Chrysogenester

ID: ALA4160418

PubChem CID: 139589899

Max Phase: Preclinical

Molecular Formula: C20H28O4

Molecular Weight: 332.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)CC/C(C)=C/CC/C(C)=C/Cc1cc(O)c(C)cc1O

Standard InChI:  InChI=1S/C20H28O4/c1-14(6-5-7-15(2)9-11-20(23)24-4)8-10-17-13-18(21)16(3)12-19(17)22/h7-8,12-13,21-22H,5-6,9-11H2,1-4H3/b14-8+,15-7+

Standard InChI Key:  XONZEOKWFDBLFK-DRRSQLPWSA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
    2.9991   -4.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9979   -4.8931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7060   -5.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4156   -4.8926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4128   -4.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7042   -3.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2913   -3.6651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7017   -2.8475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7058   -6.1192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1240   -5.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8311   -4.8904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5394   -5.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2465   -4.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5407   -6.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9548   -5.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6619   -4.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3702   -5.2934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0773   -4.8837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3715   -6.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7856   -5.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4927   -4.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2011   -5.2890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4914   -4.0643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9081   -4.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  6  8  1  0
  3  9  1  0
  4 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4160418

   ---

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: 332.44

Molecular Weight (Monoisotopic): 332.1988

AlogP: 4.57

#Rotatable Bonds: 8

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.75

CX Basic pKa: ┄

CX LogP: 4.98

CX LogD: 4.98

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.42

Np Likeness Score: 1.71

References

1. Liu S, Su M, Song SJ, Hong J, Chung HY, Jung JH..  (2018)  An Anti-Inflammatory PPAR-γ Agonist from the Jellyfish-Derived Fungus Penicillium chrysogenum J08NF-4.,  81  (2): [PMID:29389121] [10.1021/acs.jnatprod.7b00846]

Source

Source(1):

• Scientific Literature