(3aS,5S,9aR,10aS,10bS,E)-6,9a-Dimethyl-3-methylene-2-oxo-2,3,3a,4,5,8,9,9a,10a,10b-decahydrooxireno[2',3':9,10]cyclodeca[1,2-b]furan-5-yl(2,4-difluorophenyl)carbamate

ID: ALA4228003

PubChem CID: 145968884

Max Phase: Preclinical

Molecular Formula: C22H23F2NO5

Molecular Weight: 419.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@@H]2[C@H]3O[C@]3(C)CC/C=C(/C)[C@@H](OC(=O)Nc3ccc(F)cc3F)C[C@@H]12

Standard InChI:  InChI=1S/C22H23F2NO5/c1-11-5-4-8-22(3)19(30-22)18-14(12(2)20(26)29-18)10-17(11)28-21(27)25-16-7-6-13(23)9-15(16)24/h5-7,9,14,17-19H,2,4,8,10H2,1,3H3,(H,25,27)/b11-5+/t14-,17-,18-,19+,22+/m0/s1

Standard InChI Key:  KZSKDDFTFNHQOP-IWKDOLOKSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    5.6418   -3.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162   -5.6116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7936   -6.4233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5005   -4.3766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7917   -5.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9183   -6.0241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2156   -6.3345    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3608   -4.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9260   -4.3766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8071   -6.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0301   -7.2405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2060   -4.7912    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6313   -5.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2277   -3.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5005   -5.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1584   -4.9932    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3581   -5.2137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9205   -5.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6136   -6.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9678   -5.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6509   -4.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6455   -3.1374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3602   -2.7291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3639   -1.9060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0710   -3.1438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7857   -2.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4957   -3.1531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2099   -2.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2140   -1.9215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4981   -1.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7869   -1.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0746   -1.5047    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.9281   -1.5123    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  3 19  1  0
  9 21  1  0
  4 15  1  0
 15  2  1  0
 19 11  2  0
  4 14  1  0
 20  5  2  0
  9  1  1  0
  8  1  1  0
 18  6  1  0
 18 13  1  0
 18 12  1  6
  9 14  2  0
 19 20  1  0
 17 20  1  0
  2 10  1  1
 13  3  1  0
  6  2  1  0
  2 18  1  0
 17 13  1  0
 13  7  1  1
 17 16  1  6
 17  8  1  0
  1 22  1  1
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 31 32  1  0
 29 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4228003

   ---

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: 419.42

Molecular Weight (Monoisotopic): 419.1544

AlogP: 4.27

#Rotatable Bonds: 2

Polar Surface Area: 77.16

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.03

CX Basic pKa: ┄

CX LogP: 4.47

CX LogD: 4.47

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.34

Np Likeness Score: 1.58

References

1. Alwaseem H, Frisch BJ, Fasan R..  (2018)  Anticancer activity profiling of parthenolide analogs generated via P450-mediated chemoenzymatic synthesis.,  26  (7): [PMID:28826596] [10.1016/j.bmc.2017.08.009]

Source

Source(1):

• Scientific Literature