(S)-{4-[2-(2-Hydroxy-3-phenoxy-propylamino)-ethoxy]-phenoxy}-acetic acid methyl ester, 1/4 H2O

ID: ALA1907966

PubChem CID: 15034337

Max Phase: Preclinical

Molecular Formula: C20H25NO6

Molecular Weight: 375.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)COc1ccc(OCCNC[C@H](O)COc2ccccc2)cc1

Standard InChI:  InChI=1S/C20H25NO6/c1-24-20(23)15-27-19-9-7-18(8-10-19)25-12-11-21-13-16(22)14-26-17-5-3-2-4-6-17/h2-10,16,21-22H,11-15H2,1H3/t16-/m0/s1

Standard InChI Key:  XPXQYIOOPXUJDD-INIZCTEOSA-N

Molfile:  

     RDKit          2D

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    8.1782   -0.2918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7569   -1.1171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1212   -2.4427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7527   -0.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0441   -1.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3043   -2.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185   -2.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4002   -2.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7382   -2.4177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4571    0.9462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8340   -2.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0441   -2.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3271   -1.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3313   -2.7886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6143   -1.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2918   -1.6048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9015   -2.8053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0296   -2.8386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4552   -2.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1679   -2.4009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1699    1.3713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5468   -2.4760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8132   -3.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2596   -2.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5135   -4.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2346   -3.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4163   -2.0285    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  5  1  0
  4  9  1  0
  5  1  1  0
  6  3  1  0
  7 19  1  0
  8 16  1  0
  9  7  1  0
 10 20  1  0
 11  1  1  0
 12  4  1  0
 13  6  2  0
 14  6  1  0
 15 13  1  0
 16 14  2  0
  7 17  1  1
 18  8  1  0
 19 10  1  0
 20 21  1  0
 21 18  1  0
 22 11  1  0
 23 12  2  0
 24 12  1  0
 25 23  1  0
 26 24  2  0
 27 26  1  0
  8 15  2  0
 25 27  2  0
  7 28  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1907966

   methyl 2-[4-[2-[[(2S)-2-hydroxy-3-phenoxypropyl]amino]ethoxy]phenoxy]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: 375.42

Molecular Weight (Monoisotopic): 375.1682

AlogP: 1.65

#Rotatable Bonds: 12

Polar Surface Area: 86.25

Molecular Species: BASE

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.79

CX LogP: 1.93

CX LogD: 0.53

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.43

Np Likeness Score: -0.64

References

1. Howe R, Rao BS, Holloway BR, Stribling D..  (1992)  Selective beta 3-adrenergic agonists of brown adipose tissue and thermogenesis. 1. [4-[2-[(2-Hydroxy-3-phenoxypropyl)amino]ethoxy]phenoxy]acetates.,  35  (10): [PMID:1350309] [10.1021/jm00088a009]

Source

Source(1):

• Scientific Literature