Paecilomycin O

ID: ALA4211900

PubChem CID: 139589758

Max Phase: Preclinical

Molecular Formula: C19H20O7

Molecular Weight: 360.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(O)c2c(c1)[C@H]1O[C@@H]1CC1=C(O)C(=O)C[C@H]1C[C@H](C)OC2=O

Standard InChI:  InChI=1S/C19H20O7/c1-8-3-9-4-14(21)17(22)11(9)7-15-18(26-15)12-5-10(24-2)6-13(20)16(12)19(23)25-8/h5-6,8-9,15,18,20,22H,3-4,7H2,1-2H3/t8-,9+,15+,18+/m0/s1

Standard InChI Key:  ADTJGNWKVRRFSM-RTGCBJDCSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   13.2319   -3.6973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2308   -4.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9442   -4.9381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9423   -3.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6563   -3.6936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6552   -4.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3689   -3.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7901   -4.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7971   -3.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6589   -2.4568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5722   -2.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0033   -3.8039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0713   -1.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5102   -3.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5085   -4.5238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2938   -4.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7768   -4.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2966   -3.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5439   -5.5648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6007   -4.1191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0815   -4.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3668   -4.9358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0812   -5.3469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5080   -2.8775    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9399   -2.4631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5175   -4.9371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8006   -4.5225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3623   -5.7593    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.4874   -3.8019    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  7  1  0
  6 22  1  0
 21  8  1  0
  8 15  1  0
 14  9  1  0
  7 10  1  0
  9 11  1  0
 10 11  1  0
  7 12  2  0
 11 13  1  1
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
 16 19  1  0
 17 20  2  0
 22 21  1  0
 23 22  1  0
 21 23  1  0
 14 24  1  1
  4 25  1  0
  2 26  1  0
 26 27  1  0
 22 28  1  1
 21 29  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4211900

   ---

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: 360.36

Molecular Weight (Monoisotopic): 360.1209

AlogP: 2.58

#Rotatable Bonds: 1

Polar Surface Area: 105.59

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.27

CX Basic pKa: ┄

CX LogP: 2.31

CX LogD: 2.26

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.59

Np Likeness Score: 1.79

References

1. Xu L, Wu P, Xue J, Molnar I, Wei X..  (2017)  Antifungal and Cytotoxic β-Resorcylic Acid Lactones from a Paecilomyces Species.,  80  (8): [PMID:28749671] [10.1021/acs.jnatprod.7b00066]

Source

Source(1):

• Scientific Literature