(1aR,7aS,10aS,10bS,E)-5-(((4-methoxybenzyl)oxy)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: ALA4082766

PubChem CID: 137648613

Max Phase: Preclinical

Molecular Formula: C23H28O5

Molecular Weight: 384.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@H]2[C@H]1CC/C(COCc1ccc(OC)cc1)=C\CC[C@@]1(C)O[C@@H]21

Standard InChI:  InChI=1S/C23H28O5/c1-15-19-11-8-16(13-26-14-17-6-9-18(25-3)10-7-17)5-4-12-23(2)21(28-23)20(19)27-22(15)24/h5-7,9-10,19-21H,1,4,8,11-14H2,2-3H3/b16-5+/t19-,20-,21-,23+/m0/s1

Standard InChI Key:  TYUJVQRQKHBPIB-YVZRFNHLSA-N

Molfile:  

     RDKit          2D

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   12.0699   -3.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6066   -2.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.9131   -3.6593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7384   -3.6162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0345   -4.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3892   -4.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6871   -5.6861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5166   -5.6423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7312   -4.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6991   -4.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9384   -4.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5983   -5.2777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7201   -5.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8128   -2.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6296   -2.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   16.0311   -6.2772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2855   -3.7475    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1729   -5.6956    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.8197   -4.1726    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.0159   -1.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8327   -1.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2619   -2.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0779   -2.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4651   -1.4576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0301   -0.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2155   -0.7894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2818   -1.4311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7132   -2.1251    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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  3  4  2  0
  5  4  1  0
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  7  6  1  0
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 12 14  1  0
 13 15  1  1
  4 16  1  0
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 11 18  2  0
 10 19  2  0
 12 20  1  1
  8 21  1  1
  7 22  1  6
 17 23  1  0
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 24 25  2  0
 25 26  1  0
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 27 28  1  0
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 27 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4082766

   ---

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: 384.47

Molecular Weight (Monoisotopic): 384.1937

AlogP: 3.97

#Rotatable Bonds: 5

Polar Surface Area: 57.29

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.00

CX LogD: 4.00

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.33

Np Likeness Score: 2.11

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