13-desmethylene-17-desmethyl dactylolide

ID: ALA4474575

PubChem CID: 155537126

Max Phase: Preclinical

Molecular Formula: C21H26O5

Molecular Weight: 358.43

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H26O5/c1-16-6-2-13-21(24)26-20(15-22)12-5-11-19-10-4-9-18(25-19)8-3-7-17(23)14-16/h2-3,5-7,11,13,15,18-20H,4,8-10,12,14H2,1H3/b7-3+,11-5+,13-2+,16-6-/t18-,19-,20-/m0/s1

Standard InChI Key:  FWXBAKUCYNFJLA-YIOXLTTFSA-N

Molfile:  

 
     RDKit          2D

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    5.8257  -18.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5419  -18.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2582  -18.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2582  -17.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5419  -16.9771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9742  -16.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9774  -16.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6935  -15.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6966  -14.9283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4127  -14.5185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9837  -14.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9868  -13.6880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2740  -13.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5578  -13.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8450  -13.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1289  -13.6771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4160  -13.2619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1257  -14.5022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4096  -14.9120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4065  -15.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1194  -16.1523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1162  -16.9772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8291  -17.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6967  -14.4967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6999  -13.6717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7029  -13.2782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2503  -16.5715    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8210  -16.5674    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 23  1  1  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
 23  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 19 24  1  1
 24 25  2  0
 12 26  1  0
  4 27  1  6
 23 28  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4474575

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 358.43

Molecular Weight (Monoisotopic): 358.1780

AlogP: 3.40

#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: 3.46

CX LogD: 3.46

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.41

Np Likeness Score: 2.73

References

1. 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