2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-3,6-bis((E)-3-methylbut-1-enyl)-4H-chromen-4-one

ID: ALA4249418

PubChem CID: 145983143

Max Phase: Preclinical

Molecular Formula: C25H26O6

Molecular Weight: 422.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)/C=C/c1c(O)cc2oc(-c3ccc(O)cc3O)c(/C=C/C(C)C)c(=O)c2c1O

Standard InChI:  InChI=1S/C25H26O6/c1-13(2)5-8-16-20(28)12-21-22(23(16)29)24(30)18(9-6-14(3)4)25(31-21)17-10-7-15(26)11-19(17)27/h5-14,26-29H,1-4H3/b8-5+,9-6+

Standard InChI Key:  MPIICGZAWWYYCZ-XVYDYJIPSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   10.7706   -2.5176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7695   -3.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4775   -3.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4758   -2.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1844   -2.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1878   -3.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9001   -3.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6137   -3.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6103   -2.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8934   -2.0962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3157   -2.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0250   -2.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7309   -2.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7288   -1.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0149   -0.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3119   -1.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0267   -3.3230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4347   -0.8659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9024   -4.5638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4761   -4.5633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0628   -2.1091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3225   -3.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3247   -4.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0336   -4.9638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0358   -5.7810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7402   -4.5533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0615   -3.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3541   -3.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6461   -3.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9387   -3.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6454   -4.5612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  9 11  1  0
 12 17  1  0
 14 18  1  0
  7 19  2  0
  3 20  1  0
  1 21  1  0
  8 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
  2 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4249418

   ---

Molecule Features

Natural Product: No

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: 422.48

Molecular Weight (Monoisotopic): 422.1729

AlogP: 5.62

#Rotatable Bonds: 5

Polar Surface Area: 111.13

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.47

CX Basic pKa: ┄

CX LogP: 5.91

CX LogD: 4.79

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.42

Np Likeness Score: 1.42

References

1. Li YR, Li GH, Zhou MX, Xiang L, Ren DM, Lou HX, Wang XN, Shen T..  (2018)  Discovery of natural flavonoids as activators of Nrf2-mediated defense system: Structure-activity relationship and inhibition of intracellular oxidative insults.,  26  (18): [PMID:30227999] [10.1016/j.bmc.2018.09.010]

Source

Source(1):

• Scientific Literature