rac-(3R,5S)-5-((2-((2-phenylpyrimidin-5-yl)methylene)hydrazinyl)methyl)piperidine-3-carboxylic acid

ID: ALA4475418

PubChem CID: 155537714

Max Phase: Preclinical

Molecular Formula: C18H21N5O2

Molecular Weight: 339.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H]1CNC[C@@H](CN/N=C/c2cnc(-c3ccccc3)nc2)C1

Standard InChI:  InChI=1S/C18H21N5O2/c24-18(25)16-6-13(7-19-12-16)10-22-23-11-14-8-20-17(21-9-14)15-4-2-1-3-5-15/h1-5,8-9,11,13,16,19,22H,6-7,10,12H2,(H,24,25)/b23-11+/t13-,16+/m0/s1

Standard InChI Key:  XIAZMUAHIPFDTR-WTLQDBDKSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    4.7512  -11.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4646  -12.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1134  -11.7465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8342  -12.1480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5423  -11.7247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2630  -12.1262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2710  -12.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9875  -13.3524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6981  -12.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6875  -12.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9662  -11.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3970  -11.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1163  -12.0897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3872  -10.8607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0381  -12.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7434  -10.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0233  -10.4816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3094  -10.9062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3208  -11.7303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5895  -10.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5831   -9.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8640   -9.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1541   -9.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1680  -10.5289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8876  -10.9280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  6  5  1  1
  6  7  1  0
  6 11  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  1
 12 13  1  0
 12 14  2  0
 15  1  2  0
  1 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 15  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4475418

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 339.40

Molecular Weight (Monoisotopic): 339.1695

AlogP: 1.38

#Rotatable Bonds: 6

Polar Surface Area: 99.50

Molecular Species: ZWITTERION

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.08

CX Basic pKa: 10.06

CX LogP: -0.85

CX LogD: -0.85

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.54

Np Likeness Score: -0.90

References

1. Hauke TJ, Wein T, Höfner G, Wanner KT..  (2018)  Novel Allosteric Ligands of γ-Aminobutyric Acid Transporter 1 (GAT1) by MS Based Screening of Pseudostatic Hydrazone Libraries.,  61  (22): [PMID:30376325] [10.1021/acs.jmedchem.8b01602]

Source

Source(1):

• Scientific Literature