(E)-3-(3,4-Dimethoxylphenyl)-1-(4-ethoxy-2-hydroxy-3-methyl-phenyl)prop-2-en-1-one

ID: ALA4535415

PubChem CID: 155547922

Max Phase: Preclinical

Molecular Formula: C20H22O5

Molecular Weight: 342.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOc1ccc(C(=O)/C=C/c2ccc(OC)c(OC)c2)c(O)c1C

Standard InChI:  InChI=1S/C20H22O5/c1-5-25-17-11-8-15(20(22)13(17)2)16(21)9-6-14-7-10-18(23-3)19(12-14)24-4/h6-12,22H,5H2,1-4H3/b9-6+

Standard InChI Key:  MYMDIYRCTBGOIW-RMKNXTFCSA-N

Molfile:  

 
     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   14.5165  -12.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8011  -12.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0857  -12.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5165  -11.4201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2321  -12.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9475  -12.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6588  -12.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6588  -13.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9475  -13.8965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2321  -13.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3742  -12.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9475  -11.4201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3742  -13.8965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3742  -14.7220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0897  -15.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3702  -12.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3702  -13.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6548  -13.8965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9435  -13.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9435  -12.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6548  -12.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2279  -13.8965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5125  -13.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6548  -14.7220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9435  -15.1327    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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  5 10  2  0
  7 11  1  0
  6 12  1  0
 14 15  1  0
 13 14  1  0
  8 13  1  0
  1  5  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 16 21  2  0
 22 23  1  0
 19 22  1  0
 24 25  1  0
 18 24  1  0
  3 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4535415

   ---

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: 342.39

Molecular Weight (Monoisotopic): 342.1467

AlogP: 4.01

#Rotatable Bonds: 7

Polar Surface Area: 64.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.54

CX Basic pKa: ┄

CX LogP: 4.63

CX LogD: 4.40

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.61

Np Likeness Score: 0.17

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