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

ID: ALA4062240

PubChem CID: 137635694

Max Phase: Preclinical

Molecular Formula: C19H25NO4

Molecular Weight: 331.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@H]2[C@H]1CC/C(C(=O)N1CCCC1)=C\CC[C@@]1(C)O[C@@H]21

Standard InChI:  InChI=1S/C19H25NO4/c1-12-14-8-7-13(17(21)20-10-3-4-11-20)6-5-9-19(2)16(24-19)15(14)23-18(12)22/h6,14-16H,1,3-5,7-11H2,2H3/b13-6+/t14-,15-,16-,19+/m0/s1

Standard InChI Key:  JLALAWOIVFYLTJ-FKUVIKGSSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    2.7505   -4.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6021   -3.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1387   -2.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9586   -2.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4452   -3.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2705   -3.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5666   -4.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9213   -4.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2192   -5.6365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0487   -5.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2633   -4.7904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2312   -4.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4705   -4.7308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1305   -5.2281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2523   -5.5181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3449   -2.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1617   -2.2005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0261   -4.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5633   -6.2277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8177   -3.6980    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7050   -5.6460    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3518   -4.1231    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9144   -1.5314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6604   -2.8499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4293   -2.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4038   -1.7564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6191   -1.5283    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
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4062240

   ---

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: 331.41

Molecular Weight (Monoisotopic): 331.1784

AlogP: 2.36

#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: 0.20

CX LogP: 2.31

CX LogD: 2.31

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.42

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