(4S,5S)-4-(Hydroxymethyl)-3-methylene-5-octyldihydrofuran-2(3H)-one

ID: ALA4062216

PubChem CID: 137635038

Max Phase: Preclinical

Molecular Formula: C14H24O3

Molecular Weight: 240.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@@H](CCCCCCCC)[C@@H]1CO

Standard InChI:  InChI=1S/C14H24O3/c1-3-4-5-6-7-8-9-13-12(10-15)11(2)14(16)17-13/h12-13,15H,2-10H2,1H3/t12-,13+/m1/s1

Standard InChI Key:  LEKUFNINSKUOGD-OLZOCXBDSA-N

Molfile:  

     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
   14.6887   -3.8708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3588   -3.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1229   -2.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3033   -2.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0390   -3.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1307   -3.6714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6167   -1.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2573   -3.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8347   -1.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0206   -2.0064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6603   -3.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8785   -3.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2815   -2.7371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4997   -2.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9027   -2.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1210   -2.6551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5239   -2.0971    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
  3  7  2  0
  5  8  1  1
  4  9  1  6
  9 10  1  0
  8 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
M  END

Alternative Forms

1. Parent:

   

   ALA4062216

   ---

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: 240.34

Molecular Weight (Monoisotopic): 240.1725

AlogP: 2.83

#Rotatable Bonds: 8

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: ┄

CX Basic pKa: ┄

CX LogP: 3.41

CX LogD: 3.41

Aromatic Rings: ┄

Heavy Atoms: 17

QED Weighted: 0.40

Np Likeness Score: 2.22

References

1. Makowski K, Mir JF, Mera P, Ariza X, Asins G, Hegardt FG, Herrero L, García J, Serra D..  (2017)  (-)-UB006: A new fatty acid synthase inhibitor and cytotoxic agent without anorexic side effects.,  131  [PMID:28324785] [10.1016/j.ejmech.2017.03.012]

Source

Source(1):

• Scientific Literature