1-phenoxy-3-(3-(phenylthio)butan-2-ylamino)propan-2-ol oxalate

ID: ALA3277276

PubChem CID: 12439459

Max Phase: Preclinical

Molecular Formula: C21H27NO6S

Molecular Weight: 331.48

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H25NO2S.C2H2O4/c1-15(16(2)23-19-11-7-4-8-12-19)20-13-17(21)14-22-18-9-5-3-6-10-18;3-1(4)2(5)6/h3-12,15-17,20-21H,13-14H2,1-2H3;(H,3,4)(H,5,6)

Standard InChI Key:  CDPMMTZGDOENKF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
   12.4929   -9.6093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2006   -9.2007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7851   -9.2007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4929  -10.4265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7851  -10.8350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2006  -10.8350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4026   -8.3249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4015   -9.1522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1163   -9.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8328   -9.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8299   -8.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1145   -7.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5428   -7.9060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2588   -8.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9717   -7.9006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6877   -8.3104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9686   -7.0756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4006   -7.8952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1166   -8.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8295   -7.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5455   -8.2996    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.2584   -7.8845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9727   -8.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6851   -7.8824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6825   -7.0565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9614   -6.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2520   -7.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1198   -9.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8264   -7.0648    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
 19 28  1  0
 20 29  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: 331.48

Molecular Weight (Monoisotopic): 331.1606

AlogP: 3.59

#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: 9.11

CX LogP: 3.80

CX LogD: 2.09

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.69

Np Likeness Score: -0.65

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