2-Amino-4-(2'-fluoro-4'-phenylthiobiphenyl-4-yl)-2-(phosphoryloxymethyl)butanol

ID: ALA1092286

PubChem CID: 46206105

Max Phase: Preclinical

Molecular Formula: C23H25FNO5PS

Molecular Weight: 477.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(CO)(CCc1ccc(-c2ccc(Sc3ccccc3)cc2F)cc1)COP(=O)(O)O

Standard InChI:  InChI=1S/C23H25FNO5PS/c24-22-14-20(32-19-4-2-1-3-5-19)10-11-21(22)18-8-6-17(7-9-18)12-13-23(25,15-26)16-30-31(27,28)29/h1-11,14,26H,12-13,15-16,25H2,(H2,27,28,29)

Standard InChI Key:  ARGUPDFFGZRWBD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   16.6944   -2.1664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6944   -2.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5194   -2.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4089   -1.7539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9319   -3.7059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8694   -2.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4569   -2.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9819   -2.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3944   -1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2194   -1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6319   -2.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2194   -2.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3944   -2.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1569   -2.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7444   -2.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9194   -2.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5069   -2.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9194   -1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7444   -1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6819   -2.2770    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.2694   -1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4444   -1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0319   -0.8480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4444   -0.1336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2694   -0.1336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6819   -0.8480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1569   -3.7059    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.6944   -3.8164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4042   -0.9208    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.4000   -0.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5708   -0.9253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2375   -0.9166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  5  1  0
  6  7  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  8 13  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 14 19  2  0
  8 14  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 21 26  2  0
 20 21  1  0
 17 20  1  0
 15 27  1  0
  7 11  1  0
  2  6  1  0
  2 28  1  0
  4 29  1  0
  1  2  1  0
 29 30  1  0
  2  3  1  0
 29 31  1  0
  1  4  1  0
 29 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1092286

   2-Amino-4-(2''-fluoro-4''-phenylthiobiphenyl-4-yl)-2-(phosphoryloxymethyl)butanol

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: 477.49

Molecular Weight (Monoisotopic): 477.1175

AlogP: 4.38

#Rotatable Bonds: 10

Polar Surface Area: 113.01

Molecular Species: ZWITTERION

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.62

CX Basic pKa: 9.84

CX LogP: 3.28

CX LogD: 2.46

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.32

Np Likeness Score: 0.00

References

1. Hamada M, Nakamura M, Kiuchi M, Marukawa K, Tomatsu A, Shimano K, Sato N, Sugahara K, Asayama M, Takagi K, Adachi K..  (2010)  Removal of sphingosine 1-phosphate receptor-3 (S1P(3)) agonism is essential, but inadequate to obtain immunomodulating 2-aminopropane-1,3-diol S1P(1) agonists with reduced effect on heart rate.,  53  (8): [PMID:20337461] [10.1021/jm901776q]

Source

Source(1):

• Scientific Literature