(1aR,7aS,10aS,10bS,E)-1a-Methyl-8-methylene-5-(morpholine-4-carbonyl)-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2',3':9,10]cyclodeca[1,2-b]furan-9(1aH)-one

ID: ALA4061534

PubChem CID: 137636164

Max Phase: Preclinical

Molecular Formula: C19H25NO5

Molecular Weight: 347.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@H]2[C@H]1CC/C(C(=O)N1CCOCC1)=C\CC[C@@]1(C)O[C@@H]21

Standard InChI:  InChI=1S/C19H25NO5/c1-12-14-6-5-13(17(21)20-8-10-23-11-9-20)4-3-7-19(2)16(25-19)15(14)24-18(12)22/h4,14-16H,1,3,5-11H2,2H3/b13-4+/t14-,15-,16-,19+/m0/s1

Standard InChI Key:  FJDOLZDWPAFLGY-ZJQQOWBJSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   12.6476  -12.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4992  -11.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0358  -10.6463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8557  -10.6847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3423  -11.3483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1676  -11.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4637  -12.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8184  -12.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1163  -13.3751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9458  -13.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1604  -12.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1283  -12.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3676  -12.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0276  -12.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1494  -13.2567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2420   -9.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0588   -9.9391    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9232  -12.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4604  -13.9662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7148  -11.4366    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.6021  -13.3846    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.2489  -11.8617    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.8115   -9.2699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4852  -10.6364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2985  -10.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6887   -9.8946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2594   -9.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4399   -9.2201    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 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4061534

   ---

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: 347.41

Molecular Weight (Monoisotopic): 347.1733

AlogP: 1.60

#Rotatable Bonds: 1

Polar Surface Area: 68.37

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.18

CX LogP: 1.68

CX LogD: 1.68

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.41

Np Likeness Score: 1.79

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