rac-(3R,5S)-{5-[(E)-2-[(2-{[1,1'-Biphenyl]-4-yl}phenyl)methylidene]hydrazin-1-yl]piperidine-3-carboxylic acid}

ID: ALA4548691

PubChem CID: 155549186

Max Phase: Preclinical

Molecular Formula: C25H25N3O2

Molecular Weight: 399.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H]1CNC[C@@H](N/N=C/c2ccccc2-c2ccc(-c3ccccc3)cc2)C1

Standard InChI:  InChI=1S/C25H25N3O2/c29-25(30)22-14-23(17-26-15-22)28-27-16-21-8-4-5-9-24(21)20-12-10-19(11-13-20)18-6-2-1-3-7-18/h1-13,16,22-23,26,28H,14-15,17H2,(H,29,30)/b27-16+/t22-,23+/m1/s1

Standard InChI Key:  HUJFQLHFKOTVSD-GSTCZNPNSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   41.4482   -7.0649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7338   -7.4819    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.0169   -7.0691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.3023   -7.4862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5854   -7.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5872   -6.2484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8712   -5.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1557   -6.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1607   -7.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8774   -7.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8839   -8.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1698   -8.7304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1757   -9.5554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8951   -9.9657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6100   -9.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6005   -8.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9042  -10.7899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1906  -11.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1977  -12.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9176  -12.4408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6319  -12.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6213  -11.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1584   -7.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8707   -7.0662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.8726   -6.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1559   -5.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4414   -6.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1563   -5.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8722   -4.5888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.4448   -4.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 10 11  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 14 17  1  0
  1 23  1  0
  1 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  1
 28 29  2  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4548691

   ---

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: 399.49

Molecular Weight (Monoisotopic): 399.1947

AlogP: 4.01

#Rotatable Bonds: 6

Polar Surface Area: 73.72

Molecular Species: ZWITTERION

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.64

CX Basic pKa: 8.99

CX LogP: 1.93

CX LogD: 1.92

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.43

Np Likeness Score: -0.26

References

1. Hauke TJ, Höfner G, Wanner KT..  (2019)  Generation and screening of pseudostatic hydrazone libraries derived from 5-substituted nipecotic acid derivatives at the GABA transporter mGAT4.,  27  (1): [PMID:30503411] [10.1016/j.bmc.2018.11.028]

Source

Source(1):

• Scientific Literature