(2R,3S,5R)-5-((S)-2-bromo-1-chloropropan-2-yl)-2-(2-bromo-1-chlorovinyl)-2-methyltetrahydrofuran-3-yl acetate

ID: ALA2271698

PubChem CID: 10993865

Max Phase: Preclinical

Molecular Formula: C12H16Br2Cl2O3

Molecular Weight: 438.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@H]1C[C@H](C(C)(Br)CCl)O[C@@]1(C)/C(Cl)=C/Br

Standard InChI:  InChI=1S/C12H16Br2Cl2O3/c1-7(17)18-10-4-9(11(2,14)6-15)19-12(10,3)8(16)5-13/h5,9-10H,4,6H2,1-3H3/b8-5-/t9-,10+,11?,12+/m1/s1

Standard InChI Key:  JKJDNZFOACWTKF-MRTQXXJCSA-N

Molfile:  

     RDKit          2D

 19 19  0  0  0  0  0  0  0  0999 V2000
    9.4401   -3.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1081   -3.6716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7763   -3.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5202   -2.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6960   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3584   -3.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5709   -2.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1470   -4.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1548   -3.5511    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.7319   -5.1461    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   11.0035   -1.7319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6554   -3.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0425   -2.8897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2578   -3.1444    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.2376   -4.1542    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    9.0626   -4.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6660   -0.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1492   -0.3104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8453   -0.8949    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
  3  6  1  0
  3  7  1  1
  6  8  2  0
  6  9  1  0
  8 10  1  0
  4 11  1  6
  1 12  1  1
 12 13  1  0
 13 14  1  0
 12 15  1  0
 12 16  1  0
 11 17  1  0
 17 18  2  0
 17 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2271698

   [(2R,3S,5R)-2-[(Z)-2-bromo-1-chloroethenyl]-5-(2-bromo-1-chloropropan-2-yl)-2-methyloxolan-3-yl] acetate

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: 438.97

Molecular Weight (Monoisotopic): 435.8843

AlogP: 4.33

#Rotatable Bonds: 4

Polar Surface Area: 35.53

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.53

CX LogD: 3.53

Aromatic Rings: ┄

Heavy Atoms: 19

QED Weighted: 0.48

Np Likeness Score: 1.42

References

1. Argandoña VH, Rovirosa J, San-Martín A, Riquelme A, Díaz-Marrero AR, Cueto M, Darias J, Santana O, Guadaño A, González-Coloma A..  (2002)  Antifeedant effects of marine halogenated monoterpenes.,  50  (24): [PMID:12428955] [10.1021/jf025857p]

Source

Source(1):

• Scientific Literature