(-)-Dactylolide

ID: ALA4288175

PubChem CID: 11222845

Max Phase: Preclinical

Molecular Formula: C23H28O5

Molecular Weight: 384.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C[C@@H]2C/C=C/C(=O)C/C(C)=C\C=C\C(=O)O[C@H](C=O)C/C(C)=C/[C@H](C1)O2

Standard InChI:  InChI=1S/C23H28O5/c1-16-6-4-9-23(26)28-22(15-24)14-18(3)13-21-12-17(2)11-20(27-21)8-5-7-19(25)10-16/h4-7,9,13,15,20-22H,2,8,10-12,14H2,1,3H3/b7-5+,9-4+,16-6-,18-13+/t20-,21-,22-/m0/s1

Standard InChI Key:  JSRXONXXGPZPDD-WVXVWMMWSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
    6.1496  -14.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8549  -13.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5601  -14.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9722  -14.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2657  -13.7981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1496  -15.0231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4505  -15.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4506  -16.2418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9687  -15.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6648  -16.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6723  -15.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1558  -16.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1542  -17.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9554  -16.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9478  -17.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5385  -17.4474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8590  -17.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8761  -18.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5712  -19.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2507  -18.6216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2351  -17.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6821  -13.8071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3824  -15.0331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5877  -19.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8628  -16.2337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4407  -13.7994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7422  -15.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7410  -14.2047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8512  -17.0413    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2297  -17.0042    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4438  -14.6104    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0
  1  2  1  0
  3  2  2  0
  3  5  1  0
  9  4  1  0
  4  5  2  0
  7  6  1  0
  7  8  1  0
  8 12  1  0
  9 11  1  0
 14 10  2  0
 10 11  1  0
 12 13  2  0
 13 17  1  0
 14 15  1  0
 21 15  1  0
 16 17  1  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  4 22  1  0
 11 23  2  0
 19 24  2  0
 12 25  1  0
  1 26  2  0
  7 27  1  0
 27 28  2  0
 17 29  1  6
 21 30  1  6
  7 31  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4288175

   (-)-Dactylolide

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: 3.96

#Rotatable Bonds: 1

Polar Surface Area: 69.67

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.65

CX LogD: 3.65

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.39

Np Likeness Score: 2.76

References

1. Cao YN, Zheng LL, Wang D, Liang XX, Gao F, Zhou XL..  (2018)  Recent advances in microtubule-stabilizing agents.,  143  [PMID:29223097] [10.1016/j.ejmech.2017.11.062]

2. Taufa T, Singh AJ, Harland CR, Patel V, Jones B, Halafihi TI, Miller JH, Keyzers RA, Northcote PT..  (2018)  Zampanolides B-E from the Marine Sponge Cacospongia mycofijiensis: Potent Cytotoxic Macrolides with Microtubule-Stabilizing Activity.,  81  (11): [PMID:30371079] [10.1021/acs.jnatprod.8b00641]

3. Henry JL, Wilson MR, Mulligan MP, Quinn TR, Sackett DL, Taylor RE..  (2019)  Synthesis, conformational preferences, and biological activity of conformational analogues of the microtubule-stabilizing agents, (-)-zampanolide and (-)-dactylolide.,  10  (5): [PMID:31191870] [10.1039/C9MD00164F]

Source

Source(1):

• Scientific Literature