ent-isoaltholactone

ID: ALA2286358

PubChem CID: 13872804

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-JHEVNIALSA-N

Molfile:  

     RDKit          2D

 17 19  0  0  0  0  0  0  0  0999 V2000
   22.7036   -3.0497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5285   -3.0508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9403   -2.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5280   -1.6238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7000   -1.6266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2920   -2.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7666   -2.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2524   -3.0068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2527   -1.6691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0390   -1.9246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0374   -2.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7503   -3.1621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4652   -2.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4627   -1.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7493   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9975   -3.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.1817   -3.1627    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  6
 12 13  1  0
 13 14  1  0
 14 15  2  0
 10 15  1  0
  8 16  1  6
 13 17  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2286358

   ENT-ISOALTHOLACTONE

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