(R/S)-3-[3-(Tert-butylamino)-2-hydroxypropoxy]-5-methyl-9Hxanthen-9-one hydrochloride

ID: ALA4128231

PubChem CID: 145963046

Max Phase: Preclinical

Molecular Formula: C21H26ClNO4

Molecular Weight: 355.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc2c(=O)c3ccc(OCC(O)CNC(C)(C)C)cc3oc12.Cl

Standard InChI:  InChI=1S/C21H25NO4.ClH/c1-13-6-5-7-17-19(24)16-9-8-15(10-18(16)26-20(13)17)25-12-14(23)11-22-21(2,3)4;/h5-10,14,22-23H,11-12H2,1-4H3;1H

Standard InChI Key:  XSRKCZPYMWRERC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   21.8336   -8.7453    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.3244   -7.4781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0389   -7.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7534   -7.4781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4679   -7.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4679   -8.7156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7534   -9.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0389   -8.7156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3244   -9.1282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6099   -8.7156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8955   -9.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1810   -8.7156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1810   -7.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8955   -7.4781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6099   -7.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3244   -6.6532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8955   -9.9532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1824   -9.1282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8968   -8.7156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6113   -9.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3258   -8.7156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6113   -9.9532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0402   -9.1282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7547   -8.7156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4692   -9.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7547   -7.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4667   -8.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  3  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 10 15  2  0
  2 15  1  0
  2 16  2  0
 11 17  1  0
 19 20  1  0
 20 21  1  0
 18 19  1  0
 20 22  1  0
 21 23  1  0
  6 18  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  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: 355.43

Molecular Weight (Monoisotopic): 355.1784

AlogP: 3.38

#Rotatable Bonds: 5

Polar Surface Area: 71.70

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.66

CX LogP: 3.37

CX LogD: 1.16

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.69

Np Likeness Score: -0.22

References

1. Kubacka M, Szkaradek N, Mogilski S, Pańczyk K, Siwek A, Gryboś A, Filipek B, Żmudzki P, Marona H, Waszkielewicz AM..  (2018)  Design, synthesis and cardiovascular evaluation of some aminoisopropanoloxy derivatives of xanthone.,  26  (13): [PMID:29706529] [10.1016/j.bmc.2018.04.038]

Source

Source(1):

• Scientific Literature