O-(hydroxy((R)-2-hydroxy-3-(3-(3-(undecyloxy)phenyl)propanamido)propoxy)phosphoryl)-L-serine

ID: ALA5205892

PubChem CID: 168297615

Max Phase: Preclinical

Molecular Formula: C26H45N2O9P

Molecular Weight: 560.63

Names and Identifiers

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

Standard InChI:  InChI=1S/C26H45N2O9P/c1-2-3-4-5-6-7-8-9-10-16-35-23-13-11-12-21(17-23)14-15-25(30)28-18-22(29)19-36-38(33,34)37-20-24(27)26(31)32/h11-13,17,22,24,29H,2-10,14-16,18-20,27H2,1H3,(H,28,30)(H,31,32)(H,33,34)/t22-,24+/m1/s1

Standard InChI Key:  TWRQLJUTKHZFPT-VWNXMTODSA-N

Molfile:  

 
     RDKit          2D

 38 38  0  0  0  0  0  0  0  0999 V2000
   -7.8605    0.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1459    0.0137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4313    0.4260    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7168    0.0137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0022    0.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2876    0.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2876   -0.8382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5731    0.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8585    0.0137    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1439    0.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4294    0.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7148    0.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0002    0.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7141    0.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288    0.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5726    0.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2871    0.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0016    0.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7163    0.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4307    0.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1454    0.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8600    0.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5745    0.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2891    0.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0037    0.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288   -0.8382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7141   -1.2505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0002   -0.8382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1439    1.2505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0180    1.1418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8430    1.1418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5748    0.0132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2893    0.4255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0037    0.0128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2893    1.2505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5748   -0.8116    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  6  5  1  0
  6  7  1  1
  8  6  1  0
  9  8  1  0
 10  9  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 15 14  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 28 15  1  0
 29 28  2  0
 30 29  1  0
 13 30  2  0
 31 10  2  0
  3 32  2  0
  3 33  1  0
  1 34  1  0
 34 35  1  0
 35 36  1  0
 35 37  2  0
 34 38  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA5205892

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 560.63

Molecular Weight (Monoisotopic): 560.2863

AlogP: 3.55

#Rotatable Bonds: 23

Polar Surface Area: 177.64

Molecular Species: ZWITTERION

HBA: 8

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.55

CX Basic pKa: 9.38

CX LogP: 2.00

CX LogD: -1.06

Aromatic Rings: 1

Heavy Atoms: 38

QED Weighted: 0.10

Np Likeness Score: 0.09

References

1. Sayama M, Uwamizu A, Ikubo M, Chen L, Yan G, Otani Y, Inoue A, Aoki J, Ohwada T..  (2021)  Switching Lysophosphatidylserine G Protein-Coupled Receptor Agonists to Antagonists by Acylation of the Hydrophilic Serine Amine.,  64  (14.0): [PMID:34233115] [10.1021/acs.jmedchem.1c00347]

Source

Source(1):

• Scientific Literature