Plakinic acid M

ID: ALA3809994

PubChem CID: 127043574

Max Phase: Preclinical

Molecular Formula: C26H42O4

Molecular Weight: 418.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](CCCCCCCCCc1ccccc1)C[C@]1(C)C[C@H](C)[C@H](CC(=O)O)OO1

Standard InChI:  InChI=1S/C26H42O4/c1-21(19-26(3)20-22(2)24(29-30-26)18-25(27)28)14-10-7-5-4-6-8-11-15-23-16-12-9-13-17-23/h9,12-13,16-17,21-22,24H,4-8,10-11,14-15,18-20H2,1-3H3,(H,27,28)/t21-,22+,24+,26-/m1/s1

Standard InChI Key:  GMTBZACDABXTKT-CDTXBXJGSA-N

Molfile:  

     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383   -1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5973    1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951    3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5549    3.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6331    3.6060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2696   -1.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625    0.0216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5631    1.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8627    2.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8634    3.7739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1630    4.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1636    6.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5240    2.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4632    6.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4638    8.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7634    9.0276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7640   10.5284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0636   11.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0643   12.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3621   13.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3597   15.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0594   15.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7616   15.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7640   13.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  6
  4  8  1  6
  8  9  1  0
  9 10  1  0
  9 11  2  0
  1 12  1  1
  1 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 14 19  1  6
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3809994

   ---

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: 418.62

Molecular Weight (Monoisotopic): 418.3083

AlogP: 6.97

#Rotatable Bonds: 14

Polar Surface Area: 55.76

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.52

CX Basic pKa: ┄

CX LogP: 7.94

CX LogD: 5.15

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.26

Np Likeness Score: 1.66

References

1. Jamison MT, Dalisay DS, Molinski TF..  (2016)  Peroxide Natural Products from Plakortis zyggompha and the Sponge Association Plakortis halichondrioides-Xestospongia deweerdtae: Antifungal Activity against Cryptococcus gattii.,  79  (3): [PMID:26859086] [10.1021/acs.jnatprod.5b00951]

Source

Source(1):

• Scientific Literature