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2-(Cyclohexylmethoxy)-ethyl-N-[(S)-2-oxoazetidin-3-yl]-carbamate

ID: ALA3770450

PubChem CID: 86280724

Max Phase: Preclinical

Molecular Formula: C13H22N2O4

Molecular Weight: 270.33

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  O=C(N[C@H]1CNC1=O)OCCOCC1CCCCC1

Standard InChI:  InChI=1S/C13H22N2O4/c16-12-11(8-14-12)15-13(17)19-7-6-18-9-10-4-2-1-3-5-10/h10-11H,1-9H2,(H,14,16)(H,15,17)/t11-/m0/s1

Standard InChI Key:  ZACHEXOCLFQUCP-NSHDSACASA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
    5.1873   -7.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4855   -8.2648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1470   -8.1099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894   -6.0109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4761  -11.8353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4191  -10.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4833   -9.7656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5404  -10.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2193  -10.7517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  1  4  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  5  8  1  0
  6  9  2  0
  7  2  1  1
 10 11  1  0
 12 13  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 14 19  1  0
 13 14  1  0
 11 12  1  0
  4 10  1  0
M  END

Associated Targets(Human)

NAAA Tchem N-acylsphingosine-amidohydrolase (450 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Calculated Properties

Molecular Weight: 270.33Molecular Weight (Monoisotopic): 270.1580AlogP: 0.81#Rotatable Bonds: 6
Polar Surface Area: 76.66Molecular Species: NEUTRALHBA: 4HBD: 2
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 13.14CX Basic pKa: CX LogP: 0.82CX LogD: 0.82
Aromatic Rings: Heavy Atoms: 19QED Weighted: 0.55Np Likeness Score: -0.36

References

1. Nuzzi A, Fiasella A, Ortega JA, Pagliuca C, Ponzano S, Pizzirani D, Bertozzi SM, Ottonello G, Tarozzo G, Reggiani A, Bandiera T, Bertozzi F, Piomelli D..  (2016)  Potent α-amino-β-lactam carbamic acid ester as NAAA inhibitors. Synthesis and structure-activity relationship (SAR) studies.,  111  [PMID:26866968] [10.1016/j.ejmech.2016.01.046]

Source