1,7-dihydroxy-3,4-dimethoxy-9H-xanthen-9-one

ID: ALA4100829

Cas Number: 76907-77-2

PubChem CID: 5490798

Max Phase: Preclinical

Molecular Formula: C15H12O6

Molecular Weight: 288.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(O)c2c(=O)c3cc(O)ccc3oc2c1OC

Standard InChI:  InChI=1S/C15H12O6/c1-19-11-6-9(17)12-13(18)8-5-7(16)3-4-10(8)21-15(12)14(11)20-2/h3-6,16-17H,1-2H3

Standard InChI Key:  NQNPLVZPJSLIIA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   11.0348   -2.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0336   -3.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7417   -4.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7399   -2.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4485   -2.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4519   -3.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1643   -4.1180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1575   -2.4676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8745   -2.8796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8773   -3.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5919   -4.1126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3042   -3.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2974   -2.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5822   -2.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1530   -1.6505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3270   -2.4806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5758   -1.6475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5957   -4.9298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8899   -5.3416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0145   -4.1011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0198   -4.9183    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  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
  1 16  1  0
 14 17  1  0
 11 18  1  0
 18 19  1  0
 12 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4100829

   1,7-Dihydroxy-3,4-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: 288.25

Molecular Weight (Monoisotopic): 288.0634

AlogP: 2.37

#Rotatable Bonds: 2

Polar Surface Area: 89.13

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.64

CX Basic pKa: ┄

CX LogP: 2.69

CX LogD: 2.66

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.70

Np Likeness Score: 1.40

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]

2. Santos CMM, Freitas M, Fernandes E..  (2018)  A comprehensive review on xanthone derivatives as α-glucosidase inhibitors.,  157  [PMID:30282319] [10.1016/j.ejmech.2018.07.073]

Source

Source(1):

• Scientific Literature