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

ID: ALA4077129

PubChem CID: 137651891

Max Phase: Preclinical

Molecular Formula: C22H26O4

Molecular Weight: 354.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@H]2[C@H]1CC/C(COCc1ccccc1)=C\CC[C@@]1(C)O[C@@H]21

Standard InChI:  InChI=1S/C22H26O4/c1-15-18-11-10-17(14-24-13-16-7-4-3-5-8-16)9-6-12-22(2)20(26-22)19(18)25-21(15)23/h3-5,7-9,18-20H,1,6,10-14H2,2H3/b17-9+/t18-,19-,20-,22+/m0/s1

Standard InChI Key:  NHLGMBLHBDHDRU-NGWYOTLMSA-N

Molfile:  

     RDKit          2D

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    3.0231  -11.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5597  -10.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3796  -10.9818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8662  -11.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6915  -11.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9876  -12.3739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3423  -12.8969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6402  -13.6722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4697  -13.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6843  -12.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6522  -12.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8915  -12.7665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5514  -13.2638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6732  -13.5538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7659  -10.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5827  -10.2362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4471  -12.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9842  -14.2634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2387  -11.7337    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1260  -13.6818    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7728  -12.1588    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9690   -9.5161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7858   -9.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2128  -10.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0289  -10.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4160   -9.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9811   -8.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1665   -8.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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  5  4  1  0
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  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
 17 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4077129

   ---

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: 354.45

Molecular Weight (Monoisotopic): 354.1831

AlogP: 3.96

#Rotatable Bonds: 4

Polar Surface Area: 48.06

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.16

CX LogD: 4.16

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.36

Np Likeness Score: 2.28

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