ID: ALA489144

Max Phase: Preclinical

Molecular Formula: C21H20Cl2O6

Molecular Weight: 439.29

Molecule Type: Small molecule

Representations

Synonyms (1): Pestalone
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1c(Cl)c(C)c(Cl)c(O)c1C(=O)c1c(C=O)c(O)cc(O)c1CC=C(C)C

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

Standard InChI Key:  ACRANQNXYMAQKJ-UHFFFAOYSA-N

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

Properties

Molecular Weight: 439.29

Molecular Weight (Monoisotopic): 438.0637

AlogP: 4.98

#Rotatable Bonds: 6

Polar Surface Area: 104.06

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 5.38

CX Basic pKa:

CX LogP: 6.83

CX LogD: 4.31

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.33

Np Likeness Score: 1.66

References

1. Cueto M, Jensen PR, Kauffman C, Fenical W, Lobkovsky E, Clardy J..  (2001)  Pestalone, a new antibiotic produced by a marine fungus in response to bacterial challenge.,  64  (11): [PMID:11720529] [10.1021/np0102713]

2. Zhang C, Ondeyka JG, Herath KB, Guan Z, Collado J, Platas G, Pelaez F, Leavitt PS, Gurnett A, Nare B, Liberator P, Singh SB..  (2005)  Tenellones A and B from a Diaporthe sp.: two highly substituted benzophenone inhibitors of parasite cGMP-dependent protein kinase activity.,  68  (4): [PMID:15844962] [10.1021/np049591n]

3. 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]

4. 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