1-hydroxy-3-methoxy-10-methyl-9-acridone

ID: ALA1094824

PubChem CID: 5377412

Max Phase: Preclinical

Molecular Formula: C15H13NO3

Molecular Weight: 255.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(O)c2c(=O)c3ccccc3n(C)c2c1

Standard InChI:  InChI=1S/C15H13NO3/c1-16-11-6-4-3-5-10(11)15(18)14-12(16)7-9(19-2)8-13(14)17/h3-8,17H,1-2H3

Standard InChI Key:  OCUBFJMZYYIVBO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   -3.8598   -4.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8610   -4.9133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1499   -5.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1517   -3.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4402   -4.0867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4367   -4.9154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7215   -5.3245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7283   -3.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0084   -4.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0055   -4.9092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2879   -5.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4273   -4.9017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4204   -4.0703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2977   -3.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7327   -2.8467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3042   -2.8436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1405   -5.3075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1458   -6.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7189   -6.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0
  4  1  1  0
  9 10  2  0
  5  6  1  0
 10 11  1  0
 11 12  2  0
  2  3  1  0
 12 13  1  0
  3  6  2  0
 13 14  2  0
 14  9  1  0
  1  2  2  0
  8 15  2  0
  5  8  1  0
 14 16  1  0
  6  7  1  0
 12 17  1  0
  7 10  1  0
 17 18  1  0
  9  8  1  0
  7 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1094824

   1-Hydroxy-3-methoxy-10-methylacridone

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: 255.27

Molecular Weight (Monoisotopic): 255.0895

AlogP: 2.41

#Rotatable Bonds: 1

Polar Surface Area: 51.46

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.84

CX Basic pKa: ┄

CX LogP: 3.31

CX LogD: 3.30

Aromatic Rings: 3

Heavy Atoms: 19

QED Weighted: 0.68

Np Likeness Score: 0.62

References

1. Ngoumfo RM, Jouda JB, Mouafo FT, Komguem J, Mbazoa CD, Shiao TC, Choudhary MI, Laatsch H, Legault J, Pichette A, Roy R..  (2010)  In vitro cytotoxic activity of isolated acridones alkaloids from Zanthoxylum leprieurii Guill. et Perr.,  18  (10): [PMID:20413315] [10.1016/j.bmc.2010.03.040]

2. Putic A, Stecher L, Prinz H, Müller K..  (2010)  Structure-activity relationship studies of acridones as potential antipsoriatic agents. 2. Synthesis and antiproliferative activity of 10-substituted hydroxy-10H-acridin-9-ones against human keratinocyte growth.,  45  (11): [PMID:20850910] [10.1016/j.ejmech.2010.08.059]

3. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays