1,5-dihydroxy-7-methoxy-3-methylanthraquinone

ID: ALA472221

Cas Number: 148918-78-9

PubChem CID: 15138599

Max Phase: Preclinical

Molecular Formula: C16H12O5

Molecular Weight: 284.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(O)c2c(c1)C(=O)c1c(O)cc(C)cc1C2=O

Standard InChI:  InChI=1S/C16H12O5/c1-7-3-9-13(11(17)4-7)16(20)10-5-8(21-2)6-12(18)14(10)15(9)19/h3-6,17-18H,1-2H3

Standard InChI Key:  LLZYZGMVXFGQAY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   -1.7862   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  8 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  5 16  1  0
  1 16  2  0
  3 17  1  0
 18 19  1  0
 11 18  1  0
  9 20  1  0
  1 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA472221

   1,5-Dihydroxy-3-methoxy-7-methylanthracene-9,10-dione

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: 284.27

Molecular Weight (Monoisotopic): 284.0685

AlogP: 2.19

#Rotatable Bonds: 1

Polar Surface Area: 83.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.91

CX Basic pKa: ┄

CX LogP: 3.97

CX LogD: 3.85

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.72

Np Likeness Score: 0.81

References

1. Diaz F, Chai HB, Mi Q, Su BN, Vigo JS, Graham JG, Cabieses F, Farnsworth NR, Cordell GA, Pezzuto JM, Swanson SM, Kinghorn AD..  (2004)  Anthrone and oxanthrone C-glycosides from Picramnia latifolia collected in Peru.,  67  (3): [PMID:15043409] [10.1021/np030479j]

Source

Source(1):

• Scientific Literature