3-Hydroxy-2-(hexadec-10'Z-enoyl)cyclohex-2-en-1-one

ID: ALA3289512

PubChem CID: 90681784

Max Phase: Preclinical

Molecular Formula: C22H36O3

Molecular Weight: 348.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCC/C=C\CCCCCCCCC(=O)C1=C(O)CCCC1=O

Standard InChI:  InChI=1S/C22H36O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(23)22-20(24)17-15-18-21(22)25/h6-7,24H,2-5,8-18H2,1H3/b7-6-

Standard InChI Key:  VQRIOCPQBFEFMK-SREVYHEPSA-N

Molfile:  

     RDKit          2D

 25 25  0  0  0  0  0  0  0  0999 V2000
    3.7805   -9.3771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7805  -10.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4858  -10.5987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1911  -10.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1911   -9.3771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4858   -8.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4858   -8.1471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8982  -10.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9000   -8.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6065   -9.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9024   -8.1534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3154   -8.9747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0219   -9.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7308   -8.9788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4373   -9.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1462   -8.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8527   -9.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5616   -8.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2682   -9.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0833   -9.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7891   -8.9850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4990   -9.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2045   -8.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9144   -9.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6199   -8.9692    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  2  0
  6  7  1  0
  4  8  2  0
  5  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3289512

   2-[(Z)-1-hydroxyhexadec-10-enylidene]cyclohexane-1,3-dione

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: 348.53

Molecular Weight (Monoisotopic): 348.2664

AlogP: 6.38

#Rotatable Bonds: 14

Polar Surface Area: 54.37

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.12

CX Basic pKa: ┄

CX LogP: 6.69

CX LogD: 4.43

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.23

Np Likeness Score: 0.98

References

1. Ferreira EA, Reigada JB, Correia MV, Young MC, Guimarães EF, Franchi GC, Nowill AE, Lago JH, Yamaguchi LF, Kato MJ..  (2014)  Antifungal and cytotoxic 2-acylcyclohexane-1,3-diones from Peperomia alata and P. trineura.,  77  (6): [PMID:24905499] [10.1021/np500130x]

Source

Source(1):

• Scientific Literature