2-Amino-4-[2'-fluoro-4'-(4-methylphenoxy)biphenyl-4-yl]-2-(phosphoryloxymethyl)butanol

ID: ALA1092284

PubChem CID: 46886019

Max Phase: Preclinical

Molecular Formula: C24H28NO6P

Molecular Weight: 457.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(Oc2ccc(-c3ccc(CCC(N)(CO)COP(=O)(O)O)cc3)cc2)cc1

Standard InChI:  InChI=1S/C24H28NO6P/c1-18-2-10-22(11-3-18)31-23-12-8-21(9-13-23)20-6-4-19(5-7-20)14-15-24(25,16-26)17-30-32(27,28)29/h2-13,26H,14-17,25H2,1H3,(H2,27,28,29)

Standard InChI Key:  YITNXPJPZVLMFC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   10.5272   -8.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3064   -7.4319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3521   -8.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7646   -7.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2396   -7.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8271   -8.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0021   -8.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5897   -7.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0021   -6.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8271   -6.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.5359   -7.5992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5272   -7.4883    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9439   -8.3163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7688   -8.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1768   -9.0387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7596   -9.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9347   -9.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5268   -9.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1675  -10.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5272   -9.1383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8268   -9.5743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8268  -11.2243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6518  -10.3993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0018  -10.3993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8268  -10.3993    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  6 11  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 17  2  0
  6 12  1  0
 15 18  1  0
  5  9  1  0
  2  4  1  0
  2 19  1  0
  1  2  1  0
  2 27  1  0
  1  3  1  0
  4  5  1  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 20 25  2  0
  6  7  1  0
 23 26  1  0
 27 28  1  0
 28 32  1  0
 32 29  1  0
 32 30  1  0
 32 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1092284

   [2-Amino-2-(hydroxymethyl)-4-[4-[4-(4-methylphenoxy)phenyl]phenyl]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: 457.46

Molecular Weight (Monoisotopic): 457.1654

AlogP: 4.19

#Rotatable Bonds: 10

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: 2.96

CX LogD: 2.15

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.34

Np Likeness Score: 0.37

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