rac-(3R,5S)-5-((2-((3-(1H-pyrrol-1-yl)thiophen-2-yl)methylene)hydrazinyl)methyl)piperidine-3-carboxylic acid

ID: ALA4476853

PubChem CID: 155538575

Max Phase: Preclinical

Molecular Formula: C16H20N4O2S

Molecular Weight: 332.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H]1CNC[C@@H](CN/N=C/c2sccc2-n2cccc2)C1

Standard InChI:  InChI=1S/C16H20N4O2S/c21-16(22)13-7-12(8-17-10-13)9-18-19-11-15-14(3-6-23-15)20-4-1-2-5-20/h1-6,11-13,17-18H,7-10H2,(H,21,22)/b19-11+/t12-,13+/m0/s1

Standard InChI Key:  CYYKRNAWGSMWQR-SVRLCZNKSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    2.1985  -15.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8660  -16.3227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4802  -16.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1939  -16.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0205  -15.6528    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9483  -16.7933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6147  -16.3070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3350  -16.7087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0431  -16.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7638  -16.6869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7718  -17.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4884  -17.9130    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1989  -17.4931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1883  -16.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4671  -16.2613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8978  -16.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6171  -16.6504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8880  -15.4215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3957  -17.6941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6835  -18.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8567  -18.9172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6775  -19.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0114  -18.2474    0.0000 C   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  1  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
 10  9  1  1
 10 11  1  0
 10 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  1
 16 17  1  0
 16 18  2  0
  3 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476853

   ---

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: 332.43

Molecular Weight (Monoisotopic): 332.1307

AlogP: 1.77

#Rotatable Bonds: 6

Polar Surface Area: 78.65

Molecular Species: ZWITTERION

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.36

CX Basic pKa: 10.06

CX LogP: -0.45

CX LogD: -0.45

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.56

Np Likeness Score: -1.33

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