ID: ALA161957

Max Phase: Preclinical

Molecular Formula: C18H16O7

Molecular Weight: 344.32

Molecule Type: Small molecule

Representations

Synonyms (1): Santin
Synonyms from Alternative Forms(1):

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

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

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: 0

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

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