1-(3-Chloro-4-((3-(trifluoromethyl)benzyl)oxy)benzyl)-azetidine-3-carboxylic Acid

ID: ALA3741092

PubChem CID: 59451793

Max Phase: Preclinical

Molecular Formula: C19H17ClF3NO3

Molecular Weight: 399.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C1CN(Cc2ccc(OCc3cccc(C(F)(F)F)c3)c(Cl)c2)C1

Standard InChI:  InChI=1S/C19H17ClF3NO3/c20-16-7-12(8-24-9-14(10-24)18(25)26)4-5-17(16)27-11-13-2-1-3-15(6-13)19(21,22)23/h1-7,14H,8-11H2,(H,25,26)

Standard InChI Key:  BNVXTRHZRYNIIM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    2.5951   -3.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6522   -4.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5879   -5.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5309   -4.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5795   -6.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5373   -7.1631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6155   -7.1737    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
   -2.6003    1.4977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4994    0.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7985    1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7985    2.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4995    3.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2004    2.9933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4995    5.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5384    5.8447    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4601    5.8437    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4990    6.4440    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.7000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  1  4  1  0
  5  6  2  0
  5  7  1  0
  3  5  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  9 14  2  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
 17 22  2  0
 15 16  1  0
 12 15  1  0
  1  8  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 11 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3741092

   1-[[3-Chloro-4-[[3-(trifluoromethyl)phenyl]methoxy]phenyl]methyl]azetidine-3-carboxylic acid

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: 399.80

Molecular Weight (Monoisotopic): 399.0849

AlogP: 4.45

#Rotatable Bonds: 6

Polar Surface Area: 49.77

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.43

CX Basic pKa: 7.22

CX LogP: 1.76

CX LogD: 1.45

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.78

Np Likeness Score: -1.45

References

1. Hobson AD, Harris CM, van der Kam EL, Turner SC, Abibi A, Aguirre AL, Bousquet P, Kebede T, Konopacki DB, Gintant G, Kim Y, Larson K, Maull JW, Moore NS, Shi D, Shrestha A, Tang X, Zhang P, Sarris KK..  (2015)  Discovery of A-971432, An Orally Bioavailable Selective Sphingosine-1-Phosphate Receptor 5 (S1P5) Agonist for the Potential Treatment of Neurodegenerative Disorders.,  58  (23): [PMID:26509640] [10.1021/acs.jmedchem.5b00928]

Source

Source(1):

• Scientific Literature