N-Adamantan-1-ylmethyl-5-[3-((R)-2-hydroxy-1-methyl-ethylamino)-propyl]-2-methyl-benzamide

ID: ALA4088943

PubChem CID: 137642766

Max Phase: Preclinical

Molecular Formula: C25H38N2O2

Molecular Weight: 398.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(CCCN[C@H](C)CO)cc1C(=O)NCC12CC3CC(CC(C3)C1)C2

Standard InChI:  InChI=1S/C25H38N2O2/c1-17-5-6-19(4-3-7-26-18(2)15-28)11-23(17)24(29)27-16-25-12-20-8-21(13-25)10-22(9-20)14-25/h5-6,11,18,20-22,26,28H,3-4,7-10,12-16H2,1-2H3,(H,27,29)/t18-,20?,21?,22?,25?/m1/s1

Standard InChI Key:  VKEJEPXFDMHETM-NCJOGADSSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   36.7026   -9.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5505   -8.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7736   -8.3044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1533   -8.8452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.1666   -8.0359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.9434   -8.3038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5638   -7.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3406   -8.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9610   -7.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8041   -6.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4320   -6.1520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2093   -6.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3631   -7.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7426   -7.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8332   -5.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2826   -5.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9034   -4.8107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.5081   -5.0714    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.3544   -4.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5799   -3.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9927   -4.7352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1774   -4.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3048   -4.6559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9974   -3.9168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7680   -4.1936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9974   -3.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7772   -2.7725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1774   -3.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5799   -3.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 11 10  1  0
 12 11  2  0
 13 12  1  0
 14 13  2  0
  9 14  1  0
 12 15  1  0
 11 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 22 21  1  0
 23 22  1  0
 24 23  1  0
 25 24  1  0
 20 25  1  0
 24 26  1  0
 27 26  1  0
 28 27  1  0
 22 28  1  0
 27 29  1  0
 20 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4088943

   ---

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: 398.59

Molecular Weight (Monoisotopic): 398.2933

AlogP: 3.84

#Rotatable Bonds: 9

Polar Surface Area: 61.36

Molecular Species: BASE

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.81

CX LogP: 4.00

CX LogD: 1.65

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.55

Np Likeness Score: -0.64

References

1. Warner DJ, Chen H, Cantin LD, Kenna JG, Stahl S, Walker CL, Noeske T..  (2012)  Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.,  40  (12): [PMID:22961681] [10.1124/dmd.112.047068]

Source

Source(1):

• Scientific Literature