Benzyl (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-carboxylate

ID: ALA4062619

PubChem CID: 137636880

Max Phase: Preclinical

Molecular Formula: C22H24O5

Molecular Weight: 368.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@H]2[C@H]1CC/C(C(=O)OCc1ccccc1)=C\CC[C@@]1(C)O[C@@H]21

Standard InChI:  InChI=1S/C22H24O5/c1-14-17-11-10-16(21(24)25-13-15-7-4-3-5-8-15)9-6-12-22(2)19(27-22)18(17)26-20(14)23/h3-5,7-9,17-19H,1,6,10-13H2,2H3/b16-9+/t17-,18-,19-,22+/m0/s1

Standard InChI Key:  JYNBENXIABLDLH-AWFLHDHLSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   22.1526   -4.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0042   -3.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5408   -2.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3607   -2.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8473   -3.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6726   -3.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9687   -4.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3234   -4.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6213   -5.5829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4508   -5.5391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6654   -4.7368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6333   -4.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8726   -4.6771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5326   -5.1745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6544   -5.4645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7470   -2.1724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5638   -2.1469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4282   -4.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9654   -6.1740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2198   -3.6443    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.1071   -5.5924    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.7539   -4.0694    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.9501   -1.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3165   -1.4777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7669   -1.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1961   -2.1003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0122   -2.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3993   -1.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9644   -0.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1498   -0.6862    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
 16 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4062619

   ---

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: 368.43

Molecular Weight (Monoisotopic): 368.1624

AlogP: 3.49

#Rotatable Bonds: 3

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: 4.37

CX LogD: 4.37

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.46

Np Likeness Score: 2.30

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]

Source

Source(1):

• Scientific Literature