Tournefolic acid B methyl ester

ID: ALA4102133

PubChem CID: 11558898

Max Phase: Preclinical

Molecular Formula: C18H14O6

Molecular Weight: 326.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)/C=C/c1ccc(O)c2c1C=Cc1cc(O)c(O)cc1O2

Standard InChI:  InChI=1S/C18H14O6/c1-23-17(22)7-4-10-3-6-13(19)18-12(10)5-2-11-8-14(20)15(21)9-16(11)24-18/h2-9,19-21H,1H3/b7-4+

Standard InChI Key:  JYFWREYLXRHORV-QPJJXVBHSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   12.7055   -6.4573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3002   -7.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4826   -7.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2893   -5.7487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5232   -6.4498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1107   -8.8824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9152   -8.6953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2721   -7.9635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9141   -7.2108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1073   -7.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4693   -7.5488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4689   -8.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0780   -7.8988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5399   -8.5818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1826   -9.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3704   -9.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7597   -8.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0508   -8.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0511   -7.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7604   -7.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3381   -7.1393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3374   -8.7820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0084  -10.1132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9252   -5.7383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  1  4  2  0
  1  5  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
  6 12  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
  7 16  2  0
  8 13  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 11 20  2  0
 12 17  2  0
 19 21  1  0
 18 22  1  0
 16 23  1  0
  3 13  1  0
  5 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4102133

   Tournefolic acid B Methyl ester

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: 326.30

Molecular Weight (Monoisotopic): 326.0790

AlogP: 3.27

#Rotatable Bonds: 2

Polar Surface Area: 96.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.27

CX Basic pKa: ┄

CX LogP: 3.47

CX LogD: 3.42

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.38

Np Likeness Score: 1.75

References

1. Chen PC, Tsai WJ, Ueng YF, Tzeng TT, Chen HL, Zhu PR, Huang CH, Shiao YJ, Li WT..  (2017)  Neuroprotective and Antineuroinflammatory Effects of Hydroxyl-Functionalized Stilbenes and 2-Arylbenzo[b]furans.,  60  (9): [PMID:28459572] [10.1021/acs.jmedchem.7b00376]

Source

Source(1):

• Scientific Literature