2-Amino-4-(4'-phenoxybiphenyl-4-yl)-2-(phosphoryloxymethyl)-butanol

ID: ALA1093573

PubChem CID: 46205453

Max Phase: Preclinical

Molecular Formula: C23H26NO6P

Molecular Weight: 443.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(CO)(CCc1ccc(-c2ccc(Oc3ccccc3)cc2)cc1)COP(=O)(O)O

Standard InChI:  InChI=1S/C23H26NO6P/c24-23(16-25,17-29-31(26,27)28)15-14-18-6-8-19(9-7-18)20-10-12-22(13-11-20)30-21-4-2-1-3-5-21/h1-13,25H,14-17,24H2,(H2,26,27,28)

Standard InChI Key:  NRSOKUKPKITAQK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.3625  -19.3331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5375  -19.3331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5375  -18.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7750  -20.0476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2520  -18.0956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7125  -19.3331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3000  -18.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1750  -18.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2375  -17.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0625  -17.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7125  -17.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1250  -17.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7125  -16.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8875  -16.4753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4750  -17.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5375  -20.1581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2520  -17.2705    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.2458  -16.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0851  -17.2675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4190  -17.2817    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
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 21 26  2  0
 20 21  1  0
 17 20  1  0
  7 11  1  0
  2  6  1  0
  2 27  1  0
  5 28  1  0
  1  2  1  0
 28 29  1  0
  2  3  1  0
 28 30  2  0
  1  4  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1093573

   2-Amino-4-(4''-phenoxybiphenyl-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: 443.44

Molecular Weight (Monoisotopic): 443.1498

AlogP: 3.88

#Rotatable Bonds: 10

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: 2.45

CX LogD: 1.63

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.35

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