2-hydroxy-1,7-dimethoxy-9H-xanthen-9-one

ID: ALA4102665

PubChem CID: 12133312

Max Phase: Preclinical

Molecular Formula: C15H12O5

Molecular Weight: 272.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2oc3ccc(O)c(OC)c3c(=O)c2c1

Standard InChI:  InChI=1S/C15H12O5/c1-18-8-3-5-11-9(7-8)14(17)13-12(20-11)6-4-10(16)15(13)19-2/h3-7,16H,1-2H3

Standard InChI Key:  PIGYJVNDGBCMES-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   20.4655   -9.0716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4644   -9.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1724  -10.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1706   -8.6627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8792   -9.0680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8826   -9.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5950  -10.3006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5882   -8.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3052   -9.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3080   -9.8870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0227  -10.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7349   -9.8796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7281   -9.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0129   -8.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5837   -7.8330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0065   -7.8300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7110   -7.4159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7577   -8.6632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7575   -7.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4322   -8.6370    0.0000 O   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  8  1  0
  6  7  1  0
  7 10  1  0
  9  8  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  8 15  2  0
 14 16  1  0
 16 17  1  0
  1 18  1  0
 18 19  1  0
 13 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4102665

   2-Hydroxy-1,7-dimethoxyxanthone

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: 272.26

Molecular Weight (Monoisotopic): 272.0685

AlogP: 2.67

#Rotatable Bonds: 2

Polar Surface Area: 68.90

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.67

CX Basic pKa: ┄

CX LogP: 2.34

CX LogD: 2.34

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.73

Np Likeness Score: 1.00

References

1. Wang Q, Ma C, Ma Y, Li X, Chen Y, Chen J..  (2017)  Structure-activity relationships of diverse xanthones against multidrug resistant human tumor cells.,  27  (3): [PMID:28065566] [10.1016/j.bmcl.2016.12.045]

Source

Source(1):

• Scientific Literature