(S)-2-amino-3-(4-(2-(biphenyl-4-yl)ethoxy)-3-cyanophenylamino)-2-methyl-3-oxopropyl dihydrogen phosphate

ID: ALA1088819

PubChem CID: 46885742

Max Phase: Preclinical

Molecular Formula: C25H26N3O6P

Molecular Weight: 495.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@](N)(COP(=O)(O)O)C(=O)Nc1ccc(OCCc2ccc(-c3ccccc3)cc2)c(C#N)c1

Standard InChI:  InChI=1S/C25H26N3O6P/c1-25(27,17-34-35(30,31)32)24(29)28-22-11-12-23(21(15-22)16-26)33-14-13-18-7-9-20(10-8-18)19-5-3-2-4-6-19/h2-12,15H,13-14,17,27H2,1H3,(H,28,29)(H2,30,31,32)/t25-/m0/s1

Standard InChI Key:  YIQNROYJCYQWIM-VWLOTQADSA-N

Molfile:  

     RDKit          2D

 35 37  0  0  0  0  0  0  0  0999 V2000
   16.1569  -19.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1557  -20.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8706  -20.7985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5870  -20.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5841  -19.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8688  -19.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2971  -19.1395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0131  -19.5493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7260  -19.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0162  -20.3743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4420  -19.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1549  -19.1287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1375  -18.5458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3083  -18.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4409  -20.7976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7268  -20.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0120  -20.7965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2979  -20.3834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3033  -19.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5900  -19.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8742  -19.5564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8762  -20.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5901  -20.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1580  -19.1469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1589  -18.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4451  -17.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7368  -18.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7337  -19.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4474  -19.5593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8709  -19.5385    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   22.5839  -19.1233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8740  -20.3635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6544  -18.7424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4429  -19.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7283  -18.7341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
  4  5  1  0
 19 20  1  0
  8 10  2  0
 20 21  2  0
  2  3  1  0
 21 22  1  0
  9 11  1  0
 22 23  2  0
 23 18  1  0
  5  6  2  0
 11 12  1  0
 24 25  2  0
  6  1  1  0
 25 26  1  0
  9 13  1  1
 26 27  2  0
  1  2  2  0
 27 28  1  0
  9 14  1  0
 28 29  2  0
 29 24  1  0
 21 24  1  0
  5  7  1  0
 12 30  1  0
  2 15  1  0
 30 31  2  0
  3  4  2  0
 30 32  1  0
 15 16  1  0
 30 33  1  0
  7  8  1  0
 16 17  1  0
 34 35  3  0
  1 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1088819

   (S)-2-amino-3-(4-(2-(biphenyl-4-yl)ethoxy)-3-cyanophenylamino)-2-methyl-3-oxopropyl 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: 495.47

Molecular Weight (Monoisotopic): 495.1559

AlogP: 3.61

#Rotatable Bonds: 10

Polar Surface Area: 154.90

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.48

CX Basic pKa: 8.41

CX LogP: 2.46

CX LogD: 1.49

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.31

Np Likeness Score: -0.55

References

1. Evindar G, Bernier SG, Doyle E, Kavarana MJ, Satz AL, Lorusso J, Blanchette HS, Saha AK, Hannig G, Morgan BA, Westlin WF..  (2010)  Exploration of amino alcohol derivatives as novel, potent, and highly selective sphingosine-1-phosphate receptor subtype-1 agonists.,  20  (8): [PMID:20304639] [10.1016/j.bmcl.2010.02.098]

Source

Source(1):

• Scientific Literature