Pestynol

ID: ALA4165878

PubChem CID: 139590070

Max Phase: Preclinical

Molecular Formula: C21H30O4

Molecular Weight: 346.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C#CC1=C[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O)CC/C=C(\C)CCC=C(C)C

Standard InChI:  InChI=1S/C21H30O4/c1-14(2)7-5-8-15(3)9-6-10-16(4)11-12-17-13-18(22)20(24)21(25)19(17)23/h7,9,13,18-25H,4-6,8,10H2,1-3H3/b15-9+/t18-,19-,20-,21-/m1/s1

Standard InChI Key:  CADYTUXNRNXAES-NYJGJKORSA-N

Molfile:  

     RDKit          2D

 25 25  0  0  0  0  0  0  0  0999 V2000
    2.8437   -4.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5514   -4.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1360   -4.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8437   -5.7038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2591   -4.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9668   -4.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6745   -4.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3822   -4.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6745   -5.7038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0899   -4.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7976   -4.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5053   -4.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2130   -4.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5053   -5.7038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9177   -4.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6211   -3.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3352   -4.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0364   -3.6393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0320   -2.8218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3202   -2.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6127   -2.8328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9017   -2.4300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3143   -1.6013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7369   -2.4084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7469   -4.0431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  3  1  0
  1  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  3  0
 15 16  1  0
 16 17  2  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 20 23  1  1
 19 24  1  6
 18 25  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4165878

   ---

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: 346.47

Molecular Weight (Monoisotopic): 346.2144

AlogP: 2.40

#Rotatable Bonds: 6

Polar Surface Area: 80.92

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.58

CX Basic pKa: ┄

CX LogP: 2.43

CX LogD: 2.43

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.44

Np Likeness Score: 1.99

References

1. Sakai K, Hirose T, Iwatsuki M, Chinen T, Kimura T, Suga T, Nonaka K, Nakashima T, Sunazuka T, Usui T, Asami Y, O Mura S, Shiomi K..  (2018)  Pestynol, an Antifungal Compound Discovered Using a Saccharomyces cerevisiae 12geneΔ0HSR-iERG6-Based Assay.,  81  (7): [PMID:29975062] [10.1021/acs.jnatprod.8b00200]

2. Wang J, Liang Z, Li K, Yang B, Liu Y, Fang W, Tang L, Zhou X..  (2020)  Ene-yne Hydroquinones from a Marine-derived Strain of the Fungus Pestalotiopsis neglecta with Effects on Liver X Receptor Alpha.,  83  (4): [PMID:32283019] [10.1021/acs.jnatprod.0c00050]

Source

Source(1):

• Scientific Literature