3-Hydroxy-4-methylene-2-(n-eicos-11'-yn-19'-enyl)but-2-enolide

ID: ALA4464299

PubChem CID: 155530561

Max Phase: Preclinical

Molecular Formula: C25H38O3

Molecular Weight: 386.58

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CCCCCCCC#CCCCCCCCCCCC1=C(O)C(=C)OC1=O

Standard InChI:  InChI=1S/C25H38O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-23-24(26)22(2)28-25(23)27/h3,26H,1-2,4-9,12-21H2

Standard InChI Key:  LXFGLBCGRKKMRK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    3.4323   -8.5813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1780   -7.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3608   -7.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1064   -8.5813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2092   -8.8350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3296   -8.8350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8807   -7.1392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6580   -7.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4708   -7.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -6.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7636   -6.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2437   -5.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0564   -6.0719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5365   -5.4110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3493   -5.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8295   -4.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.1225   -4.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6048   -3.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0887   -2.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9009   -3.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3849   -2.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1971   -2.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6810   -1.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4933   -1.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9772   -1.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7894   -1.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 24 25  1  0
  5  7  2  0
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  2  6  2  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4464299

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 386.58

Molecular Weight (Monoisotopic): 386.2821

AlogP: 7.30

#Rotatable Bonds: 16

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.10

CX Basic pKa: ┄

CX LogP: 8.21

CX LogD: 7.73

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.13

Np Likeness Score: 1.48

References

1. Oliveira EA, Brito IA, Lima ML, Romanelli M, Moreira-Filho JT, Neves BJ, Andrade CH, Sartorelli P, Tempone AG, Tempone AG, Costa-Silva TA, Lago JHG..  (2019)  Antitrypanosomal Activity of Acetogenins Isolated from the Seeds of Porcelia macrocarpa Is Associated with Alterations in Both Plasma Membrane Electric Potential and Mitochondrial Membrane Potential.,  82  (5): [PMID:31046273] [10.1021/acs.jnatprod.8b00890]

Source

Source(1):

• Scientific Literature