(6R)-(+)-3,6-Dihydroxy-2-(hexadec-10'Z-enoyl)cyclohex-2-en-1-one

ID: ALA3289513

PubChem CID: 90681785

Max Phase: Preclinical

Molecular Formula: C22H36O4

Molecular Weight: 364.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCC/C=C\CCCCCCCCC(=O)C1=C(O)CC[C@@H](O)C1=O

Standard InChI:  InChI=1S/C22H36O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(23)21-19(24)16-17-20(25)22(21)26/h6-7,20,24-25H,2-5,8-17H2,1H3/b7-6-/t20-/m1/s1

Standard InChI Key:  URQIXKBPBUXBHD-PXDRNWIDSA-N

Molfile:  

     RDKit          2D

 26 26  0  0  0  0  0  0  0  0999 V2000
    4.6584  -13.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6584  -14.6627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3704  -15.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0825  -14.6627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0825  -13.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3704  -13.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3704  -12.5960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7963  -15.0762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3704  -15.8961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7981  -13.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5114  -13.8419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8006  -12.6023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2271  -13.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9404  -13.8461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6560  -13.4357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3693  -13.8503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0850  -13.4398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7982  -13.8544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5139  -13.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2273  -13.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0502  -13.8586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7628  -13.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4794  -13.8504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1917  -13.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9084  -13.8424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6206  -13.4260    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
  3  9  1  6
  5 10  1  0
 10 11  1  0
 10 12  2  0
 11 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  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3289513

   (4R)-2-[(Z)-hexadec-10-enoyl]-3,4-dihydroxycyclohex-2-en-1-one

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: 364.53

Molecular Weight (Monoisotopic): 364.2614

AlogP: 5.35

#Rotatable Bonds: 14

Polar Surface Area: 74.60

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.80

CX Basic pKa: ┄

CX LogP: 5.82

CX LogD: 3.27

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.25

Np Likeness Score: 1.55

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