5,7-Dihydroxy-2-(4-hydroxy-phenyl)-3-methoxy-chromen-4-one

ID: ALA165064

Cas Number: 1592-70-7

PubChem CID: 5280862

Product Number: I167641, Order Now?

Max Phase: Preclinical

Molecular Formula: C16H12O6

Molecular Weight: 300.27

Molecule Type: Small molecule

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Associated Items:

Names and Identifiers

Synonyms: Isokaempferide | Kaempferol 3-Methyl Ether | Isokaempferide|1592-70-7|3-Methoxyapigenin|3-Methylkaempferol|4-Vinylbenzylchloride|3-O-Methylkaempferol|Kaempferol 3-methyl ether|kaempferol-3-O-methyl ether|5,7-dihydroxy-2-(4-hydroxyphenyl)-3-methoxychromen-4-one|5,7,4'-trihydroxy-3-methoxyflavone|CHEBI:1579|CHEMBL165064|4H-1-BENZOPYRAN-4-ONE, 5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-3-METHOXY-|3-Methylkempferol|MLS000877008|3-MK|MEGxp0_000171|SCHEMBL1628023|SCHEMBL4637442|ACon1_001687|cid_5280862|DTXSID9Show More

Canonical SMILES:  COc1c(-c2ccc(O)cc2)oc2cc(O)cc(O)c2c1=O

Standard InChI:  InChI=1S/C16H12O6/c1-21-16-14(20)13-11(19)6-10(18)7-12(13)22-15(16)8-2-4-9(17)5-3-8/h2-7,17-19H,1H3

Standard InChI Key:  VJJZJBUCDWKPLC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -3.9072    2.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9091    1.5019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6321   -1.3486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    2.6973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2928    2.6973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9086   -1.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9097   -3.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2093   -3.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5078   -3.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5474   -3.6002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5067   -1.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2071   -0.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13  6  1  0
 13 14  1  0
 14  3  1  0
 14 15  2  0
  4 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 16  1  0
M  END

Alternative Forms

  1. Parent:

Associated Targets(Human)

CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RECQL Tbio ATP-dependent DNA helicase Q1 (5575 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BCL2L1 Tchem Apoptosis regulator Bcl-X (2604 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCL1 Tchem Induced myeloid leukemia cell differentiation protein Mcl-1 (3820 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
POLB Tchem DNA polymerase beta (23632 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KDM4A Tchem Lysine-specific demethylase 4A (52245 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BAZ2B Tchem Bromodomain adjacent to zinc finger domain protein 2B (56204 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ATAD5 Tbio ATPase family AAA domain-containing protein 5 (122566 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FEN1 Tchem Flap endonuclease 1 (12055 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
POLI Tchem DNA polymerase iota (116820 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
POLH Tchem DNA polymerase eta (21678 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
POLK Tbio DNA polymerase kappa (8653 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
WRN Tbio Werner syndrome ATP-dependent helicase (8824 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NFE2L2 Tchem Nuclear factor erythroid 2-related factor 2 (95332 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KB (17409 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Lu1 (576 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HepG2 (196354 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Enterovirus C (520 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vero (26788 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Dyrk1a Dual specificity tyrosine-phosphorylation-regulated kinase 1A (1629 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
fabI Enoyl-acyl-carrier protein reductase (415 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Phosphoglycerate kinase, glycosomal (2184 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
3T3-L1 (3664 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Spodoptera littoralis (798 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Artemia salina (1320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PGKC Phosphoglycerate kinase (480 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
L6 (7924 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
B16 (5829 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania amazonensis (3813 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma brucei gambiense (523 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Methionyl-tRNA synthetase, putative (70331 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
XDH Xanthine dehydrogenase (2296 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium berghei (192651 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
coaBC Coenzyme A biosynthesis bifunctional protein CoaBC (68296 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma cruzi (99888 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma brucei (78846 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
pks13 Polyketide synthase Pks13 (67344 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania donovani (89745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Histidine--tRNA ligase (69951 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Wolbachia pipientis (48835 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
clpP1 ClpP1P2 (69291 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mycobacterium tuberculosis (203094 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Histidine--tRNA ligase (68896 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Lysine--tRNA ligase (69390 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
trpS Tryptophan--tRNA ligase (65646 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 300.27Molecular Weight (Monoisotopic): 300.0634AlogP: 2.59#Rotatable Bonds: 2
Polar Surface Area: 100.13Molecular Species: ACIDHBA: 6HBD: 3
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 3#RO5 Violations (Lipinski):
CX Acidic pKa: 6.38CX Basic pKa: CX LogP: 2.57CX LogD: 1.42
Aromatic Rings: 3Heavy Atoms: 22QED Weighted: 0.67Np Likeness Score: 1.45

References

1. De Meyer N, Haemers A, Mishra L, Pandey HK, Pieters LA, Vanden Berghe DA, Vlietinck AJ..  (1991)  4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity.,  34  (2): [PMID:1847431] [10.1021/jm00106a039]
2. Usia T, Iwata H, Hiratsuka A, Watabe T, Kadota S, Tezuka Y..  (2004)  Sesquiterpenes and flavonol glycosides from Zingiber aromaticum and their CYP3A4 and CYP2D6 inhibitory activities.,  67  (7): [PMID:15270556] [10.1021/np030556a]
3. PubChem BioAssay data set, 
4. Muhammad A, Anis I, Ali Z, Awadelkarim S, Khan A, Khalid A, Shah MR, Galal M, Khan IA, Iqbal Choudhary M..  (2012)  Methylenebissantin: a rare methylene-bridged bisflavonoid from Dodonaea viscosa which inhibits Plasmodium falciparum enoyl-ACP reductase.,  22  (1): [PMID:22082562] [10.1016/j.bmcl.2011.10.072]
5. Zhang LB, Ji J, Lei C, Wang HY, Zhao QS, Hou AJ..  (2012)  Isoprenylated flavonoid and adipogenesis-promoting constituents of Dodonaea viscosa.,  75  (4): [PMID:22512738] [10.1021/np2009797]
6. Faini F, Labbe C, Coll J.  (1999)  Seasonal changes in chemical composition of epicuticular waxes from the leaves of Baccharis linearis,  27  (7): [10.1016/S0305-1978(98)00131-8]
7. Mai LH, Chabot GG, Grellier P, Quentin L, Dumontet V, Poulain C, Espindola LS, Michel S, Vo HT, Deguin B, Grougnet R..  (2015)  Antivascular and anti-parasite activities of natural and hemisynthetic flavonoids from New Caledonian Gardenia species (Rubiaceae).,  93  [PMID:25659770] [10.1016/j.ejmech.2015.01.012]
8. University of Dundee Gates Library Compound Collection,  [10.6019/CHEMBL3436366]
9. University of Dundee, Gates Library screen for HepG2 cell viability.,  [10.6019/CHEMBL3507680]
10. University of Dundee.  (2021)  University of Dundee, Small-Polar-MMV Screening Library,  [10.6019/CHEMBL3988442]
11. Nguyen TT, Truong BN, Doan Thi Mai H, Litaudon M, Nguyen VH, Do Thi T, Chau VM, Pham VC..  (2017)  Cytotoxic dammarane-type triterpenoids from the leaves of Viburnum sambucinum.,  27  (8): [PMID:28318944] [10.1016/j.bmcl.2017.03.014]
12. Santi MD, Paulino Zunini M, Vera B, Bouzidi C, Dumontet V, Abin-Carriquiry A, Grougnet R, Ortega MG..  (2018)  Xanthine oxidase inhibitory activity of natural and hemisynthetic flavonoids from Gardenia oudiepe (Rubiaceae) in vitro and molecular docking studies.,  143  [PMID:29207340] [10.1016/j.ejmech.2017.11.071]
13. Abraham, Matthew et al.  (2020)  Probing the Open Global Health Chemical Diversity Library for Multistage-Active Starting Points for Next-Generation Antimalarials,  (4): [PMID:32078764] [10.1021/acsinfecdis.9b00482]