Pestalachloride A

ID: ALA470091

PubChem CID: 44562121

Max Phase: Preclinical

Molecular Formula: C21H21Cl2NO5

Molecular Weight: 438.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(Cl)c(C)c(Cl)c(O)c1C1NC(=O)c2c(O)cc(O)c(CC=C(C)C)c21

Standard InChI:  InChI=1S/C21H21Cl2NO5/c1-8(2)5-6-10-11(25)7-12(26)14-13(10)18(24-21(14)28)15-19(27)16(22)9(3)17(23)20(15)29-4/h5,7,18,25-27H,6H2,1-4H3,(H,24,28)

Standard InChI Key:  IFONQCDBHMGEFN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    0.6789   -1.7444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3953   -1.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3925   -0.5005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6771   -0.0914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0359   -1.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0347   -0.5072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8183   -0.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039   -0.9174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8206   -1.5851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0720    0.5338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2167   -2.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0400   -2.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4360   -3.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0072   -3.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1782   -3.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7859   -3.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4680   -1.6209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2928   -1.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2608   -3.0675    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4023   -4.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7470   -4.4366    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6787   -2.5694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0359   -2.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3931   -2.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3929   -3.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1072   -4.2197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6783   -4.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1105   -1.7424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6733    0.7336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  2  0
 14 15  1  0
  3  4  2  0
 15 16  2  0
 16 11  1  0
 16 23  1  0
  6  7  1  0
 12 17  1  0
  7  8  1  0
 17 18  1  0
  8  9  1  0
 13 19  1  0
  9  5  1  0
 14 20  1  0
  4  6  1  0
 15 21  1  0
  7 10  2  0
  1 22  1  0
  5  6  2  0
  9 11  1  0
 22 24  1  0
  1  2  2  0
 24 25  2  0
 11 12  2  0
 25 26  1  0
  5  1  1  0
 25 27  1  0
 12 13  1  0
  2 28  1  0
  2  3  1  0
  4 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA470091

   PESTALACHLORIDE A

Molecule Features

Natural Product: Yes

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: 438.31

Molecular Weight (Monoisotopic): 437.0797

AlogP: 4.77

#Rotatable Bonds: 4

Polar Surface Area: 99.02

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.15

CX Basic pKa: ┄

CX LogP: 5.61

CX LogD: 5.10

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.52

Np Likeness Score: 1.66

References

1. Li E, Jiang L, Guo L, Zhang H, Che Y..  (2008)  Pestalachlorides A-C, antifungal metabolites from the plant endophytic fungus Pestalotiopsis adusta.,  16  (17): [PMID:18694644] [10.1016/j.bmc.2008.07.075]

2. 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