1-((1,3,6,7-Tetramethoxyxanthone-4-yl)-sulfonyl)-3-(N,N-diethyl-aminocarbonyl)-piperidine

ID: ALA1097385

PubChem CID: 46887487

Max Phase: Preclinical

Molecular Formula: C27H34N2O9S

Molecular Weight: 562.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)C(=O)C1CCCN(S(=O)(=O)c2c(OC)cc(OC)c3c(=O)c4cc(OC)c(OC)cc4oc23)C1

Standard InChI:  InChI=1S/C27H34N2O9S/c1-7-28(8-2)27(31)16-10-9-11-29(15-16)39(32,33)26-22(37-6)14-21(36-5)23-24(30)17-12-19(34-3)20(35-4)13-18(17)38-25(23)26/h12-14,16H,7-11,15H2,1-6H3

Standard InChI Key:  YXLGXPDXFHKMCY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 39 42  0  0  0  0  0  0  0  0999 V2000
    5.2487   -5.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8232   -4.6600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9928   -4.6770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5960   -5.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0736   -5.3554    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223   -3.9379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0472   -3.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7711   -5.4158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3444   -4.7097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8481   -6.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0206   -6.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6203   -6.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2753   -6.7972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7954   -6.8349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8705   -7.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0453   -7.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6424   -8.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0634   -8.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8917   -8.9443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2909   -8.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6609   -9.6775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8360   -9.6890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3156   -9.6520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9147  -10.3730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4980   -6.0628    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4792   -4.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6542   -4.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0975   -6.7847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5184   -7.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3437   -7.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7463   -6.7593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3236   -6.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5712   -6.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9933   -7.4571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9741   -6.0283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5904   -8.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0124   -8.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8182   -7.4461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2402   -8.1549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0
  8  9  1  0
 19 20  2  0
 20 15  1  0
 10 11  2  0
 18 21  1  0
  4 11  1  0
 21 22  1  0
  1  2  2  0
 19 23  1  0
  1  5  1  0
 23 24  1  0
 10  1  1  0
  5 25  1  0
 10 13  1  0
  5 26  2  0
 11 12  1  0
  5 27  2  0
 25 28  1  0
 12 16  1  0
 15 13  1  0
  2  6  1  0
 12 14  2  0
  2  3  1  0
 25 32  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
  6  7  1  0
 31 33  1  0
 15 16  2  0
 33 34  1  0
 33 35  2  0
 16 17  1  0
 34 36  1  0
  4  8  1  0
 36 37  1  0
 17 18  2  0
 34 38  1  0
  3  4  2  0
 38 39  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1097385

   N,N-diethyl-1-(1,3,6,7-tetramethoxy-9-oxoxanthen-4-yl)sulfonylpiperidine-3-carboxamide

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: 562.64

Molecular Weight (Monoisotopic): 562.1985

AlogP: 3.25

#Rotatable Bonds: 9

Polar Surface Area: 124.82

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.97

CX LogD: 1.97

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.36

Np Likeness Score: -0.51

References

1. Hu H, Liao H, Zhang J, Wu W, Yan J, Yan Y, Zhao Q, Zou Y, Chai X, Yu S, Wu Q..  (2010)  First identification of xanthone sulfonamides as potent acyl-CoA:cholesterol acyltransferase (ACAT) inhibitors.,  20  (10): [PMID:20403694] [10.1016/j.bmcl.2010.03.101]

2. Pokhrel, Laxman and 5 more authors.  2012-10-25  Inhibition of Acyl-CoA: cholesterol acyltransferase (ACAT), overexpression of cholesterol transporter gene, and protection of amyloid β (Aβ) oligomers-induced neuronal cell death by tricyclic pyrone molecules.  [PMID:23025824]

3. Ting, Pauline C PC and 10 more authors.  2013-02-15  Lead optimization of a pyridine-carboxamide series as DGAT-1 inhibitors.  [PMID:23317570]

4. Eguchi, Keisuke K and 10 more authors.  2013-07-01  Manzamine A, a marine-derived alkaloid, inhibits accumulation of cholesterol ester in macrophages and suppresses hyperlipidemia and atherosclerosis in vivo.  [PMID:23665143]

Source

Source(1):

• Scientific Literature