4-((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-carbonyl)piperazin-1-ium 2,2,2-trifluoroacetate

ID: ALA4088726

PubChem CID: 137644187

Max Phase: Preclinical

Molecular Formula: C21H27F3N2O6

Molecular Weight: 346.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@H]2[C@H]1CC/C(C(=O)N1CCNCC1)=C\CC[C@@]1(C)O[C@@H]21.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C19H26N2O4.C2HF3O2/c1-12-14-6-5-13(17(22)21-10-8-20-9-11-21)4-3-7-19(2)16(25-19)15(14)24-18(12)23;3-2(4,5)1(6)7/h4,14-16,20H,1,3,5-11H2,2H3;(H,6,7)/b13-4+;/t14-,15-,16-,19+;/m0./s1

Standard InChI Key:  ACTYTNNNGFRRLD-SKXDDKACSA-N

Molfile:  

     RDKit          2D

 35 37  0  0  0  0  0  0  0  0999 V2000
   27.7308   -3.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4386   -2.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1463   -3.3183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4386   -2.0925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0231   -2.9097    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.7308   -4.1355    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.0210   -3.7228    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.0370   -4.5454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8886   -3.7350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4252   -3.1141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2451   -3.1525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7318   -3.8161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5571   -3.7731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8532   -4.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2078   -5.0675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5058   -5.8429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   23.5177   -4.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7571   -4.9372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4170   -5.4345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5388   -5.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6315   -2.4324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4482   -2.4069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.3127   -4.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8498   -6.4340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1042   -3.9044    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.9916   -5.8524    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.6383   -4.3295    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.2010   -1.7378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8770   -3.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6903   -3.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0805   -2.3662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6512   -1.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8317   -1.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
 20  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 12 11  1  0
 19 15  1  0
 14 13  1  0
 13 12  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 14 18  1  0
 20 19  1  0
 21 20  1  0
 19 21  1  0
 20 22  1  1
 11 23  1  0
 23 24  1  0
 18 25  2  0
 17 26  2  0
 19 27  1  1
 15 28  1  1
 14 29  1  6
 23 30  2  0
 24 31  1  0
 24 35  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
M  END

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: 346.43

Molecular Weight (Monoisotopic): 346.1893

AlogP: 1.17

#Rotatable Bonds: 1

Polar Surface Area: 71.17

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.82

CX LogP: 1.37

CX LogD: 0.81

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.44

Np Likeness Score: 2.05

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