2-Amino-4-(4'-benzyloxy-2'-fluorobiphenyl-4-yl)-2-(phosphoryloxymethyl)butanol

ID: ALA1092272

PubChem CID: 46205775

Max Phase: Preclinical

Molecular Formula: C24H27FNO6P

Molecular Weight: 475.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(CO)(CCc1ccc(-c2ccc(OCc3ccccc3)cc2F)cc1)COP(=O)(O)O

Standard InChI:  InChI=1S/C24H27FNO6P/c25-23-14-21(31-15-19-4-2-1-3-5-19)10-11-22(23)20-8-6-18(7-9-20)12-13-24(26,16-27)17-32-33(28,29)30/h1-11,14,27H,12-13,15-17,26H2,(H2,28,29,30)

Standard InChI Key:  UISRQTRAIGWARZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   10.0896  -23.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0896  -24.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8688  -23.0966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   13.8020  -23.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.1521  -23.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5645  -22.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.6270  -21.8345    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.1020  -23.2635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5146  -23.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3396  -23.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7520  -23.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5771  -23.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9895  -23.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5771  -24.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7520  -24.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0896  -23.1530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3708  -26.0375    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.3667  -26.8583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5500  -26.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1917  -26.0429    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
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 12 13  1  0
  8 13  2  0
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 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 14 19  2  0
  8 14  1  0
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 22 23  1  0
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 27 28  1  0
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 21 22  1  0
 17 21  1  0
  7 11  1  0
  2  6  1  0
  2 29  1  0
  5 30  1  0
  1  2  1  0
 30 31  1  0
  2  3  1  0
 30 32  1  0
  1  4  1  0
 30 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1092272

   [2-Amino-4-[4-(2-fluoro-4-phenylmethoxyphenyl)phenyl]-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: 475.45

Molecular Weight (Monoisotopic): 475.1560

AlogP: 3.80

#Rotatable Bonds: 11

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: 2.66

CX LogD: 1.84

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.31

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