(1aR,7aS,10aS,10bS,E)-N,N-diethyl-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-carboxamide

ID: ALA4077243

PubChem CID: 137649088

Max Phase: Preclinical

Molecular Formula: C19H27NO4

Molecular Weight: 333.43

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H27NO4/c1-5-20(6-2)17(21)13-8-7-11-19(4)16(24-19)15-14(10-9-13)12(3)18(22)23-15/h8,14-16H,3,5-7,9-11H2,1-2,4H3/b13-8+/t14-,15-,16-,19+/m0/s1

Standard InChI Key:  KYJLYBHGLHGGNO-GDYLLAPZSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   32.0414   -3.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8930   -3.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4296   -2.5528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2495   -2.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7362   -3.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5615   -3.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8576   -3.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2123   -4.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5102   -5.2816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3397   -5.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5543   -4.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5221   -4.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7615   -4.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4214   -4.8732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5432   -5.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6359   -1.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4526   -1.8456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.3171   -4.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8542   -5.8727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.1086   -3.3431    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   33.9960   -5.2911    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   35.6427   -3.7682    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   33.2054   -1.1764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8831   -2.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8390   -1.1255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6558   -1.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6999   -2.5147    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
 16 23  2  0
 17 24  1  0
 17 25  1  0
 25 26  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4077243

   ---

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: 333.43

Molecular Weight (Monoisotopic): 333.1940

AlogP: 2.61

#Rotatable Bonds: 3

Polar Surface Area: 59.14

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.20

CX LogP: 2.62

CX LogD: 2.62

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.45

Np Likeness Score: 2.13

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