Dimethyl 3-methoxy-4,4'-oxyneolign-9,9'-dioate

ID: ALA2269137

PubChem CID: 11516262

Max Phase: Preclinical

Molecular Formula: C21H24O6

Molecular Weight: 372.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)CCc1ccc(Oc2ccc(CCC(=O)OC)cc2OC)cc1

Standard InChI:  InChI=1S/C21H24O6/c1-24-19-14-16(8-13-21(23)26-3)6-11-18(19)27-17-9-4-15(5-10-17)7-12-20(22)25-2/h4-6,9-11,14H,7-8,12-13H2,1-3H3

Standard InChI Key:  SYWGPADQOCSBBG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   29.1824   -1.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1812   -2.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8960   -3.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6125   -2.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6096   -1.9089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8942   -1.4997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3226   -1.4937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.0386   -1.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0384   -2.7261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7535   -3.1358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4674   -2.7206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4616   -1.8913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7459   -1.4854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4664   -3.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7522   -2.7388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0374   -3.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3228   -2.7398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0363   -3.9779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.1840   -3.1295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8964   -2.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6129   -3.1222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6198   -3.9468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.3279   -2.7057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8918   -0.6747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.6050   -0.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6090   -3.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9088   -4.3653    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
 17 26  1  0
 22 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2269137

   APTENIOL C

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: 372.42

Molecular Weight (Monoisotopic): 372.1573

AlogP: 3.70

#Rotatable Bonds: 9

Polar Surface Area: 71.06

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.77

CX LogD: 3.77

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.63

Np Likeness Score: -0.02

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