5-Hydroxy-2-(4-hydroxy-phenyl)-3,7-dimethoxy-chromen-4-one

ID: ALA349724

Cas Number: 3301-49-3

PubChem CID: 5318869

Product Number: K648394, Order Now?

Max Phase: Preclinical

Molecular Formula: C17H14O6

Molecular Weight: 314.29

Molecule Type: Small molecule

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Associated Items:

Names and Identifiers

Synonyms: Kumatakenin | Kumatakenin|3301-49-3|Jaranol|Kumatakillin|5,4'-dihydroxy-3,7-dimethoxyflavone|Kaempferol 3,7-dimethyl ether|3,7-Di-O-methyl kaempferol|5-hydroxy-2-(4-hydroxyphenyl)-3,7-dimethoxychromen-4-one|UNII-5FAQ11412T|KAMATAKENIN|KUMATAKENIN A|Flavone, 4',5-dihydroxy-3,7-dimethoxy-|4H-1-Benzopyran-4-one, 5-hydroxy-2-(4-hydroxyphenyl)-3,7-dimethoxy-|5FAQ11412T|4',5-Dihydroxy-3,7-dimethoxyflavone|3,7-DIMETHYLKAEMPFEROL|DTXSID90186645|KAEMPFEROL 3,7-O-DIMETHYL ETHER|5-Hydroxy-2-(4-hydroxyphenyShow More

Canonical SMILES:  COc1cc(O)c2c(=O)c(OC)c(-c3ccc(O)cc3)oc2c1

Standard InChI:  InChI=1S/C17H14O6/c1-21-11-7-12(19)14-13(8-11)23-16(17(22-2)15(14)20)9-3-5-10(18)6-4-9/h3-8,18-19H,1-2H3

Standard InChI Key:  BJBUTJQYZDYRMJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    3.8754   -9.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743   -9.9631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5887  -10.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3019   -9.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3053   -9.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0241  -10.3763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7440   -9.9593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7405   -9.1267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0172   -8.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0127   -7.8866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599  -10.3748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4462   -9.9620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4592  -10.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4576  -11.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1719  -11.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8859  -11.1905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8809  -10.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1660   -9.9552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4526   -8.7162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4500   -7.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5973  -11.5992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5869   -8.7238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5869   -7.8988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  9 10  2  0
  2 11  1  0
  2  3  1  0
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  3  5  2  0
  7 13  1  0
  1  2  2  0
 13 14  2  0
  4 22  2  0
 14 15  1  0
 22  1  1  0
 15 16  2  0
  4  9  1  0
 16 17  1  0
  5  6  1  0
 17 18  2  0
 18 13  1  0
  6  7  1  0
  7  8  2  0
 19 20  1  0
  8 19  1  0
  8  9  1  0
 16 21  1  0
 22 23  1  0
M  END

Alternative Forms

  1. Parent:

    ALA349724

    Kumatakenin

Associated Targets(Human)

HeLa (62764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTPN1 Tchem Protein-tyrosine phosphatase 1B (8528 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HepG2 (196354 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
Human rhinovirus sp. (1587 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
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma brucei gambiense (523 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: 314.29Molecular Weight (Monoisotopic): 314.0790AlogP: 2.89#Rotatable Bonds: 3
Polar Surface Area: 89.13Molecular Species: NEUTRALHBA: 6HBD: 2
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 7.14CX Basic pKa: CX LogP: 2.72CX LogD: 2.26
Aromatic Rings: 3Heavy Atoms: 23QED Weighted: 0.77Np Likeness Score: 1.23

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. Chen JJ, Cho JY, Hwang TL, Chen IS..  (2008)  Benzoic acid derivatives, acetophenones, and anti-inflammatory constituents from Melicope semecarpifolia.,  71  (1): [PMID:18163582] [10.1021/np0704349]
3. Ryu YB, Kim JH, Park SJ, Chang JS, Rho MC, Bae KH, Park KH, Lee WS..  (2010)  Inhibition of neuraminidase activity by polyphenol compounds isolated from the roots of Glycyrrhiza uralensis.,  20  (3): [PMID:20064716] [10.1016/j.bmcl.2009.12.106]
4. 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]
5. Taleghani A, Emami SA, Tayarani-Najaran Z..  (2020)  Artemisia: a promising plant for the treatment of cancer.,  28  (1): [PMID:31784199] [10.1016/j.bmc.2019.115180]
6. Fan JR, Kuang Y, Dong ZY, Yi Y, Zhou YX, Li B, Qiao X, Ye M..  (2020)  Prenylated Phenolic Compounds from the Aerial Parts of Glycyrrhiza uralensis as PTP1B and α-Glucosidase Inhibitors.,  83  (4): [PMID:32196343] [10.1021/acs.jnatprod.9b00262]

Source