(2S,3S)-2-Amino-3-(hydroxy-{(R)-2-hydroxy-3-[3-(3-undecyloxy-phenyl)-propionyloxy]-propoxy}-phosphoryloxy)-butyric acid

ID: ALA3577263

PubChem CID: 122177590

Max Phase: Preclinical

Molecular Formula: C27H46NO10P

Molecular Weight: 575.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCOc1cccc(CCC(=O)OC[C@@H](O)COP(=O)(O)O[C@@H](C)[C@H](N)C(=O)O)c1

Standard InChI:  InChI=1S/C27H46NO10P/c1-3-4-5-6-7-8-9-10-11-17-35-24-14-12-13-22(18-24)15-16-25(30)36-19-23(29)20-37-39(33,34)38-21(2)26(28)27(31)32/h12-14,18,21,23,26,29H,3-11,15-17,19-20,28H2,1-2H3,(H,31,32)(H,33,34)/t21-,23+,26-/m0/s1

Standard InChI Key:  GEYPUJKTNAJBTR-SYVJQLTCSA-N

Molfile:  

     RDKit          2D

 39 39  0  0  0  0  0  0  0  0999 V2000
    5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1873   -7.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4855   -8.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4833   -9.7656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7815  -10.5187    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.7794  -12.0195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8218   -9.9205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7838   -9.3187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0776  -12.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0755  -14.2734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3737  -15.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0352  -14.8716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9336   -3.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4140  -14.4283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3720  -16.2265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1179  -12.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1470   -8.1099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1872   -7.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4854   -8.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4833   -9.7657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7815  -10.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7793  -12.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0775  -12.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0758  -13.9727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14  1  1  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  5  8  2  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  1
 13 14  1  0
 13 15  1  0
 15 16  1  0
 17 16  1  0
 13 18  2  0
 11 19  1  0
 11 20  2  0
 17 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 17  1  0
  9 26  1  1
  2 27  1  6
 24 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3577263

   ---

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: 575.64

Molecular Weight (Monoisotopic): 575.2859

AlogP: 4.37

#Rotatable Bonds: 23

Polar Surface Area: 174.84

Molecular Species: ZWITTERION

HBA: 9

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.54

CX Basic pKa: 9.45

CX LogP: 3.16

CX LogD: 0.09

Aromatic Rings: 1

Heavy Atoms: 39

QED Weighted: 0.08

Np Likeness Score: 0.43

References

1. Ikubo M, Inoue A, Nakamura S, Jung S, Sayama M, Otani Y, Uwamizu A, Suzuki K, Kishi T, Shuto A, Ishiguro J, Okudaira M, Kano K, Makide K, Aoki J, Ohwada T..  (2015)  Structure-activity relationships of lysophosphatidylserine analogs as agonists of G-protein-coupled receptors GPR34, P2Y10, and GPR174.,  58  (10): [PMID:25970039] [10.1021/jm5020082]

Source

Source(1):

• Scientific Literature