((1aR,7aS,10aS,10bS,E)-1a-Methyl-8-methylene-9-oxo-1a,2,3,6,7,7a,8,9,10a, 10b-decahydrooxireno[2',3':9,10]cyclodeca[1,2-b]furan-5-yl)methyl cinnamate

ID: ALA4087934

PubChem CID: 137642970

Max Phase: Preclinical

Molecular Formula: C24H26O5

Molecular Weight: 394.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@H]2[C@H]1CC/C(COC(=O)/C=C/c1ccccc1)=C\CC[C@@]1(C)O[C@@H]21

Standard InChI:  InChI=1S/C24H26O5/c1-16-19-12-10-18(15-27-20(25)13-11-17-7-4-3-5-8-17)9-6-14-24(2)22(29-24)21(19)28-23(16)26/h3-5,7-9,11,13,19,21-22H,1,6,10,12,14-15H2,2H3/b13-11+,18-9+/t19-,21-,22-,24+/m0/s1

Standard InChI Key:  CEKHWTNKWWCPRP-FNCJUPDBSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   28.6488  -10.7734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5004   -9.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0370   -9.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8570   -9.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3436  -10.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1689  -10.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4650  -10.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8197  -11.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1176  -12.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9471  -12.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1617  -11.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1296  -10.8423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3689  -11.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0288  -11.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1506  -11.9525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2433   -8.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0601   -8.6349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.9245  -10.9316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4616  -12.6620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.7160  -10.1323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   30.6034  -12.0804    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   32.2502  -10.5575    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   31.4464   -7.9147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2632   -7.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0159   -7.2201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.6495   -7.1691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4663   -7.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8943   -7.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7104   -7.8117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0975   -7.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6625   -6.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8480   -6.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13  1  1  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  4  1  0
 12  8  1  0
  7  6  1  0
  6  5  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  7 11  1  0
 13 12  1  0
 14 13  1  0
 12 14  1  0
 13 15  1  1
  4 16  1  0
 16 17  1  0
 11 18  2  0
 10 19  2  0
 12 20  1  1
  8 21  1  1
  7 22  1  6
 17 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4087934

   ---

Molecule Features

Natural Product: No

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: 394.47

Molecular Weight (Monoisotopic): 394.1780

AlogP: 4.00

#Rotatable Bonds: 4

Polar Surface Area: 65.13

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.82

CX LogD: 4.82

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.33

Np Likeness Score: 2.41

References

1. Yang Z, Kuang B, Kang N, Ding Y, Ge W, Lian L, Gao Y, Wei Y, Chen Y, Zhang Q..  (2017)  Synthesis and anti-acute myeloid leukemia activity of C-14 modified parthenolide derivatives.,  127  [PMID:28068601] [10.1016/j.ejmech.2016.12.044]

2. Ge W, Hao X, Han F, Liu Z, Wang T, Wang M, Chen N, Ding Y, Chen Y, Zhang Q..  (2019)  Synthesis and structure-activity relationship studies of parthenolide derivatives as potential anti-triple negative breast cancer agents.,  166  [PMID:30739826] [10.1016/j.ejmech.2019.01.058]

Source

Source(1):

• Scientific Literature