1-phenoxy-3-(2-(phenylthio)propylamino)propan-2-ol oxalate

ID: ALA3277277

PubChem CID: 12439461

Max Phase: Preclinical

Molecular Formula: C20H25NO6S

Molecular Weight: 317.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(CNCC(O)COc1ccccc1)Sc1ccccc1.O=C(O)C(=O)O

Standard InChI:  InChI=1S/C18H23NO2S.C2H2O4/c1-15(22-18-10-6-3-7-11-18)12-19-13-16(20)14-21-17-8-4-2-5-9-17;3-1(4)2(5)6/h2-11,15-16,19-20H,12-14H2,1H3;(H,3,4)(H,5,6)

Standard InChI Key:  DWCDAPLMDQGVCN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   23.6500   -9.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3577   -8.6114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9423   -8.6114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6500   -9.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9423  -10.2458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3577  -10.2458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1361   -7.8749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1349   -8.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8497   -9.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5661   -8.7018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5633   -7.8713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8479   -7.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2762   -7.4562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9922   -7.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7052   -7.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4211   -7.8606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7020   -6.6257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1341   -7.4454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8500   -7.8551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5630   -7.4400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2790   -7.8498    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.9919   -7.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7063   -7.8470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4186   -7.4324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4160   -6.6066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6950   -6.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9855   -6.6138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5599   -6.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  1  4  1  0
  4  5  1  0
  4  6  2  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 20 28  1  0
M  END

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: 317.45

Molecular Weight (Monoisotopic): 317.1449

AlogP: 3.20

#Rotatable Bonds: 9

Polar Surface Area: 41.49

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.03

CX LogP: 3.38

CX LogD: 1.75

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.70

Np Likeness Score: -0.88

References

1. Tucker H, Coope JF..  (1978)  beta-Adrenergic blocking agents. 18. 1-(Aryloxy)-3-(arylthioalkylamino)propan-2-ols and 1-substituted alkylthioamino-3-(aryloxy)propan-2-ols.,  21  (8): [PMID:29123] [10.1021/jm00206a010]

Source

Source(1):

• Scientific Literature