2-amino-4-(3-chloro-4'-pentylbiphenyl-4-yl)-2-(hydroxymethyl)butyl dihydrogen phosphate

ID: ALA1096210

PubChem CID: 46204808

Max Phase: Preclinical

Molecular Formula: C22H31ClNO5P

Molecular Weight: 455.92

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCc1ccc(-c2ccc(CCC(N)(CO)COP(=O)(O)O)c(Cl)c2)cc1

Standard InChI:  InChI=1S/C22H31ClNO5P/c1-2-3-4-5-17-6-8-18(9-7-17)20-11-10-19(21(23)14-20)12-13-22(24,15-25)16-29-30(26,27)28/h6-11,14,25H,2-5,12-13,15-16,24H2,1H3,(H2,26,27,28)

Standard InChI Key:  VYKOHCADRJRQNT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
   -3.1302   -1.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4158   -0.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8447   -0.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7013   -0.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9868   -0.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1566    0.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1566   -0.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4421   -0.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2724   -0.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2724    0.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4421    0.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711    0.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711    1.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5855    2.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    0.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5855    0.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    2.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289    1.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289    0.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4434    0.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4434   -0.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4421   -1.5543    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.8283   -0.0148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4158   -2.1582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033   -2.8727    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6253   -3.4147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3461   -2.3740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5908   -3.5872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  1  0
  3 26  1  0
  5  6  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  7 12  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 18  2  0
  7 13  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 16 19  1  0
  9 24  1  0
  6 10  1  0
  2  5  1  0
  2 25  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1096210

   [2-Amino-4-[2-chloro-4-(4-pentylphenyl)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: 455.92

Molecular Weight (Monoisotopic): 455.1628

AlogP: 4.47

#Rotatable Bonds: 12

Polar Surface Area: 113.01

Molecular Species: ZWITTERION

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.62

CX Basic pKa: 9.84

CX LogP: 3.84

CX LogD: 3.03

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.28

Np Likeness Score: 0.42

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