(Z)-3-benzyl-5-(3-hydroxybenzylidene)furan-2(5H)-one

ID: ALA2228187

PubChem CID: 76311458

Max Phase: Preclinical

Molecular Formula: C18H14O3

Molecular Weight: 278.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1O/C(=C\c2cccc(O)c2)C=C1Cc1ccccc1

Standard InChI:  InChI=1S/C18H14O3/c19-16-8-4-7-14(10-16)11-17-12-15(18(20)21-17)9-13-5-2-1-3-6-13/h1-8,10-12,19H,9H2/b17-11-

Standard InChI Key:  LDJGPVSSANSPSQ-BOPFTXTBSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   12.4643  -24.3814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8021  -24.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1424  -24.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3980  -23.6022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2129  -23.6038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8010  -25.6780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9238  -23.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6309  -23.6102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3382  -23.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0453  -23.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0415  -24.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3346  -24.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6275  -24.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4369  -24.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7284  -24.3861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0229  -24.7985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3123  -24.3927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3071  -23.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0125  -23.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7232  -23.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7549  -23.2068    0.0000 O   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
M  END

Alternative Forms

1. Parent:

   

   ALA2228187

   (5Z)-3-benzyl-5-[(3-hydroxyphenyl)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: 278.31

Molecular Weight (Monoisotopic): 278.0943

AlogP: 3.46

#Rotatable Bonds: 3

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.34

CX Basic pKa: ┄

CX LogP: 4.03

CX LogD: 4.03

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.87

Np Likeness Score: 0.96

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