(4R,5R)-4-Hydroxy-5-tridecyl-dihydrofuran-2(3H)-one

ID: ALA3986271

PubChem CID: 15232522

Max Phase: Preclinical

Molecular Formula: C17H32O3

Molecular Weight: 284.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCC[C@H]1OC(=O)C[C@H]1O

Standard InChI:  InChI=1S/C17H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-15(18)14-17(19)20-16/h15-16,18H,2-14H2,1H3/t15-,16-/m1/s1

Standard InChI Key:  NNXQMQBNCJBAAK-HZPDHXFCSA-N

Molfile:  

     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
    3.9291  -13.3929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7463  -13.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0006  -12.6162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3377  -12.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6789  -12.6162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2258  -14.0546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3364  -11.3169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9016  -12.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7314  -11.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9541  -11.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7838  -10.5133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3908   -9.9662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1682  -10.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7752   -9.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5525   -9.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1596   -9.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369   -9.6286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5439   -9.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3212   -9.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9283   -8.7866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  2  6  2  0
  4  7  1  6
  5  8  1  6
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 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  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3986271

   (4R,5R)-4-hydroxy-5-tridecyloxolan-2-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: 284.44

Molecular Weight (Monoisotopic): 284.2351

AlogP: 4.36

#Rotatable Bonds: 12

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.91

CX Basic pKa: ┄

CX LogP: 5.06

CX LogD: 5.06

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.43

Np Likeness Score: 1.47

References

1. Sweidan A, Chollet-Krugler M, van de Weghe P, Chokr A, Tomasi S, Bonnaure-Mallet M, Bousarghin L..  (2016)  Design, synthesis and biological evaluation of potential antibacterial butyrolactones.,  24  (22): [PMID:27687969] [10.1016/j.bmc.2016.09.040]

Source

Source(1):

• Scientific Literature