(-)-altholactone

ID: ALA599777

PubChem CID: 10466465

Max Phase: Preclinical

Molecular Formula: C13H12O4

Molecular Weight: 232.24

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (-)-Altholactone | (-)-altholactone|CHEMBL599777

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-IXOXFDKPSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   -3.9253   -8.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9264   -9.5805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2110   -9.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4941   -9.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4969   -8.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2128   -8.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7815   -9.9937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5495  -10.7861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0994   -9.5283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0542  -11.4395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4460  -10.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7205  -10.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1884  -11.4315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6208  -11.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8953  -10.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3605   -9.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2335   -9.2320    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1564  -11.9118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9382  -11.6046    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  1  0
  7  4  1  6
  4  5  1  0
  8 10  1  1
 11 12  1  0
  2  3  1  0
  5  6  2  0
  6  1  1  0
  7  8  1  0
  1  2  2  0
  3  4  2  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 11 17  1  1
  8 12  1  0
 14 18  2  0
 11  9  1  0
 12 19  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA599777

   ENT-ALTHOLACTONE

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. Gupta S, Poeppelman L, Hinman CL, Bretz J, Hudson RA, Tillekeratne LM..  (2010)  Apoptotic activities in closely related styryllactone stereoisomers toward human tumor cell lines: Investigation of synergism of styryllactone-induced apoptosis with TRAIL.,  18  (2): [PMID:20036566] [10.1016/j.bmc.2009.11.045]

2. 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