methyl 2-((2R,6S)-6-(3-(2-((2S,3R)-3-butyloxiran-2-yl)ethoxy)phenyl)tetrahydro-2H-pyran-2-yl)acetate

ID: ALA28666

PubChem CID: 44277758

Max Phase: Preclinical

Molecular Formula: C22H32O5

Molecular Weight: 376.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC[C@H]1O[C@H]1CCOc1cccc([C@@H]2CCC[C@H](CC(=O)OC)O2)c1

Standard InChI:  InChI=1S/C22H32O5/c1-3-4-10-20-21(27-20)12-13-25-17-8-5-7-16(14-17)19-11-6-9-18(26-19)15-22(23)24-2/h5,7-8,14,18-21H,3-4,6,9-13,15H2,1-2H3/t18-,19+,20-,21+/m1/s1

Standard InChI Key:  ZFSKOCDOXGAWHP-MHTWAQMVSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  1  0  0  0  0  0999 V2000
   -2.0958    1.2583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6750    0.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5000    0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0417    0.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4667    0.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292    0.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4667    1.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125    0.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542    0.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8917    0.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542    1.7583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9625    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792    0.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    1.7583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2458    0.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4667    0.1083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2125    0.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125    1.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292   -0.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0417   -1.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8917    1.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542   -0.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792    1.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917    2.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9333    0.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6458    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3583    0.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  6  1  0
  9  5  1  1
  6  8  1  1
  7  5  1  0
  8 10  2  0
  9  4  1  0
 10 13  1  0
 11  7  2  0
  2 12  1  1
 13 16  1  0
 14  7  1  0
 15 12  1  0
 16 15  1  0
  3 17  1  1
 18 21  2  0
 19  6  1  0
 20 19  1  0
 21 23  1  0
 22 20  1  0
 23 13  2  0
 24 14  1  0
 25 17  1  0
 26 25  1  0
 27 26  1  0
  3  2  1  0
  8 18  1  0
 22  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA28666

   methyl 2-[(2R,6S)-6-[3-[2-[(2S,3R)-3-butyloxiran-2-yl]ethoxy]phenyl]oxan-2-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: 376.49

Molecular Weight (Monoisotopic): 376.2250

AlogP: 4.59

#Rotatable Bonds: 10

Polar Surface Area: 57.29

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.25

CX LogD: 4.25

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.44

Np Likeness Score: 0.43

References

1. Edmunds AJ, Arnold G, Hagmann L, Schaffner R, Furlenmeier H..  (2000)  Synthesis of simplified herboxidiene aromatic hybrids.,  10  (12): [PMID:10890165] [10.1016/s0960-894x(00)00230-4]

Source

Source(1):

• Scientific Literature