rac-Pestalalactone

ID: ALA2408959

PubChem CID: 73353614

Max Phase: Preclinical

Molecular Formula: C21H20Cl2O6

Molecular Weight: 439.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(Cl)c(C)c(Cl)c(O)c1C1OC(=O)c2c(O)cc(O)c(CC=C(C)C)c21

Standard InChI:  InChI=1S/C21H20Cl2O6/c1-8(2)5-6-10-11(24)7-12(25)14-13(10)19(29-21(14)27)15-18(26)16(22)9(3)17(23)20(15)28-4/h5,7,19,24-26H,6H2,1-4H3

Standard InChI Key:  AMZVUHJBCYQCJF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   34.5536   -5.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5524   -5.9525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2673   -6.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9837   -5.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2654   -4.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9780   -5.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5903   -4.5742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2560   -3.8218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.4374   -3.9073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3971   -4.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.6995   -6.3622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8376   -6.3644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8390   -4.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1246   -5.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4100   -4.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6957   -5.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4098   -3.8881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8858   -3.2937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1453   -2.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5945   -1.8982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7864   -2.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5321   -2.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0845   -3.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8326   -4.2537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.9529   -2.3429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.2107   -1.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7255   -3.0319    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   34.8505   -1.1140    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   33.2341   -1.4560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  1  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  7 10  2  0
  4 11  1  0
  2 12  1  0
  1 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
  9 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 23 24  1  0
 19 25  1  0
 25 26  1  0
 22 27  1  0
 20 28  1  0
 21 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2408959

   RAC-PESTALALACTONE

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: 439.29

Molecular Weight (Monoisotopic): 438.0637

AlogP: 5.20

#Rotatable Bonds: 4

Polar Surface Area: 96.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.11

CX Basic pKa: ┄

CX LogP: 6.34

CX LogD: 5.85

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.45

Np Likeness Score: 1.87

References

1. Augner D, Krut O, Slavov N, Gerbino DC, Sahl HG, Benting J, Nising CF, Hillebrand S, Krönke M, Schmalz HG..  (2013)  On the antibiotic and antifungal activity of pestalone, pestalachloride A, and structurally related compounds.,  76  (8): [PMID:23905700] [10.1021/np400301d]

Source

Source(1):

• Scientific Literature