2-amino-4-(4'-butoxy-2',5'-difluorobiphenyl-4-yl)-2-(hydroxymethyl)butyl dihydrogen phosphate

ID: ALA1089558

PubChem CID: 46205132

Max Phase: Preclinical

Molecular Formula: C21H28F2NO6P

Molecular Weight: 459.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCOc1cc(F)c(-c2ccc(CCC(N)(CO)COP(=O)(O)O)cc2)cc1F

Standard InChI:  InChI=1S/C21H28F2NO6P/c1-2-3-10-29-20-12-18(22)17(11-19(20)23)16-6-4-15(5-7-16)8-9-21(24,13-25)14-30-31(26,27)28/h4-7,11-12,25H,2-3,8-10,13-14,24H2,1H3,(H2,26,27,28)

Standard InChI Key:  SPYWTTPKTMFRKZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
    3.3000    1.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.3019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250    0.3019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.5394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.3019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.3019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.3019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750    0.3019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.3019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875    1.0164    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -1.8415    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7125   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1250   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9500   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3625   -1.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1875   -1.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -0.5231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625    1.0165    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    1.0236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3604    0.1915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3597    1.8415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  1  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
 18 20  1  0
 15 21  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 22 23  1  0
 17 22  1  0
  7 11  1  0
  2  6  1  0
  2 27  1  0
  5 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1089558

   [2-Amino-4-[4-(4-butoxy-2,5-difluorophenyl)phenyl]-2-(hydroxymethyl)butyl] dihydrogen phosphate

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: 459.43

Molecular Weight (Monoisotopic): 459.1622

AlogP: 3.54

#Rotatable Bonds: 12

Polar Surface Area: 122.24

Molecular Species: ZWITTERION

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.62

CX Basic pKa: 9.84

CX LogP: 2.40

CX LogD: 1.58

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.28

Np Likeness Score: 0.20

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