(S)-7-(3-Hydroxy-3-methylpyrrolidin-1-yl)-5-(trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile

ID: ALA4063606

PubChem CID: 137635756

Max Phase: Preclinical

Molecular Formula: C14H13F3N4O

Molecular Weight: 310.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]1(O)CCN(c2c(C#N)c(C(F)(F)F)nc3cc[nH]c23)C1

Standard InChI:  InChI=1S/C14H13F3N4O/c1-13(22)3-5-21(7-13)11-8(6-18)12(14(15,16)17)20-9-2-4-19-10(9)11/h2,4,19,22H,3,5,7H2,1H3/t13-/m0/s1

Standard InChI Key:  KPYPGCUCWADQFY-ZDUSSCGKSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   13.0586  -10.5905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7684  -10.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7673  -10.1800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4822  -13.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4811  -14.3073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1891  -14.7162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1873  -13.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8960  -13.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9008  -14.3073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6852  -14.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1652  -13.8883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6774  -13.2253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7731  -14.7153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0657  -14.3062    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.7724  -15.5325    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.0598  -15.1180    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.7744  -13.0793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0661  -12.6704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1849  -12.2617    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8424  -11.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5876  -10.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5202  -11.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12  8  1  0
  5 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
  4 17  1  0
 17 18  3  0
  7 19  1  0
 19 20  1  0
 20 21  1  0
 21  2  1  0
  2 22  1  0
 22 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4063606

   ---

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: 310.28

Molecular Weight (Monoisotopic): 310.1041

AlogP: 2.41

#Rotatable Bonds: 1

Polar Surface Area: 75.94

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.06

CX LogP: 2.01

CX LogD: 2.01

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.85

Np Likeness Score: -0.48

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