7-Oxa-phomopsolide E

ID: ALA4580864

PubChem CID: 11380976

Max Phase: Preclinical

Molecular Formula: C14H18O7

Molecular Weight: 298.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C/C=C(\C)C(=O)O[C@H]1C=CC(=O)O[C@H]1COC(=O)[C@H](C)O

Standard InChI:  InChI=1S/C14H18O7/c1-4-8(2)13(17)21-10-5-6-12(16)20-11(10)7-19-14(18)9(3)15/h4-6,9-11,15H,7H2,1-3H3/b8-4+/t9-,10-,11-/m0/s1

Standard InChI Key:  FKBITCOIJAFLNT-SPJFXFQZSA-N

Molfile:  

 
     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
   23.3951   -4.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3951   -5.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1045   -6.0435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8139   -5.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8139   -4.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1045   -4.4009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5269   -4.4071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5293   -3.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2424   -3.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9489   -3.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6619   -3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2448   -2.3538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8187   -3.1709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5252   -6.0486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2376   -5.6369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9447   -6.0507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6571   -5.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3684   -6.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6583   -4.8177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9435   -6.8720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6839   -6.0486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  6  2  0
  5  7  1  6
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  9 12  1  0
  8 13  2  0
  4 14  1  6
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  1
 16 20  2  0
  2 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4580864

   7-oxo-phomopsolide E

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 298.29

Molecular Weight (Monoisotopic): 298.1053

AlogP: 0.27

#Rotatable Bonds: 5

Polar Surface Area: 99.13

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.00

CX Basic pKa: ┄

CX LogP: 1.68

CX LogD: 1.68

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.44

Np Likeness Score: 2.58

References

1. Aljahdali AZ, Freedman SA, Scott J, Li M, O'Doherty GA..  (2019)  Synthesis and direct comparison of the anticancer activities of phomopsolides D and E and two 7-oxa-/7-aza-analogues.,  10  (7): [PMID:31391894] [10.1039/C9MD00121B]

Source

Source(1):

• Scientific Literature