(2R,3S,3aS,7aR)-3-hydroxy-2-phenyl-3,3a-dihydro-2H-furo[3,2-b]pyran-5(7aH)-one

ID: ALA2286356

PubChem CID: 13872802

Max Phase: Preclinical

Molecular Formula: C13H12O4

Molecular Weight: 232.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C=C[C@H]2O[C@H](c3ccccc3)[C@H](O)[C@@H]2O1

Standard InChI:  InChI=1S/C13H12O4/c14-10-7-6-9-13(17-10)11(15)12(16-9)8-4-2-1-3-5-8/h1-7,9,11-13,15H/t9-,11+,12-,13-/m1/s1

Standard InChI Key:  ZKIRVBNLJKGIEM-GWNIPJSYSA-N

Molfile:  

     RDKit          2D

 17 19  0  0  0  0  0  0  0  0999 V2000
    8.1217   -7.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9466   -7.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3583   -6.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9461   -5.9498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1180   -5.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7101   -6.6659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1846   -6.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6705   -7.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6708   -5.9951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4570   -6.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4556   -7.0759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1684   -7.4881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8832   -7.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8807   -6.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1673   -5.8392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4157   -8.1193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5998   -7.4887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  1  0
  8 11  1  0
 10  9  1  6
  9  7  1  0
  7  3  1  1
 10 11  1  0
 11 12  1  1
 12 13  1  0
 13 14  1  0
 14 15  2  0
 10 15  1  0
  8 16  1  1
 13 17  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2286356

   (2R,3S,3aS,7aR)-3-hydroxy-2-phenyl-2,3,3a,7a-tetrahydrofuro[3,2-b]pyran-5-one

Molecule Features

Natural Product: Yes

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: 232.24

Molecular Weight (Monoisotopic): 232.0736

AlogP: 0.97

#Rotatable Bonds: 1

Polar Surface Area: 55.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.99

CX Basic pKa: ┄

CX LogP: 1.59

CX LogD: 1.59

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.73

Np Likeness Score: 2.45

References

1. HIRATATE A, KIYOTA H, NOSHITA T, TAKEUCHI R, ORITANI T.  (2001)  Synthesis of Both Enantiomers of Altholactone, Isoaltholactone and 5-Hydroxygoniothalamin from Tri-O-acetyl-D-glucal, and Their Biological Activities,  26  (4): [10.1584/jpestics.26.366]

Source

Source(1):

• Scientific Literature