(O-(hydroxy(((3S,4R)-3-((3-(2-(undecyloxy)phenyl)propanoyl)oxy)tetrahydro-2H-pyran-4-yl)oxy)-phosphoryl)-L-serine)

ID: ALA4759297

PubChem CID: 78319667

Max Phase: Preclinical

Molecular Formula: C28H46NO10P

Molecular Weight: 587.65

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCOc1ccccc1CCC(=O)O[C@@H]1COCC[C@H]1OP(=O)(O)OC[C@H](N)C(=O)O

Standard InChI:  InChI=1S/C28H46NO10P/c1-2-3-4-5-6-7-8-9-12-18-36-24-14-11-10-13-22(24)15-16-27(30)38-26-21-35-19-17-25(26)39-40(33,34)37-20-23(29)28(31)32/h10-11,13-14,23,25-26H,2-9,12,15-21,29H2,1H3,(H,31,32)(H,33,34)/t23-,25+,26+/m0/s1

Standard InChI Key:  FTEXYKVSENDFKC-SKBVVQJISA-N

Molfile:  

 
     RDKit          2D

 40 41  0  0  0  0  0  0  0  0999 V2000
    3.9663   -1.7499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3790   -2.4598    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.7874   -1.7475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2576   -2.8726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9653   -2.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5499   -2.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8422   -2.8726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5499   -1.6468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2576   -3.6897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6730   -2.8726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0884   -2.8726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5038   -3.6897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2116   -4.0983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2116   -4.9155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9193   -3.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6270   -4.0983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3347   -3.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0425   -4.1003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7497   -3.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7502   -2.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0375   -2.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3332   -2.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0415   -4.9175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7432   -5.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4489   -4.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1547   -5.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8604   -4.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5662   -5.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2720   -4.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9777   -5.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6835   -4.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3892   -5.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0974   -4.9164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8046   -5.3258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7953   -2.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5038   -2.8726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2068   -2.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2074   -1.6482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4989   -1.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7898   -1.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  2  0
  4  9  1  6
  5 10  1  0
 10  2  1  0
  2 11  1  0
 35 11  1  6
 36 12  1  1
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 18 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 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
 35 36  1  0
 35 40  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4759297

   (2S)-2-amino-3-[hydroxy-[(3R,4R)-3-[3-(2-undecoxyphenyl)propanoyloxy]oxan-4-yl]oxyphosphoryl]oxypropanoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 587.65

Molecular Weight (Monoisotopic): 587.2859

AlogP: 4.78

#Rotatable Bonds: 21

Polar Surface Area: 163.84

Molecular Species: ZWITTERION

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.51

CX Basic pKa: 9.38

CX LogP: 3.31

CX LogD: 0.26

Aromatic Rings: 1

Heavy Atoms: 40

QED Weighted: 0.10

Np Likeness Score: 0.48

References

1. Nakamura S,Sayama M,Uwamizu A,Jung S,Ikubo M,Otani Y,Kano K,Omi J,Inoue A,Aoki J,Ohwada T.  (2020)  Non-naturally Occurring Regio Isomer of Lysophosphatidylserine Exhibits Potent Agonistic Activity toward G Protein-Coupled Receptors.,  63  (17): [PMID:32787112] [10.1021/acs.jmedchem.0c01126]

Source

Source(1):

• Scientific Literature