3-Methoxy-4,4'-oxyneolign-9,9'-dioic acid

ID: ALA2269136

PubChem CID: 11617133

Max Phase: Preclinical

Molecular Formula: C19H20O6

Molecular Weight: 344.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(CCC(=O)O)ccc1Oc1ccc(CCC(=O)O)cc1

Standard InChI:  InChI=1S/C19H20O6/c1-24-17-12-14(6-11-19(22)23)4-9-16(17)25-15-7-2-13(3-8-15)5-10-18(20)21/h2-4,7-9,12H,5-6,10-11H2,1H3,(H,20,21)(H,22,23)

Standard InChI Key:  SLWZVKXLJQIUKB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   16.5606   -1.9749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5594   -2.8022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2742   -3.2151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9907   -2.8017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9877   -1.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2724   -1.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7007   -1.5561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4167   -1.9658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4164   -2.7885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1316   -3.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8455   -2.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8396   -1.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1240   -1.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8446   -3.2141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1306   -2.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4157   -3.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7011   -2.8021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4146   -4.0402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5619   -3.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2744   -2.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9908   -3.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9977   -4.0091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7059   -2.7680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2700   -0.7372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9832   -0.3225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  2 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 11 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
  6 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2269136

   APTENIOL B

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: 344.36

Molecular Weight (Monoisotopic): 344.1260

AlogP: 3.52

#Rotatable Bonds: 9

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: 3.35

CX Basic pKa: ┄

CX LogP: 3.48

CX LogD: -3.17

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.72

Np Likeness Score: 0.07

References

1. DellaGreca M, Di Marino C, Previtera L, Purcaro R, Zarrelli A.  (2005)  Apteniols AF, oxyneolignans from the leaves of Aptenia cordifolia,  61  (50): [10.1016/j.tet.2005.09.054]

Source

Source(1):

• Scientific Literature