic
    NR-AR Safe
    NR-AR-LBD Safe
    NR-Aromatase Safe
    NR-ER Toxic
    NR-ER-LBD Toxic
    NR-GR Toxic
    NR-PPAR-gamma Safe
    NR-TR Safe
    T. Pyriformis 3.73
    Rat (Acute) 2.14
    Rat (Chronic Oral) 2.75
    Fathead Minnow 4.47
    Respiratory Disease Safe
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Toxic
    SR-p53 Toxic
    General Properties Boiling Point 467.6
    Hydration Free Energy -12.88
    Log(D) at pH=7.4 3.26
    Log(P) 3.18
    Log S -4.32
    Log(Vapor Pressure) -8.69
    Melting Point 330.43
    pKa Acid 6.72
    pKa Basic 6.8