2-Amino-4-(4'-butoxy-2'-fluorobiphenyl-4-yl)-2-(phosphoryloxymethy)butanol

ID: ALA1089557

PubChem CID: 46885916

Max Phase: Preclinical

Molecular Formula: C21H30F2NO6P

Molecular Weight: 441.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCOc1ccc(-c2ccc(CCC(N)(CO)COP(=O)(O)O)cc2)c(F)c1.F

Standard InChI:  InChI=1S/C21H29FNO6P.FH/c1-2-3-12-28-18-8-9-19(20(22)13-18)17-6-4-16(5-7-17)10-11-21(23,14-24)15-29-30(25,26)27;/h4-9,13,24H,2-3,10-12,14-15,23H2,1H3,(H2,25,26,27);1H

Standard InChI Key:  FWSQKUFKMUUSSA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 31  0  0  0  0  0  0  0  0999 V2000
    2.0313   -2.9375    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    0.4244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152    0.0119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8027    0.7264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6443    0.0119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152    1.4408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5007   -0.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.0119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.2257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.0119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3572   -1.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718   -1.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718   -2.4632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2152   -2.8757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9298   -1.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6443   -1.2257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6443   -0.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6278   -0.7027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8027    2.1554    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.4005    2.8757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4755    2.6330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0955    1.7305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -2.8757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3573   -2.8757    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  4  6  1  0
  7  8  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  9 14  2  0
 15 16  1  0
 16 30  2  0
 30 17  1  0
 17 18  2  0
 18 19  1  0
 15 19  2  0
  9 15  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 20 21  1  0
 17 20  1  0
  8 12  1  0
  3  7  1  0
  3 25  1  0
  6 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  2  0
 16 31  1  0
M  END

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: 441.44

Molecular Weight (Monoisotopic): 441.1717

AlogP: 3.40

#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: 2.26

CX LogD: 1.44

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.29

Np Likeness Score: 0.19

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