5-Iodomethylene-4-phenyl-dihydro-furan-2-one

ID: ALA75703

PubChem CID: 13553439

Max Phase: Preclinical

Molecular Formula: C11H9IO2

Molecular Weight: 300.10

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1CC(c2ccccc2)/C(=C\I)O1

Standard InChI:  InChI=1S/C11H9IO2/c12-7-10-9(6-11(13)14-10)8-4-2-1-3-5-8/h1-5,7,9H,6H2/b10-7+

Standard InChI Key:  BTNAULOGRAPUBV-JXMROGBWSA-N

Molfile:  

     RDKit          2D

 14 15  0  0  0  0  0  0  0  0999 V2000
    1.6500   -4.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042   -4.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792   -4.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9125   -3.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7375   -3.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8625   -4.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7667   -4.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4375   -2.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2542   -3.7000    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875   -1.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167   -2.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3125   -1.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  1  1  0
  5  4  1  0
  6  1  2  0
  7  3  2  0
  8  4  1  0
  9  6  1  0
 10  8  2  0
 11  8  1  0
 12 11  2  0
 13 10  1  0
 14 12  1  0
  3  5  1  0
 13 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA75703

   5-Iodomethylene-4-phenyl-dihydro-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: 300.10

Molecular Weight (Monoisotopic): 299.9647

AlogP: 2.99

#Rotatable Bonds: 1

Polar Surface Area: 26.30

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.43

CX LogD: 2.43

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.59

Np Likeness Score: 0.77

References

1. Sofia MJ, Katzenellenbogen JA..  (1986)  Enol lactone inhibitors of serine proteases. The effect of regiochemistry on the inactivation behavior of phenyl-substituted (halomethylene)tetra- and -dihydrofuranones and (halomethylene)tetrahydropyranones toward alpha-chymotrypsin: stable acyl enzyme intermediate.,  29  (2): [PMID:3512826] [10.1021/jm00152a011]

Source

Source(1):

• Scientific Literature