2-amino-4-(2-fluoro-4-pentylphenyl)-2-(hydroxymethyl)butyl dihydrogen phosphate

ID: ALA1095889

PubChem CID: 46885873

Max Phase: Preclinical

Molecular Formula: C16H27FNO5P

Molecular Weight: 363.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCc1ccc(CCC(N)(CO)COP(=O)(O)O)c(F)c1

Standard InChI:  InChI=1S/C16H27FNO5P/c1-2-3-4-5-13-6-7-14(15(17)10-13)8-9-16(18,11-19)12-23-24(20,21)22/h6-7,10,19H,2-5,8-9,11-12,18H2,1H3,(H2,20,21,22)

Standard InChI Key:  SMCAMLBVPBWGKN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
   -4.2167   -1.0324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5022   -0.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7877   -1.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7877   -1.8574    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7929   -0.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5100    0.2053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0764   -0.6129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3581   -1.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6475   -0.5996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0695   -1.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7796   -0.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7724    0.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0491    0.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6581    0.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4824    0.6560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2012    0.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9113    0.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6301    0.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3402    0.6865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5152    1.0303    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5237    1.8574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6902    1.0371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3402    1.0212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3778    0.6240    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
  6 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  2  0
 14 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1095889

   2-Amino-4-(2-fluoro-4-pentylphenyl)-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: 363.37

Molecular Weight (Monoisotopic): 363.1611

AlogP: 2.29

#Rotatable Bonds: 11

Polar Surface Area: 113.01

Molecular Species: ZWITTERION

HBA: 4

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: 1.73

CX LogD: 0.92

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.35

Np Likeness Score: 0.49

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