(+)-Isoaltholactone

ID: ALA2286359

PubChem CID: 11322205

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+/m0/s1

Standard InChI Key:  ZKIRVBNLJKGIEM-FTYKPCCVSA-N

Molfile:  

     RDKit          2D

 17 19  0  0  0  0  0  0  0  0999 V2000
   15.6622   -3.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4871   -3.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8988   -2.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4866   -1.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6585   -1.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2506   -2.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7250   -2.3252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2108   -2.9941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2111   -1.6564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9973   -1.9120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9958   -2.7372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7086   -3.1494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4235   -2.7374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4210   -1.9090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7075   -1.5005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9560   -3.7806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1400   -3.1500    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  1
  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:

   

   ALA2286359

   (+)-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