Octadecanoic acid (S)-3-[((S)-2-amino-2-carboxy-ethoxy)-hydroxy-phosphoryloxy]-2-hydroxy-propyl ester

ID: ALA585320

PubChem CID: 44474572

Max Phase: Preclinical

Molecular Formula: C24H48NO9P

Molecular Weight: 525.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCCCC(=O)OC[C@H](O)COP(=O)(O)OC[C@H](N)C(=O)O

Standard InChI:  InChI=1S/C24H48NO9P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(27)32-18-21(26)19-33-35(30,31)34-20-22(25)24(28)29/h21-22,26H,2-20,25H2,1H3,(H,28,29)(H,30,31)/t21-,22-/m0/s1

Standard InChI Key:  ZPDQFUYPBVXUKS-VXKWHMMOSA-N

Molfile:  

     RDKit          2D

 35 34  0  0  0  0  0  0  0  0999 V2000
   -3.3444    1.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6284    1.5240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9126    1.1106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966    1.5240    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4806    1.1106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7891    2.2463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6158    2.2463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2354    1.5240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9513    1.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0604    1.5240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3444    0.2839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0604    2.3507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7763    1.1106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6672    1.5240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3832    1.1106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0991    1.5240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0991    2.3507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8121    1.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5261    1.5324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2400    1.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9540    1.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6680    1.1273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3820    1.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0959    1.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8099    1.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5239    1.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2379    1.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9519    1.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6658    1.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3798    1.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0938    1.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8078    1.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5217    1.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2357    1.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9513    0.2839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 16 18  1  0
  4  5  1  0
 18 19  1  0
  1 10  1  0
 19 20  1  0
  2  3  1  0
 20 21  1  0
  1 11  1  6
 21 22  1  0
  4  6  1  0
 22 23  1  0
 10 12  2  0
 23 24  1  0
  1  2  1  0
 24 25  1  0
 10 13  1  0
 25 26  1  0
  4  7  2  0
 26 27  1  0
  9 14  1  0
 27 28  1  0
  3  4  1  0
 28 29  1  0
 14 15  1  0
 29 30  1  0
  5  8  1  0
 30 31  1  0
 15 16  1  0
 31 32  1  0
 32 33  1  0
 16 17  2  0
 33 34  1  0
  8  9  1  0
  9 35  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA585320

   (2S)-2-amino-3-[hydroxy-[(2S)-2-hydroxy-3-octadecanoyloxypropoxy]phosphoryl]oxypropanoic acid

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: 525.62

Molecular Weight (Monoisotopic): 525.3067

AlogP: 4.70

#Rotatable Bonds: 25

Polar Surface Area: 165.61

Molecular Species: ZWITTERION

HBA: 8

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.51

CX Basic pKa: 9.38

CX LogP: 3.50

CX LogD: 0.48

Aromatic Rings: ┄

Heavy Atoms: 35

QED Weighted: 0.07

Np Likeness Score: 0.78

References

1. Iwashita M, Makide K, Nonomura T, Misumi Y, Otani Y, Ishida M, Taguchi R, Tsujimoto M, Aoki J, Arai H, Ohwada T..  (2009)  Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative.,  52  (19): [PMID:19743861] [10.1021/jm900598m]

Source

Source(1):

• Scientific Literature