3,5,7-trihydroxy-2-(4-hydroxyphenyl)chroman-4-one

ID: ALA398847

Cas Number: 724434-08-6

PubChem CID: 662

Product Number: C693313, Order Now?

Max Phase: Preclinical

Molecular Formula: C15H12O6

Molecular Weight: 288.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1c2c(O)cc(O)cc2OC(c2ccc(O)cc2)C1O

Standard InChI:  InChI=1S/C15H12O6/c16-8-3-1-7(2-4-8)15-14(20)13(19)12-10(18)5-9(17)6-11(12)21-15/h1-6,14-18,20H

Standard InChI Key:  PADQINQHPQKXNL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    1.4986   -8.2166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4974   -9.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2122   -9.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2104   -7.8039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9258   -8.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9246   -9.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6376   -9.4544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3563   -9.0435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3574   -8.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6399   -7.7975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0710   -7.8072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7848   -8.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4998   -7.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5022   -6.9872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7837   -6.5731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0717   -6.9856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2171   -6.5755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0696   -9.4580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6353  -10.2794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7840   -7.8043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042  -10.2792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
  5  6  1  0
 11 12  2  0
  2  3  1  0
 12 13  1  0
  3  6  2  0
 13 14  2  0
  1  2  2  0
 14 15  1  0
  5  4  2  0
 15 16  2  0
 16 11  1  0
  9 11  1  0
  4  1  1  0
 14 17  1  0
  5 10  1  0
  8 18  1  0
  6  7  1  0
  7 19  2  0
  7  8  1  0
  1 20  1  0
  8  9  1  0
  3 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA398847

   Compound TCFN91628

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: 288.25

Molecular Weight (Monoisotopic): 288.0634

AlogP: 1.48

#Rotatable Bonds: 1

Polar Surface Area: 107.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.75

CX Basic pKa: ┄

CX LogP: 2.12

CX LogD: 1.96

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.63

Np Likeness Score: 2.16

References

1. Chen Y, Liu H, Xu S, Wang T, Li W.  (2015)  Targeting microsomal prostaglandin E2synthase-1 (mPGES-1): the development of inhibitors as an alternative to non-steroidal anti-inflammatory drugs (NSAIDs),  6  (12): [10.1039/C5MD00278H]

2. 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