2164U90

ID: ALA2074988

Cas Number: 152802-07-8

PubChem CID: 9841699

Max Phase: Preclinical

Molecular Formula: C21H27NO2S

Molecular Weight: 357.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC[C@]1(CC)CS(=O)(=O)c2ccccc2[C@@H](c2ccccc2)N1

Standard InChI:  InChI=1S/C21H27NO2S/c1-3-5-15-21(4-2)16-25(23,24)19-14-10-9-13-18(19)20(22-21)17-11-7-6-8-12-17/h6-14,20,22H,3-5,15-16H2,1-2H3/t20-,21-/m1/s1

Standard InChI Key:  RUWCWTXHTOBJIA-NHCUHLMSSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -6.9241    2.2766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6674    1.9186    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8510    1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3366    0.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5116    0.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9973    1.1144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1808    1.9186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1808    2.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8953    3.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8953    3.9811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6098    4.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3610    2.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1475    2.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0991   -0.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6667    0.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9682    0.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4538   -0.4216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6380   -0.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0799    2.6331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4643    1.7051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5116   -0.9596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0991   -1.6741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2741   -1.6741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8616   -0.9596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2741   -0.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  1  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  7 12  1  6
 12 13  1  0
  5 14  1  6
  3 15  2  0
  4  3  1  0
  4 18  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  2 19  2  0
  2 20  2  0
 14 21  1  0
 14 25  2  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2074988

   (3R,5R)-3-butyl-3-ethyl-5-phenyl-4,5-dihydro-2H-1lambda6,4-benzothiazepine 1,1-dioxide

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: 357.52

Molecular Weight (Monoisotopic): 357.1763

AlogP: 4.49

#Rotatable Bonds: 5

Polar Surface Area: 46.17

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.80

CX LogP: 4.77

CX LogD: 4.77

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.86

Np Likeness Score: -0.28

References

1. Hallén S, Björquist A, Ostlund-Lindqvist AM, Sachs G..  (2002)  Identification of a region of the ileal-type sodium/bile acid cotransporter interacting with a competitive bile acid transport inhibitor.,  41  (1): [PMID:12475240] [10.1021/bi0205404]

2. Bhat, B Ganesh BG and 8 more authors.  2003-09  Inhibition of ileal bile acid transport and reduced atherosclerosis in apoE-/- mice by SC-435.  [PMID:12810816]

3. Tremont, Samuel J SJ and 31 more authors.  2005-09-08  Discovery of potent, nonsystemic apical sodium-codependent bile acid transporter inhibitors (Part 1).  [PMID:16134950]

4. Wu, Yulin Y and 24 more authors.  2013-06-27  Discovery of a highly potent, nonabsorbable apical sodium-dependent bile acid transporter inhibitor (GSK2330672) for treatment of type 2 diabetes.  [PMID:23678871]

Source

Source(1):

• TP-search Transporter Database