2-amino-4-(4'-butoxybiphenyl-4-yl)-2-(hydroxymethyl)butyl dihydrogen phosphate

ID: ALA1096211

PubChem CID: 46204811

Max Phase: Preclinical

Molecular Formula: C21H30NO6P

Molecular Weight: 423.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCOc1ccc(-c2ccc(CCC(N)(CO)COP(=O)(O)O)cc2)cc1

Standard InChI:  InChI=1S/C21H30NO6P/c1-2-3-14-27-20-10-8-19(9-11-20)18-6-4-17(5-7-18)12-13-21(22,15-23)16-28-29(24,25)26/h4-11,23H,2-3,12-16,22H2,1H3,(H2,24,25,26)

Standard InChI Key:  BAPITVWOROYTDM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
    2.8025    0.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2150   -0.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9295    0.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2150    1.4252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6440   -0.0036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -0.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861   -0.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -2.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861   -2.8910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -2.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -1.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861   -1.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2150   -2.8910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9295   -2.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9295   -1.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6440   -1.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6440   -0.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6275   -0.7181    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8025    2.1397    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.4617    2.8910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0687    1.7626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5363    2.5168    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
 21 22  1  0
 22 23  1  0
 23 24  1  0
 20 21  1  0
 17 20  1  0
  7 11  1  0
  2  6  1  0
  2 25  1  0
  4 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1096211

   2-Amino-4-(4''-butoxybiphenyl-4-yl)-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: 423.45

Molecular Weight (Monoisotopic): 423.1811

AlogP: 3.26

#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: 2.11

CX LogD: 1.30

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.31

Np Likeness Score: 0.45

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