5,7-Dihydroxy-3,6-dimethoxy-2-(4-methoxy-phenyl)-chromen-4-one

ID: ALA161957

Cas Number: 27782-63-4

PubChem CID: 5281695

Max Phase: Preclinical

Molecular Formula: C18H16O7

Molecular Weight: 344.32

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Santin | Santin|27782-63-4|5,7-Dihydroxy-3,6,4'-trimethoxyflavone|5,7-dihydroxy-3,6-dimethoxy-2-(4-methoxyphenyl)chromen-4-one|CHEBI:9024|CHEMBL161957|5,7-Dihydroxy-3,6-dimethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one|5785Y952EH|4H-1-Benzopyran-4-one, 5,7-dihydroxy-3,6-dimethoxy-2-(4-methoxyphenyl)-|CENTAURIDIN|3-METHYLBETULETOL|SCHEMBL82415|MLS000863609|MEGxp0_001724|UNII-5785Y952EH|DTXSID10182109|DWZAJFZEYZIHPO-UHFFFAOYSA-N|HMS2268N18|5,7-Dihydroxy-3,6-dimethoxy-2-(4-methoxy-phenyl)-chromenShow More⌵

Canonical SMILES:  COc1ccc(-c2oc3cc(O)c(OC)c(O)c3c(=O)c2OC)cc1

Standard InChI:  InChI=1S/C18H16O7/c1-22-10-6-4-9(5-7-10)16-18(24-3)15(21)13-12(25-16)8-11(19)17(23-2)14(13)20/h4-8,19-20H,1-3H3

Standard InChI Key:  DWZAJFZEYZIHPO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    0.1795    0.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1795   -0.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5353   -1.2099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5353   -2.0377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2500   -0.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9649   -1.2099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6838   -0.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6838    0.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9649    0.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2500    0.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5353    0.4418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8985    0.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8985    1.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6133    1.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3281    1.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3281    0.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6133    0.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0413    1.6820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0409    2.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3965    0.4430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9639   -2.0336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3965   -1.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1106   -0.8004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8928   -1.2102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8925   -2.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0
  9 10  1  0
  5 10  2  0
 10 11  1  0
  1 11  1  0
  1 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 17  2  0
 15 18  1  0
  1  2  2  0
 18 19  1  0
  2  3  1  0
  8 20  1  0
  3  4  2  0
  6 21  1  0
  3  5  1  0
  7 22  1  0
  5  6  1  0
 22 23  1  0
  6  7  2  0
  2 24  1  0
  7  8  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA161957

   SANTIN

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 344.32

Molecular Weight (Monoisotopic): 344.0896

AlogP: 2.90

#Rotatable Bonds: 4

Polar Surface Area: 98.36

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.91

CX Basic pKa: ┄

CX LogP: 2.56

CX LogD: 1.94

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.75

Np Likeness Score: 1.22

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. Martinez J, Silván AM, Abad MJ, Bermejo P, Villar A, Söllhuber M..  (1997)  Isolation of two flavonoids from Tanacetum microphyllum as PMA-induced ear edema inhibitors.,  60  (2): [PMID:9051913] [10.1021/np960163u]

3. Li H, Meng JC, Cheng CH, Higa T, Tanaka J, Tan RX..  (1999)  New guaianolides and xanthine oxidase inhibitory flavonols from ajania fruticulosa,  62  (7): [PMID:10425142] [10.1021/np990009i]

4. Aljancić I, Vajs V, Menković N, Karadzić I, Juranić N, Milosavljević S, Macura S..  (1999)  Flavones and sesquiterpene lactones from Achillea atrata subsp. multifida: antimicrobial activity.,  62  (6): [PMID:10395518] [10.1021/np980536m]

5. PubChem BioAssay data set, 

6. 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]

7. Muriuki B, Midiwo JO, Mbugua PM, Keriko JM.  (2013)  The antimycobacterial MICs, SARs, and QSARs of some ethnobotanically selected phytocompounds,  22  (11): [10.1007/s00044-013-0485-8]

8. 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]

9. 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]

10. Chibli LA, Schmidt TJ, Nonato MC, Calil FA, Da Costa FB..  (2018)  Natural products as inhibitors of Leishmania major dihydroorotate dehydrogenase.,  157  [PMID:30145372] [10.1016/j.ejmech.2018.08.033]

11. Shen CC, Wei WC, Lin LC..  (2019)  Diterpenoids and Bisnorditerpenoids from Blumea aromatica.,  82  (11): [PMID:31646857] [10.1021/acs.jnatprod.9b00674]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays