(1aR,7aS,10aS,10bS,E)-5-(benzo[d]thiazol-2-yl)-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: ALA4073455

PubChem CID: 137641130

Max Phase: Preclinical

Molecular Formula: C21H21NO3S

Molecular Weight: 367.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@H]2[C@H]1CC/C(c1nc3ccccc3s1)=C\CC[C@@]1(C)O[C@@H]21

Standard InChI:  InChI=1S/C21H21NO3S/c1-12-14-10-9-13(19-22-15-7-3-4-8-16(15)26-19)6-5-11-21(2)18(25-21)17(14)24-20(12)23/h3-4,6-8,14,17-18H,1,5,9-11H2,2H3/b13-6+/t14-,17-,18-,21+/m0/s1

Standard InChI Key:  DFIWENFHZYGLHR-LQKMXSOBSA-N

Molfile:  

     RDKit          2D

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   13.2460  -12.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0976  -11.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6342  -10.8609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4541  -10.8993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9408  -11.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7661  -11.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0622  -12.2914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4169  -12.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7148  -13.5897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5443  -13.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7589  -12.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7267  -12.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9661  -12.6840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6260  -13.1813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7478  -13.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8405  -10.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5217  -12.4504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0588  -14.1808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3132  -11.6512    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.2006  -13.5992    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.8473  -12.0763    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.6465  -10.0673    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4814   -9.4423    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.0712   -8.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7869   -9.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4782   -8.8383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4551   -8.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7348   -7.6395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0464   -8.0677    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
 11 17  2  0
 10 18  2  0
 12 19  1  1
  8 20  1  1
  7 21  1  6
 16 22  2  0
 22 25  1  0
 24 23  1  0
 23 16  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:

   

   ALA4073455

   ---

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: 367.47

Molecular Weight (Monoisotopic): 367.1242

AlogP: 4.51

#Rotatable Bonds: 1

Polar Surface Area: 51.72

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.09

CX LogP: 4.86

CX LogD: 4.86

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.42

Np Likeness Score: 1.53

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