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

ID: ALA1089564

PubChem CID: 46205452

Max Phase: Preclinical

Molecular Formula: C21H29ClNO6P

Molecular Weight: 457.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCOc1ccc(-c2ccc(CCC(N)(CO)COP(=O)(O)O)cc2)cc1Cl

Standard InChI:  InChI=1S/C21H29ClNO6P/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:  HZVGZOQMJPNOFO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   15.6802   -6.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8552   -6.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8552   -6.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0927   -7.5856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5696   -5.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0302   -6.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6177   -6.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1427   -6.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5552   -5.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3802   -5.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7927   -6.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3802   -6.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5552   -6.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3177   -6.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9052   -6.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0802   -6.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6677   -6.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0802   -5.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9052   -5.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6677   -7.5856    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.8427   -6.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4302   -5.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8427   -4.7277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4302   -4.0132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8427   -3.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8552   -7.6961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5625   -4.8083    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.5583   -3.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7333   -4.8140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3917   -4.8065    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  2  0
  1  4  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1089564

   [2-Amino-4-[4-(4-butoxy-3-chlorophenyl)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: 457.89

Molecular Weight (Monoisotopic): 457.1421

AlogP: 3.92

#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: 2.72

CX LogD: 1.90

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.28

Np Likeness Score: 0.24

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