Pestalachloride B

ID: ALA513378

PubChem CID: 44562122

Max Phase: Preclinical

Molecular Formula: C20H18Cl2O5

Molecular Weight: 409.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)=CCc1c(O)cc(O)c2c1C(=O)c1c(O)c(Cl)c(C)c(Cl)c1OC2

Standard InChI:  InChI=1S/C20H18Cl2O5/c1-8(2)4-5-10-12(23)6-13(24)11-7-27-20-15(18(25)14(10)11)19(26)16(21)9(3)17(20)22/h4,6,23-24,26H,5,7H2,1-3H3

Standard InChI Key:  XCFFTGALQWABRD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    4.8045   -1.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1021   -2.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9177   -2.3849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3194   -0.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2483   -1.9793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4396   -1.7431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1342   -0.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5685   -0.2135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3608   -0.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9658   -0.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9423   -1.4663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6347   -1.8919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3509   -1.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3705   -0.6871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6775   -0.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0193   -0.0755    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9893   -1.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5842   -2.9001    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.2136   -3.1550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3929   -2.7915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0544   -1.9353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6976    0.5596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6118   -2.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3146   -3.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2918   -3.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9946   -4.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5662   -4.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  0
  1  2  2  0
 13 14  1  0
  7  4  2  0
 14 15  2  0
 15 10  1  0
  5 11  1  0
  4 16  1  0
  5  6  1  0
  1 17  1  0
  7  8  1  0
  2 18  1  0
  8  9  1  0
  3 19  1  0
  9 10  1  0
  5 20  2  0
  6  7  1  0
 13 21  1  0
  4  1  1  0
 15 22  1  0
 12 23  1  0
 10 11  2  0
 23 24  1  0
  2  3  1  0
 24 25  2  0
 11 12  1  0
 25 26  1  0
  3  6  2  0
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA513378

   PESTALACHLORIDE B

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: 409.27

Molecular Weight (Monoisotopic): 408.0531

AlogP: 5.05

#Rotatable Bonds: 2

Polar Surface Area: 86.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.26

CX Basic pKa: ┄

CX LogP: 6.22

CX LogD: 5.81

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.60

Np Likeness Score: 1.64

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. Wang W, Park C, Oh E, Sung Y, Lee J, Park KH, Kang H..  (2019)  Benzophenone Compounds, from a Marine-Derived Strain of the Fungus Pestalotiopsis neglecta, Inhibit Proliferation of Pancreatic Cancer Cells by Targeting the MEK/ERK Pathway.,  82  (12): [PMID:31829592] [10.1021/acs.jnatprod.9b00646]

Source

Source(1):

• Scientific Literature