(1aR,7aS,10aS,10bS,E)-N,N,1a-trimethyl-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: ALA4071266

PubChem CID: 137638350

Max Phase: Preclinical

Molecular Formula: C17H23NO4

Molecular Weight: 305.37

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H23NO4/c1-10-12-8-7-11(15(19)18(3)4)6-5-9-17(2)14(22-17)13(12)21-16(10)20/h6,12-14H,1,5,7-9H2,2-4H3/b11-6+/t12-,13-,14-,17+/m0/s1

Standard InChI Key:  UEGIEAIEQXKRHD-CTUWAYRKSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   22.3342  -21.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1858  -20.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7224  -19.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5423  -19.6944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0289  -20.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8542  -20.3150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1503  -21.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5050  -21.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8029  -22.3848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6324  -22.3411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8470  -21.5387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8149  -21.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0542  -21.4791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7142  -21.9764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8360  -22.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9286  -18.9743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7454  -18.9488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.6098  -21.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1470  -22.9760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4014  -20.4463    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.2887  -22.3943    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.9355  -20.8714    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.4981  -18.2797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1759  -19.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1317  -18.2287    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
M  END

Alternative Forms

1. Parent:

   

   ALA4071266

   ---

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: 305.37

Molecular Weight (Monoisotopic): 305.1627

AlogP: 1.83

#Rotatable Bonds: 1

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: 0.03

CX LogP: 1.90

CX LogD: 1.90

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.42

Np Likeness Score: 2.50

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