6-Iodomethylene-5-phenyl-tetrahydro-pyran-2-one

ID: ALA310682

PubChem CID: 13553454

Max Phase: Preclinical

Molecular Formula: C12H11IO2

Molecular Weight: 314.12

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1CCC(c2ccccc2)/C(=C\I)O1

Standard InChI:  InChI=1S/C12H11IO2/c13-8-11-10(6-7-12(14)15-11)9-4-2-1-3-5-9/h1-5,8,10H,6-7H2/b11-8+

Standard InChI Key:  YRQGHLWYPKIKJR-DHZHZOJOSA-N

Molfile:  

     RDKit          2D

 15 16  0  0  0  0  0  0  0  0999 V2000
    2.9167   -4.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7375   -4.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -3.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500   -3.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9167   -3.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -5.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9750   -3.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6792   -3.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417   -3.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6792   -5.2417    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667   -3.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2750   -4.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4500   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4417   -3.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0292   -3.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6  1  2  0
  7  4  2  0
  8  3  1  0
  9  5  1  0
 10  6  1  0
 11  8  2  0
 12  8  1  0
 13 12  2  0
 14 11  1  0
 15 13  1  0
  4  9  1  0
 14 15  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA310682

   6-Iodomethylene-5-phenyl-tetrahydro-pyran-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: 314.12

Molecular Weight (Monoisotopic): 313.9804

AlogP: 3.38

#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: 2.88

CX LogD: 2.88

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.59

Np Likeness Score: 0.94

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