(E)-7,8-Dimethoxy-3-(4'-methylthiobenzylidene)-4-chromanone

ID: ALA4531505

PubChem CID: 155546541

Max Phase: Preclinical

Molecular Formula: C19H18O4S

Molecular Weight: 342.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1OC)OC/C(=C\c1ccc(SC)cc1)C2=O

Standard InChI:  InChI=1S/C19H18O4S/c1-21-16-9-8-15-17(20)13(11-23-18(15)19(16)22-2)10-12-4-6-14(24-3)7-5-12/h4-10H,11H2,1-3H3/b13-10+

Standard InChI Key:  PZDIPKVFLNLSTG-JLHYYAGUSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   26.0091  -23.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1490  -22.3670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1478  -23.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8626  -23.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8608  -21.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5762  -22.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5750  -23.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2879  -23.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0079  -22.3653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2903  -21.9478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2856  -24.4298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4344  -21.9546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7221  -23.6116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4380  -23.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1495  -23.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8650  -23.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8683  -22.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1502  -21.9690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4377  -22.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4342  -21.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8583  -21.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5716  -20.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5837  -21.9728    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.2972  -22.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  6 10  1  0
  7  8  1  0
  8  1  1  0
  1  9  1  0
  9 10  1  0
  8 11  2  0
  2 12  1  0
  1 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 12 20  1  0
  5 21  1  0
 21 22  1  0
 17 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4531505

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 342.42

Molecular Weight (Monoisotopic): 342.0926

AlogP: 4.08

#Rotatable Bonds: 4

Polar Surface Area: 44.76

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.68

CX LogD: 3.68

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.62

Np Likeness Score: 0.05

References

1. Schwikkard S, Whitmore H, Sishtla K, Sulaiman RS, Shetty T, Basavarajappa HD, Waller C, Alqahtani A, Frankemoelle L, Chapman A, Crouch N, Wetschnig W, Knirsch W, Andriantiana J, Mas-Claret E, Langat MK, Mulholland D, Corson TW..  (2019)  The Antiangiogenic Activity of Naturally Occurring and Synthetic Homoisoflavonoids from the Hyacinthaceae ( sensu APGII).,  82  (5): [PMID:30951308] [10.1021/acs.jnatprod.8b00989]

Source

Source(1):

• Scientific Literature