(5Z)-3-Benzyl-5-[3-(N,N-dimethylamino)benzylidene]furan-2(5H)-one

ID: ALA2228184

PubChem CID: 24861993

Max Phase: Preclinical

Molecular Formula: C20H19NO2

Molecular Weight: 305.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1cccc(/C=C2/C=C(Cc3ccccc3)C(=O)O2)c1

Standard InChI:  InChI=1S/C20H19NO2/c1-21(2)18-10-6-9-16(12-18)13-19-14-17(20(22)23-19)11-15-7-4-3-5-8-15/h3-10,12-14H,11H2,1-2H3/b19-13-

Standard InChI Key:  KONDROUPQMZSFW-UYRXBGFRSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   26.7486  -21.0177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0864  -21.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4267  -21.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6823  -20.2385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4972  -20.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0853  -22.3143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2082  -19.8339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9153  -20.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6226  -19.8358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3297  -20.2484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3258  -21.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6190  -21.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9119  -21.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7213  -21.4247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0127  -21.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3073  -21.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5966  -21.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5914  -20.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2969  -19.7981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0075  -20.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0361  -19.8405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7438  -20.2490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0360  -19.0233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  1  5  1  0
  2  6  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  8 13  2  0
  5  7  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 15 20  2  0
  3 14  1  0
 10 21  1  0
 21 22  1  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2228184

   (5Z)-3-benzyl-5-[[3-(dimethylamino)phenyl]methylidene]furan-2-one

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: 305.38

Molecular Weight (Monoisotopic): 305.1416

AlogP: 3.82

#Rotatable Bonds: 4

Polar Surface Area: 29.54

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.63

CX LogP: 4.44

CX LogD: 4.44

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.80

Np Likeness Score: 0.28

References

1. Teixeira RR, Barbosa LC, Forlani G, Piló-Veloso D, Walkimar de Mesquita Carneiro J..  (2008)  Synthesis of photosynthesis-inhibiting nostoclide analogues.,  56  (7): [PMID:18338868] [10.1021/jf072964g]

2. Teixeira RR, Pinheiro PF, Barbosa LC, Carneiro JW, Forlani G..  (2010)  QSAR modeling of photosynthesis-inhibiting nostoclide derivatives.,  66  (2): [PMID:19798697] [10.1002/ps.1855]

Source

Source(1):

• Scientific Literature