7,7'-dimethoxy-5'-(methoxycarbonyl)-4,4'-bibenzo[d][1,3]dioxole-5-carboxylic acid

ID: ALA4104403

Cas Number: 205117-47-1

PubChem CID: 12016591

Max Phase: Preclinical

Molecular Formula: C19H16O10

Molecular Weight: 404.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1cc(OC)c2c(c1-c1c(C(=O)O)cc(OC)c3c1OCO3)OCO2

Standard InChI:  InChI=1S/C19H16O10/c1-23-10-4-8(18(20)21)12(16-14(10)26-6-28-16)13-9(19(22)25-3)5-11(24-2)15-17(13)29-7-27-15/h4-5H,6-7H2,1-3H3,(H,20,21)

Standard InChI Key:  VVRXOUGWCMBBIS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   25.5587  -11.9584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5569  -13.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2738  -13.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2709  -12.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8420  -13.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8383  -12.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0509  -12.1156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5680  -12.7866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0570  -13.4532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5578  -14.4328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8438  -14.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5277  -10.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5339   -9.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8159   -9.4626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8167  -10.2855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2477   -9.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2451  -10.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0280  -10.5441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5144   -9.8789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0321   -9.2109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5351   -8.2227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2502   -7.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1023  -10.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3879  -10.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1022  -11.5228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3880   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9843  -11.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6997  -12.3647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9822  -11.1289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0
  5  2  2  0
  2  3  1  0
  3  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  2 10  1  0
 10 11  1  0
 12 17  2  0
 16 13  2  0
 13 14  1  0
 14 15  2  0
 15 12  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 16  1  0
 13 21  1  0
 21 22  1  0
  1 12  1  0
 15 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  1  0
  4 27  1  0
 27 28  1  0
 27 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4104403

   7-Methoxy-4-(7-methoxy-5-methoxycarbonyl-1,3-benzodioxol-4-yl)-1,3-benzodioxole-5-carboxylic acid

Molecule Features

Natural Product: No

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: 404.33

Molecular Weight (Monoisotopic): 404.0743

AlogP: 2.31

#Rotatable Bonds: 5

Polar Surface Area: 118.98

Molecular Species: ACID

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.40

CX Basic pKa: ┄

CX LogP: 2.21

CX LogD: -1.19

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.74

Np Likeness Score: 0.54

References

1. Gu X, Huang Z, Ren Z, Tang X, Xue R, Luo X, Peng S, Peng H, Lu B, Tian J, Zhang Y..  (2017)  Potent Inhibition of Nitric Oxide-Releasing Bifendate Derivatives against Drug-Resistant K562/A02 Cells in Vitro and in Vivo.,  60  (3): [PMID:28068095] [10.1021/acs.jmedchem.6b01075]

Source

Source(1):

• Scientific Literature