((1aR,7aS,10aS,10bS,E)-1a-Methyl-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-yl)methyl thiophene-2-carboxylate

ID: ALA4063683

PubChem CID: 137635326

Max Phase: Preclinical

Molecular Formula: C20H22O5S

Molecular Weight: 374.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@H]2[C@H]1CC/C(COC(=O)c1cccs1)=C\CC[C@@]1(C)O[C@@H]21

Standard InChI:  InChI=1S/C20H22O5S/c1-12-14-8-7-13(11-23-19(22)15-6-4-10-26-15)5-3-9-20(2)17(25-20)16(14)24-18(12)21/h4-6,10,14,16-17H,1,3,7-9,11H2,2H3/b13-5+/t14-,16-,17-,20+/m0/s1

Standard InChI Key:  URTYVAMFQZSLCZ-KFMQRIMASA-N

Molfile:  

     RDKit          2D

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   29.5775  -18.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4291  -17.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9657  -16.6102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7856  -16.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2722  -17.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0975  -17.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3936  -18.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7483  -18.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0462  -19.3389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.8757  -19.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0903  -18.4928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0582  -18.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2975  -18.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9575  -18.9305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0792  -19.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1719  -15.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9887  -15.9029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8531  -18.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3903  -19.9301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.6447  -17.4004    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   31.5320  -19.3484    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   33.1788  -17.8255    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   32.3750  -15.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1918  -15.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9445  -14.4882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.6939  -15.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4629  -15.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4374  -14.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6527  -14.4796    0.0000 S   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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  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
 23 25  2  0
 24 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4063683

   ---

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: 374.46

Molecular Weight (Monoisotopic): 374.1188

AlogP: 3.66

#Rotatable Bonds: 3

Polar Surface Area: 65.13

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.20

CX LogD: 4.20

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.35

Np Likeness Score: 1.88

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