2-Amino-4-(4'-butoxy-3'-fluorobiphenyl-4-yl)-2-(phosphoryloxymethyl)butanol

ID: ALA1091630

PubChem CID: 11647892

Max Phase: Preclinical

Molecular Formula: C21H29FNO6P

Molecular Weight: 441.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCOc1ccc(-c2ccc(CCC(N)(CO)COP(=O)(O)O)cc2)cc1F

Standard InChI:  InChI=1S/C21H29FNO6P/c1-2-3-12-28-20-9-8-18(13-19(20)22)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)

Standard InChI Key:  ULMHODUJXJVNJF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.4719   -6.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6469   -6.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6469   -5.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8844   -7.1023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3613   -5.1503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8219   -6.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4094   -5.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0656   -5.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6531   -4.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1719   -4.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5844   -5.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1719   -6.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8906   -5.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3031   -6.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1281   -6.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5406   -5.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1281   -4.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3031   -4.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5406   -7.1023    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3656   -5.6734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7781   -4.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3656   -4.2444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7781   -3.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3656   -2.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6469   -7.2128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542   -4.3250    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.3500   -3.4958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1833   -4.3250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5250   -4.3208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
 16 20  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 21 22  1  0
 17 21  1  0
  7 11  1  0
  2  6  1  0
  2 26  1  0
  5 27  1  0
  1  2  1  0
 27 28  1  0
  2  3  1  0
 27 29  1  0
  1  4  1  0
 27 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1091630

   2-Amino-4-(4''-butoxy-3''-fluorobiphenyl-4-yl)-2-(phosphoryloxymethyl)butanol

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: 0.11

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