3,4-dihydro-3,5,8-trihydroxy-6-methoxy-2,2,7-trimethyl-2Hpyrano[2,3-a]acridin-12(7H)-one

ID: ALA1668602

Cas Number: 935521-56-5

PubChem CID: 53318269

Max Phase: Preclinical

Molecular Formula: C20H21NO6

Molecular Weight: 371.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(O)c2c(c3c(=O)c4cccc(O)c4n(C)c13)OC(C)(C)C(O)C2

Standard InChI:  InChI=1S/C20H21NO6/c1-20(2)12(23)8-10-17(25)19(26-4)15-13(18(10)27-20)16(24)9-6-5-7-11(22)14(9)21(15)3/h5-7,12,22-23,25H,8H2,1-4H3

Standard InChI Key:  QAUFACGSJSABOB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   16.4860  -12.6827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4860  -11.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7724  -12.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7750  -11.4479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0628  -11.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3475  -11.4459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3489  -12.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0618  -12.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1994  -11.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1977  -12.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9105  -12.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6253  -12.2716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0628  -13.5106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4871  -13.5098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3420  -12.6844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9098  -13.5105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6257  -13.9246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4845  -10.2015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9076  -10.2077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9058  -11.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6151  -11.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3305  -11.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3322  -10.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6185   -9.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1990   -9.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1977   -9.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0497   -9.7995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 20  9  1  0
  1 10  1  0
  8 13  1  0
  5  6  2  0
  1 14  1  0
  9  2  1  0
 12 15  1  0
  6  7  1  0
 11 16  1  0
 16 17  1  0
  7  8  2  0
  2 18  2  0
 19 20  1  0
  8  3  1  0
  4  2  1  0
  3  4  2  0
  9 10  2  0
  3  1  1  0
 10 11  1  0
 19 24  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
  4  5  1  0
 24 25  1  0
 11 12  2  0
 24 26  1  0
 12 21  1  0
 23 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1668602

   3,4-dihydro-3,5,8-trihydroxy-6-methoxy-2,2,7-trimethyl-2Hpyrano[2,3-a]acridin-12(7H)-one

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: 371.39

Molecular Weight (Monoisotopic): 371.1369

AlogP: 2.19

#Rotatable Bonds: 1

Polar Surface Area: 101.15

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.55

CX Basic pKa: ┄

CX LogP: 2.31

CX LogD: 2.28

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.57

Np Likeness Score: 2.22

References

1. Severino RP, Guido RV, Marques EF, Brömme D, da Silva MF, Fernandes JB, Andricopulo AD, Vieira PC..  (2011)  Acridone alkaloids as potent inhibitors of cathepsin V.,  19  (4): [PMID:21277783] [10.1016/j.bmc.2010.12.056]

Source

Source(1):

• Scientific Literature