6-(4-(2-Hydroxyethyl)piperazin-1-yl)-2-(3-(hydroxymethyl)-piperidin-1-yl)-4-(trifluoromethyl)nicotinonitrile

ID: ALA4085228

PubChem CID: 137648475

Max Phase: Preclinical

Molecular Formula: C19H26F3N5O2

Molecular Weight: 413.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1c(C(F)(F)F)cc(N2CCN(CCO)CC2)nc1N1CCCC(CO)C1

Standard InChI:  InChI=1S/C19H26F3N5O2/c20-19(21,22)16-10-17(26-6-4-25(5-7-26)8-9-28)24-18(15(16)11-23)27-3-1-2-14(12-27)13-29/h10,14,28-29H,1-9,12-13H2

Standard InChI Key:  XNJVLRJGPUMHDH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    3.1353  -12.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1341  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8422  -14.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5518  -13.6423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5490  -12.8197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8404  -12.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2579  -14.0490    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2572  -14.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9615  -15.2746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6710  -14.8683    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6716  -14.0502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9629  -13.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8364  -11.6029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5447  -11.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5442  -10.3798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8371   -9.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1288  -10.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1276  -11.1987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4275  -12.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7191  -12.0059    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4261  -14.0508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7187  -13.6417    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.4255  -14.8680    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.7128  -14.4536    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.4212   -9.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4216   -9.1528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3778  -15.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0864  -14.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7932  -15.2816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  1  0
  7 12  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  4  7  1  0
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  6 13  1  0
  1 19  1  0
 19 20  3  0
  2 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 17 25  1  0
 25 26  1  0
 10 27  1  0
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4085228

   ---

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: 413.44

Molecular Weight (Monoisotopic): 413.2039

AlogP: 1.30

#Rotatable Bonds: 5

Polar Surface Area: 86.86

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.18

CX LogP: 1.87

CX LogD: 1.67

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.75

Np Likeness Score: -1.59

References

1. Huard K, Ahn K, Amor P, Beebe DA, Borzilleri KA, Chrunyk BA, Coffey SB, Cong Y, Conn EL, Culp JS, Dowling MS, Gorgoglione MF, Gutierrez JA, Knafels JD, Lachapelle EA, Pandit J, Parris KD, Perez S, Pfefferkorn JA, Price DA, Raymer B, Ross TT, Shavnya A, Smith AC, Subashi TA, Tesz GJ, Thuma BA, Tu M, Weaver JD, Weng Y, Withka JM, Xing G, Magee TV..  (2017)  Discovery of Fragment-Derived Small Molecules for in Vivo Inhibition of Ketohexokinase (KHK).,  60  (18): [PMID:28853885] [10.1021/acs.jmedchem.7b00947]

Source

Source(1):

• Scientific Literature