(R)-8-[2-Benzyloxy-eth-(E)-ylidene]-4-hydroxy-hexahydro-pyrano[3,2-b]pyran-2-one

ID: ALA332207

PubChem CID: 44347032

Max Phase: Preclinical

Molecular Formula: C17H20O5

Molecular Weight: 304.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1CC(O)[C@H]2OCC/C(=C\COCc3ccccc3)C2O1

Standard InChI:  InChI=1S/C17H20O5/c18-14-10-15(19)22-16-13(7-9-21-17(14)16)6-8-20-11-12-4-2-1-3-5-12/h1-6,14,16-18H,7-11H2/b13-6+/t14?,16?,17-/m1/s1

Standard InChI Key:  VLZUAYCDIQBIGM-ZKENQSSOSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  1  0  0  0  0  0999 V2000
    6.5167   -3.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5167   -2.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2375   -3.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9542   -3.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9542   -2.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2375   -2.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8042   -3.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8042   -2.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6667   -3.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8042   -4.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2375   -1.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0917   -2.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0917   -3.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9542   -4.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3792   -4.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0917   -5.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6625   -5.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -5.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9542   -3.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -3.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5250   -4.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5250   -3.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5214   -1.7167    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  3  1  0
  5  4  1  0
  2  6  1  0
  7  1  1  0
  8  2  1  0
  9  4  2  0
 10  7  2  0
 11  6  1  0
 12 13  1  0
 13  7  1  0
 14 17  1  0
 15 16  1  0
 16 10  1  0
 17 15  1  0
 18 14  1  0
 19 14  2  0
 20 19  1  0
 21 18  2  0
 22 20  2  0
  6  5  1  0
  8 12  1  0
 21 22  1  0
  2 23  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA332207

   (4aR,8E)-4-hydroxy-8-(2-phenylmethoxyethylidene)-3,4,4a,6,7,8a-hexahydropyrano[3,2-b]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: 304.34

Molecular Weight (Monoisotopic): 304.1311

AlogP: 1.59

#Rotatable Bonds: 4

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: 13.84

CX Basic pKa: ┄

CX LogP: 1.28

CX LogD: 1.28

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.52

Np Likeness Score: 1.43

References

1. Bessodes M, Shamsazar J, Antonakis K, Lafarge-Frayssinet C, Frayssinet C.  (1991)  Studies on the macrocyclic part of the trichothecene satratoxin: partial synthesis and structure-activity relationship,  1  (7): [10.1016/S0960-894X(01)80473-X]

Source

Source(1):

• Scientific Literature