2-(benzo[d][1,3]dioxol-5-ylmethyl)succinic acid

ID: ALA1684097

Cas Number: 57420-27-6

PubChem CID: 284727

Max Phase: Preclinical

Molecular Formula: C12H12O6

Molecular Weight: 252.22

Molecule Type: Small molecule

Names and Identifiers

Synonyms: NSC-140905 | 57420-27-6|2-(1,3-benzodioxol-5-ylmethyl)butanedioic acid|NSC140905|2-(benzo[d][1,3]dioxol-5-ylmethyl)succinic acid|2-[(2H-1,3-benzodioxol-5-yl)methyl]butanedioic acid|NSC-140905|piperonylbutanedioic acid|CHEMBL1684097|SCHEMBL19018239|DTXSID70301071|AKOS022351964|AS-66895|NCI60_000898|2-(1,3-benzodioxol-5-ylmethyl)succinic acid|D94093

Canonical SMILES:  O=C(O)CC(Cc1ccc2c(c1)OCO2)C(=O)O

Standard InChI:  InChI=1S/C12H12O6/c13-11(14)5-8(12(15)16)3-7-1-2-9-10(4-7)18-6-17-9/h1-2,4,8H,3,5-6H2,(H,13,14)(H,15,16)

Standard InChI Key:  VXIGMHUBZXMCIU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
   -2.4667    1.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7522    1.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0377    1.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7522    2.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1811    1.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4667    0.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7522   -0.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7569   -1.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3305   -0.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0447    0.2120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3279   -1.0259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0443   -1.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8717   -2.2498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0484   -2.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2876   -1.5793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1811    2.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8956    2.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4667    2.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11  9  1  0
  1  5  1  0
  9 10  2  0
 10  7  1  0
 11 12  2  0
  2  3  1  0
  1  6  1  0
  1  2  1  0
  6  7  1  0
  2  4  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 11  1  0
  7  8  2  0
  5 16  1  0
  8 12  1  0
 16 17  1  0
 16 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1684097

   2-(1,3-Benzodioxol-5-ylmethyl)butanedioic 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: 252.22

Molecular Weight (Monoisotopic): 252.0634

AlogP: 1.13

#Rotatable Bonds: 5

Polar Surface Area: 93.06

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.58

CX Basic pKa: ┄

CX LogP: 1.35

CX LogD: -4.32

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.82

Np Likeness Score: 0.45

References

1. El-Hachem N, Nemer G..  (2011)  Identification of new GATA4-small molecule inhibitors by structure-based virtual screening.,  19  (5): [PMID:21310620] [10.1016/j.bmc.2011.01.022]

2. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays