(+/-)-Dihydroquercetin

ID: ALA337309

Max Phase: Preclinical

Molecular Formula: C15H12O7

Molecular Weight: 304.25

Molecule Type: Small molecule

Names and Identifiers

Synonyms: NSC-2801

Canonical SMILES:  O=C1c2c(O)cc(O)cc2OC(c2ccc(O)c(O)c2)C1O

Standard InChI:  InChI=1S/C15H12O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,14-19,21H

Standard InChI Key:  CXQWRCVTCMQVQX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -5.2009  -12.2201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2021  -13.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4902  -13.4588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4921  -11.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7750  -12.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7712  -13.0485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0525  -13.4592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3329  -13.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3365  -12.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0599  -11.7943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0500  -14.2830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6260  -11.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9108  -12.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1994  -11.7939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2017  -10.9692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9216  -10.5599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6302  -10.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9146  -11.8087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4927  -14.2826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9273   -9.7361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5098  -10.5538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6181  -13.4518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
  7 11  2  0
  2  3  1  0
 12 13  2  0
  3  6  2  0
 13 14  1  0
  1  2  2  0
 14 15  2  0
  5  4  2  0
 15 16  1  0
  4  1  1  0
 16 17  2  0
 17 12  1  0
  9 12  1  0
  5 10  1  0
  1 18  1  0
  6  7  1  0
  3 19  1  0
  7  8  1  0
 16 20  1  0
  8  9  1  0
 15 21  1  0
  9 10  1  0
  8 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA337309

   TAXIFOLIN

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: 304.25

Molecular Weight (Monoisotopic): 304.0583

AlogP: 1.19

#Rotatable Bonds: 1

Polar Surface Area: 127.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.74

CX Basic pKa: ┄

CX LogP: 1.82

CX LogD: 1.65

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.50

Np Likeness Score: 2.30

References

1. Ji XD, Melman N, Jacobson KA..  (1996)  Interactions of flavonoids and other phytochemicals with adenosine receptors.,  39  (3): [PMID:8576921] [10.1021/jm950661k]

2. Costa SM, Lemos TL, Pessoa OD, Pessoa C, Montenegro RC, Braz-Filho R..  (2001)  Chemical constituents from Lippia sidoides and cytotoxic activity.,  64  (6): [PMID:11421746] [10.1021/np0005917]

3. Cos P, Ying L, Calomme M, Hu JP, Cimanga K, Van Poel B, Pieters L, Vlietinck AJ, Vanden Berghe D..  (1998)  Structure-activity relationship and classification of flavonoids as inhibitors of xanthine oxidase and superoxide scavengers.,  61  (1): [PMID:9461655] [10.1021/np970237h]

4. Edwards JM, Raffauf RF, Le Quesne PW..  (1979)  Antineoplastic activity and cytotoxicity of flavones, isoflavones, and flavanones.,  42  (1): [PMID:469554] [10.1021/np50001a002]

5. Chu SC, Hsieh YS, Lin JY..  (1992)  Inhibitory effects of flavonoids on Moloney murine leukemia virus reverse transcriptase activity.,  55  (2): [PMID:1378087] [10.1021/np50080a005]

6. Lee S, Woo Y, Shin SY, Lee YH, Lim Y..  (2009)  Relationships between the structures of flavanone derivatives and their effects in enhancing early growth response-1 gene expression.,  19  (8): [PMID:19307119] [10.1016/j.bmcl.2009.03.017]

7. Diamandis P, Wildenhain J, Clarke ID, Sacher AG, Graham J, Bellows DS, Ling EK, Ward RJ, Jamieson LG, Tyers M, Dirks PB..  (2007)  Chemical genetics reveals a complex functional ground state of neural stem cells.,  3  (5): [PMID:17417631] [10.1038/nchembio873]

8. Yuan J, Johnson RL, Huang R, Wichterman J, Jiang H, Hayton K, Fidock DA, Wellems TE, Inglese J, Austin CP, Su XZ..  (2009)  Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.,  5  (10): [PMID:19734910] [10.1038/nchembio.215]

9. Kuhn I, Kellenberger E, Said-Hassane F, Villa P, Rognan D, Lobstein A, Haiech J, Hibert M, Schuber F, Muller-Steffner H..  (2010)  Identification by high-throughput screening of inhibitors of Schistosoma mansoni NAD(+) catabolizing enzyme.,  18  (22): [PMID:20951593] [10.1016/j.bmc.2010.09.041]

10. PubChem BioAssay data set, 

11. PubChem BioAssay data set, 

12. PubChem BioAssay data set, 

13. PubChem BioAssay data set, 

14. Kellenberger E, Kuhn I, Schuber F, Muller-Steffner H..  (2011)  Flavonoids as inhibitors of human CD38.,  21  (13): [PMID:21641214] [10.1016/j.bmcl.2011.05.022]

15. PubChem BioAssay data set, 

16. PubChem BioAssay data set, 

17. Krimm I, Lancelin JM, Praly JP..  (2012)  Binding evaluation of fragment-based scaffolds for probing allosteric enzymes.,  55  (3): [PMID:22229710] [10.1021/jm201439b]

18. Bais HP, Walker TS, Kennan AJ, Stermitz FR, Vivanco JM..  (2003)  Structure-dependent phytotoxicity of catechins and other flavonoids: flavonoid conversions by cell-free protein extracts of Centaurea maculosa (spotted knapweed) roots.,  51  (4): [PMID:12568546] [10.1021/jf020978a]

19. Xiao ZP, Peng ZY, Dong JJ, He J, Ouyang H, Feng YT, Lu CL, Lin WQ, Wang JX, Xiang YP, Zhu HL..  (2013)  Synthesis, structure-activity relationship analysis and kinetics study of reductive derivatives of flavonoids as Helicobacter pylori urease inhibitors.,  63  [PMID:23567958] [10.1016/j.ejmech.2013.03.016]

20. Wang L, Zhang S, Zhu J, Zhu L, Liu X, Shan L, Huang J, Zhang W, Li H..  (2014)  Identification of diverse natural products as falcipain-2 inhibitors through structure-based virtual screening.,  24  (5): [PMID:24530004] [10.1016/j.bmcl.2014.01.074]

21. PubChem BioAssay data set, 

22. Jacques SA, Kuhn I, Koniev O, Schuber F, Lund FE, Wagner A, Muller-Steffner H, Kellenberger E..  (2015)  Discovery of Potent Inhibitors of Schistosoma mansoni NAD⁺ Catabolizing Enzyme.,  58  (8): [PMID:25803425] [10.1021/acs.jmedchem.5b00203]

23. Beck S, Muellers SN, Benzie AL, Parkin DW, Stockman BJ..  (2015)  Adenosine/guanosine preferring nucleoside ribohydrolase is a distinct, druggable antitrichomonal target.,  25  (22): [PMID:26592812] [10.1016/j.bmcl.2015.10.030]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays