(O-(Hydroxy(((S)-1-methoxy-3-(oleoyloxy)-propan-2-yl)oxy)-phosphoryl)-L-serine

ID: ALA4750036

PubChem CID: 78319629

Max Phase: Preclinical

Molecular Formula: C25H48NO9P

Molecular Weight: 537.63

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COC)OP(=O)(O)OC[C@H](N)C(=O)O

Standard InChI:  InChI=1S/C25H48NO9P/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)33-20-22(19-32-2)35-36(30,31)34-21-23(26)25(28)29/h10-11,22-23H,3-9,12-21,26H2,1-2H3,(H,28,29)(H,30,31)/b11-10-/t22-,23-/m0/s1

Standard InChI Key:  AWVXRDOQCOHYDO-NXDWNWMYSA-N

Molfile:  

 
     RDKit          2D

 36 35  0  0  0  0  0  0  0  0999 V2000
   17.3391  -15.5991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3381  -16.4159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0336  -15.1812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7503  -15.5713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4469  -15.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1635  -15.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8601  -15.1182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5767  -15.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2733  -15.0867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9899  -15.4767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6279  -15.1965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0105  -16.2937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3132  -16.7199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5955  -16.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8983  -16.7555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1805  -16.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4833  -16.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7655  -16.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0683  -16.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0889  -17.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0904  -13.2567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5031  -13.9665    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.9115  -13.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3817  -14.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0894  -13.9707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6740  -13.9707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9663  -14.3793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6740  -13.1535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3817  -15.1965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7971  -14.3793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2125  -14.3793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9202  -13.9707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6279  -14.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9202  -13.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6279  -12.7449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6279  -11.9277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  1 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 22 21  2  0
 23 22  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  2  0
 24 29  1  6
 25 30  1  0
 30 22  1  0
 22 31  1  0
 31 32  1  0
 32 33  1  0
 33 11  1  0
 32 34  1  1
 34 35  1  0
 35 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4750036

   (2S)-2-amino-3-[hydroxy-[(2S)-1-methoxy-3-[(Z)-octadec-9-enoyl]oxypropan-2-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: 537.63

Molecular Weight (Monoisotopic): 537.3067

AlogP: 5.13

#Rotatable Bonds: 25

Polar Surface Area: 154.61

Molecular Species: ZWITTERION

HBA: 8

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.43

CX Basic pKa: 9.38

CX LogP: 3.74

CX LogD: 0.76

Aromatic Rings: ┄

Heavy Atoms: 36

QED Weighted: 0.06

Np Likeness Score: 0.93

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