2-({[(3R,5R)-3-Butyl-3-ethyl-7-(methyloxy)-1,1-dioxido-5-phenyl-2,3,4,5-tetrahydro-1,4-benzothiazepin-8-yl]methyl}-amino)ethanesulfonic acid

ID: ALA2387399

PubChem CID: 71733736

Max Phase: Preclinical

Molecular Formula: C25H36N2O6S2

Molecular Weight: 524.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC[C@]1(CC)CS(=O)(=O)c2cc(CNCCS(=O)(=O)O)c(OC)cc2[C@@H](c2ccccc2)N1

Standard InChI:  InChI=1S/C25H36N2O6S2/c1-4-6-12-25(5-2)18-34(28,29)23-15-20(17-26-13-14-35(30,31)32)22(33-3)16-21(23)24(27-25)19-10-8-7-9-11-19/h7-11,15-16,24,26-27H,4-6,12-14,17-18H2,1-3H3,(H,30,31,32)/t24-,25-/m1/s1

Standard InChI Key:  CYDNTKYPQAZFFS-JWQCQUIFSA-N

Molfile:  

     RDKit          2D

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    1.4977   -4.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0556   -2.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9837    2.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6477    4.1419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.3862    8.4684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2194    0.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6526   -0.2516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9180   -1.4219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1198   -0.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6852   -0.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -1.5574    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4011   -2.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4925   -4.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0733   -5.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4687   -4.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8879   -3.1018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  5  4  1  1
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  2  0
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 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  2  0
 19 22  1  0
 14 23  2  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  2  0
 27 12  1  0
 27 28  1  0
 28 29  1  0
 29  5  1  0
 28 30  1  6
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2387399

   2-[[(3R,5R)-3-butyl-3-ethyl-7-methoxy-1,1-dioxo-5-phenyl-4,5-dihydro-2H-1lambda6,4-benzothiazepin-8-yl]methylamino]ethanesulfonic acid

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: 524.71

Molecular Weight (Monoisotopic): 524.2015

AlogP: 3.48

#Rotatable Bonds: 11

Polar Surface Area: 121.80

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -2.18

CX Basic pKa: 7.60

CX LogP: 1.94

CX LogD: 1.78

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.30

Np Likeness Score: -0.13

References

1. Wu Y, Aquino CJ, Cowan DJ, Anderson DL, Ambroso JL, Bishop MJ, Boros EE, Chen L, Cunningham A, Dobbins RL, Feldman PL, Harston LT, Kaldor IW, Klein R, Liang X, McIntyre MS, Merrill CL, Patterson KM, Prescott JS, Ray JS, Roller SG, Yao X, Young A, Yuen J, Collins JL..  (2013)  Discovery of a highly potent, nonabsorbable apical sodium-dependent bile acid transporter inhibitor (GSK2330672) for treatment of type 2 diabetes.,  56  (12): [PMID:23678871] [10.1021/jm400459m]

2.  (2015)  Chemical compounds, 

Source

Source(2):

• Scientific Literature
• BindingDB Database