4-(3-(4-(hydroxy(phenyl)methyl)piperidin-1-yl)propoxy)benzonitrile

ID: ALA3126179

PubChem CID: 46926612

Max Phase: Preclinical

Molecular Formula: C22H26N2O2

Molecular Weight: 350.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(OCCCN2CCC(C(O)c3ccccc3)CC2)cc1

Standard InChI:  InChI=1S/C22H26N2O2/c23-17-18-7-9-21(10-8-18)26-16-4-13-24-14-11-20(12-15-24)22(25)19-5-2-1-3-6-19/h1-3,5-10,20,22,25H,4,11-16H2

Standard InChI Key:  SYUGIOGEWUGFJR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   15.6174   -8.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8002   -8.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3903   -9.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7931   -9.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6103   -9.7491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0247   -9.0429    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5732   -9.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1691   -8.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5831   -7.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1798   -6.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3617   -6.9008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9487   -7.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3544   -8.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8419   -9.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2531   -8.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0703   -8.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4815   -7.6364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2987   -7.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7010   -8.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5174   -8.3506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9294   -7.6439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5191   -6.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7040   -6.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7463   -7.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5635   -7.6499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1600   -9.7344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  6 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 24 25  3  0
 21 24  1  0
  7 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3126179

   4-[3-[4-[Hydroxy(phenyl)methyl]piperidin-1-yl]propoxy]benzonitrile

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: 350.46

Molecular Weight (Monoisotopic): 350.1994

AlogP: 3.77

#Rotatable Bonds: 7

Polar Surface Area: 56.49

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.82

CX LogP: 3.31

CX LogD: 1.88

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.77

Np Likeness Score: -1.17

References

1. He S, Senter TJ, Pollock J, Han C, Upadhyay SK, Purohit T, Gogliotti RD, Lindsley CW, Cierpicki T, Stauffer SR, Grembecka J..  (2014)  High-affinity small-molecule inhibitors of the menin-mixed lineage leukemia (MLL) interaction closely mimic a natural protein-protein interaction.,  57  (4): [PMID:24472025] [10.1021/jm401868d]

Source

Source(1):

• Scientific Literature