4-Ethoxy-3,3,5-tripropyldesmosdumotin C

ID: ALA1683261

PubChem CID: 53325484

Max Phase: Preclinical

Molecular Formula: C26H34O4

Molecular Weight: 410.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC1=C(OCC)C(CCC)(CCC)C(=O)/C(=C(O)\C=C\c2ccccc2)C1=O

Standard InChI:  InChI=1S/C26H34O4/c1-5-12-20-23(28)22(21(27)16-15-19-13-10-9-11-14-19)24(29)26(17-6-2,18-7-3)25(20)30-8-4/h9-11,13-16,27H,5-8,12,17-18H2,1-4H3/b16-15+,22-21+

Standard InChI Key:  MGUPFLQYOSVLKL-DYUKIBRESA-N

Molfile:  

     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
   28.1065   -4.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4095   -3.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2345   -3.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8199   -4.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1115   -5.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1115   -5.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8199   -6.2515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5325   -5.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5325   -5.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8199   -7.0765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2487   -4.6078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2469   -6.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2457   -7.0816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9624   -5.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9636   -5.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6793   -4.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3930   -5.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1120   -3.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3977   -3.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6781   -3.7881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3953   -4.6078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6815   -5.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3971   -6.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9672   -6.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0594   -3.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4691   -3.1727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5845   -3.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1707   -3.1727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6854   -5.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9688   -4.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
 15 16  1  0
 16 17  2  0
  8  9  1  0
  9  4  1  0
  4  3  1  0
  7 10  2  0
 16 20  1  0
 17  1  1  0
  1 18  2  0
 18 19  1  0
 19 20  2  0
  2  4  1  0
  5 21  1  0
  9 11  2  0
 21 22  1  0
  5  6  2  0
  6 23  1  0
 23 29  1  0
  8 12  2  0
 29 24  1  0
  3 25  1  0
 12 13  1  0
 25 26  1  0
  5  4  1  0
  2 27  1  0
 12 14  1  0
 27 28  1  0
  6  7  1  0
 14 15  2  0
 22 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1683261

   5-ethoxy-3-hydroxy-2-[(E)-3-phenylprop-2-enoyl]-4,6,6-tripropylcyclohexa-2,4-dien-1-one

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: 410.55

Molecular Weight (Monoisotopic): 410.2457

AlogP: 6.34

#Rotatable Bonds: 10

Polar Surface Area: 63.60

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.29

CX Basic pKa: ┄

CX LogP: 6.69

CX LogD: 3.72

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.28

Np Likeness Score: 0.90

References

1. Nakagawa-Goto K, Wu PC, Bastow KF, Yang SC, Yu SL, Chen HY, Lin JC, Goto M, Morris-Natschke SL, Yang PC, Lee KH..  (2011)  Antitumor agents 283. Further elaboration of desmosdumotin C analogs as potent antitumor agents: activation of spindle assembly checkpoint as possible mode of action.,  19  (5): [PMID:21296579] [10.1016/j.bmc.2011.01.001]

Source

Source(1):

• Scientific Literature