1-oleoyl-lysophosphatidylserine

ID: ALA1742484

PubChem CID: 9547099

Max Phase: Preclinical

Molecular Formula: C24H46NO9P

Molecular Weight: 523.60

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H46NO9P/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/h9-10,21-22,26H,2-8,11-20,25H2,1H3,(H,28,29)(H,30,31)/b10-9-/t21-,22+/m1/s1

Standard InChI Key:  JZWNYZVVZXZRRH-YFKVPUFHSA-N

Molfile:  

     RDKit          2D

 35 34  0  0  0  0  0  0  0  0999 V2000
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   -2.5699   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9565   -1.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5699   -0.2083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7968   -0.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1833   -1.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3430   -0.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1581   -1.2265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6575   -1.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6699   -0.0209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542   -1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0672   -1.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6810   -1.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2941   -1.2231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9079   -1.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5210   -1.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9086   -2.2850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1348   -1.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7478   -1.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3616   -1.5742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9747   -1.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5885   -1.5730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2016   -1.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8154   -1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5208   -1.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1333   -1.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7488   -1.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3602   -1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9756   -1.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5870   -1.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2025   -1.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8139   -1.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4293   -1.5420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 17 18  1  0
  1  5  1  0
 17 19  2  0
  8 10  1  0
 18 20  1  0
  2  3  1  1
 20 21  1  0
  8 11  2  0
 21 22  1  0
  1  6  2  0
 22 23  1  0
  9 12  1  0
 23 24  1  0
  1  2  1  0
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 12 13  1  0
 25 26  1  0
  3  7  1  0
 26 27  2  0
 13 14  1  0
 27 28  1  0
  2  4  1  0
 28 29  1  0
 14 15  1  0
 29 30  1  0
  7  8  1  0
 30 31  1  0
 13 16  1  6
 31 32  1  0
 32 33  1  0
 15 17  1  0
 33 34  1  0
  8  9  1  0
 34 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1742484

   1-(9Z-octadecenoyl)-sn-glycero-3-phosphoserine

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: 523.60

Molecular Weight (Monoisotopic): 523.2910

AlogP: 4.47

#Rotatable Bonds: 24

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: 3.14

CX LogD: 0.12

Aromatic Rings: ┄

Heavy Atoms: 35

QED Weighted: 0.06

Np Likeness Score: 1.08

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]

2. Jung S, Inoue A, Nakamura S, Kishi T, Uwamizu A, Sayama M, Ikubo M, Otani Y, Kano K, Makide K, Aoki J, Ohwada T..  (2016)  Conformational Constraint of the Glycerol Moiety of Lysophosphatidylserine Affords Compounds with Receptor Subtype Selectivity.,  59  (8): [PMID:27077565] [10.1021/acs.jmedchem.5b01925]

3. Sayama M, Inoue A, Nakamura S, Jung S, Ikubo M, Otani Y, Uwamizu A, Kishi T, Makide K, Aoki J, Hirokawa T, Ohwada T..  (2017)  Probing the Hydrophobic Binding Pocket of G-Protein-Coupled Lysophosphatidylserine Receptor GPR34/LPS1 by Docking-Aided Structure-Activity Analysis.,  60  (14): [PMID:28715213] [10.1021/acs.jmedchem.7b00693]

4. 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]

5. 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