3-O-octyl-sn-glycerol

ID: ALA1213658

PubChem CID: 446473

Max Phase: Preclinical

Molecular Formula: C11H24O3

Molecular Weight: 204.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCOC[C@H](O)CO

Standard InChI:  InChI=1S/C11H24O3/c1-2-3-4-5-6-7-8-14-10-11(13)9-12/h11-13H,2-10H2,1H3/t11-/m1/s1

Standard InChI Key:  GUPXYSSGJWIURR-LLVKDONJSA-N

Molfile:  

     RDKit          2D

 14 13  0  0  0  0  0  0  0  0999 V2000
   -2.8583   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8583    0.6208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2875   -0.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4292   -0.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5750   -0.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1458   -0.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7167   -0.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5708   -0.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8542   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1417   -0.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7125   -0.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2833   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1
  3  5  1  0
  4  6  1  0
  5  1  1  0
  6  1  1  0
  7  4  1  0
  8  7  1  0
  9 10  1  0
 10 11  1  0
 11 13  1  0
 12  8  1  0
 13 12  1  0
 14  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1213658

   (2R)-3-octoxypropane-1,2-diol

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: 204.31

Molecular Weight (Monoisotopic): 204.1725

AlogP: 1.72

#Rotatable Bonds: 10

Polar Surface Area: 49.69

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.64

CX Basic pKa: ┄

CX LogP: 1.91

CX LogD: 1.91

Aromatic Rings: ┄

Heavy Atoms: 14

QED Weighted: 0.53

Np Likeness Score: 0.63

References

1. Skinner MC, Kiselev AO, Isaacs CE, Mietzner TA, Montelaro RC, Lampe MF..  (2010)  Evaluation of WLBU2 peptide and 3-O-octyl-sn-glycerol lipid as active ingredients for a topical microbicide formulation targeting Chlamydia trachomatis.,  54  (2): [PMID:20008784] [10.1128/aac.00635-09]

2. Moncla BJ, Pryke K, Isaacs CE..  (2008)  Killing of Neisseria gonorrhoeae, Streptococcus agalactiae (group B streptococcus), Haemophilus ducreyi, and vaginal Lactobacillus by 3-O-octyl-sn-glycerol.,  52  (4): [PMID:18227178] [10.1128/aac.01023-07]

Source

Source(1):

• Scientific Literature