3,3',5-Trimethoxy-4,4'-oxyneolign-9,9'-dioic acid

ID: ALA2269138

PubChem CID: 11545888

Max Phase: Preclinical

Molecular Formula: C21H24O8

Molecular Weight: 404.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(CCC(=O)O)ccc1Oc1c(OC)cc(CCC(=O)O)cc1OC

Standard InChI:  InChI=1S/C21H24O8/c1-26-16-10-13(5-8-19(22)23)4-7-15(16)29-21-17(27-2)11-14(6-9-20(24)25)12-18(21)28-3/h4,7,10-12H,5-6,8-9H2,1-3H3,(H,22,23)(H,24,25)

Standard InChI Key:  YBOIZGBZDGKRLF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
    3.7902   -8.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7890   -9.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5039   -9.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2202   -9.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2174   -8.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5021   -7.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9304   -7.8018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6463   -8.2117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6460   -9.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3613   -9.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0751   -9.0287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0694   -8.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3536   -7.7936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0743   -9.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3601   -9.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6454   -9.4588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9307   -9.0479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6441  -10.2860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7917   -9.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5040   -9.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2206   -9.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2275  -10.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9356   -9.0139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4995   -6.9829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2128   -6.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9354   -9.4589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9367  -10.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6416   -9.8582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3538  -10.2746    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
  4 26  1  0
 26 27  1  0
  9 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2269138

   APTENIOL D

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: 404.42

Molecular Weight (Monoisotopic): 404.1471

AlogP: 3.54

#Rotatable Bonds: 11

Polar Surface Area: 111.52

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.12

CX Basic pKa: ┄

CX LogP: 3.17

CX LogD: -3.63

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.58

Np Likeness Score: 0.27

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