(O-(hydroxy(((S)-1-(oleoyloxy)propan-2-yl)oxy)phosphoryl)-L-serine

ID: ALA4764512

PubChem CID: 78319597

Max Phase: Preclinical

Molecular Formula: C24H46NO8P

Molecular Weight: 507.61

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H46NO8P/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)31-19-21(2)33-34(29,30)32-20-22(25)24(27)28/h10-11,21-22H,3-9,12-20,25H2,1-2H3,(H,27,28)(H,29,30)/b11-10-/t21-,22-/m0/s1

Standard InChI Key:  KAAQNFPPAPNHIM-VJLWCUKXSA-N

Molfile:  

 
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    6.3349   -9.9279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4999   -7.4785    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.9083   -6.7662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3785   -7.8913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0862   -7.4827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6708   -7.4827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6708   -6.6655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3785   -8.7085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7939   -7.8913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2093   -7.8913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9170   -6.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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 22 21  2  0
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 26 28  2  0
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 32 34  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4764512

   (2S)-2-amino-3-[hydroxy-[(2S)-1-[(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: 507.61

Molecular Weight (Monoisotopic): 507.2961

AlogP: 5.50

#Rotatable Bonds: 23

Polar Surface Area: 145.38

Molecular Species: ZWITTERION

HBA: 7

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.55

CX Basic pKa: 9.38

CX LogP: 4.25

CX LogD: 1.17

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.07

Np Likeness Score: 0.82

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