(Z)-Octadec-9-enoic acid 2-[((S)-2-amino-2-carboxy-ethoxy)-hydroxy-phosphoryloxy]-ethyl ester

ID: ALA4779063

PubChem CID: 162663009

Max Phase: Preclinical

Molecular Formula: C23H44NO8P

Molecular Weight: 493.58

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H44NO8P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-22(25)30-18-19-31-33(28,29)32-20-21(24)23(26)27/h9-10,21H,2-8,11-20,24H2,1H3,(H,26,27)(H,28,29)/b10-9-/t21-/m0/s1

Standard InChI Key:  BXCHMYBHHDEEPP-YUQDSPFASA-N

Molfile:  

 
     RDKit          2D

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    7.8263   -7.8128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5218   -6.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.3482   -6.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0649   -6.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7615   -6.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4781   -6.8737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1161   -6.5934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8672   -5.8730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2799   -6.5829    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.6884   -5.8706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1585   -6.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8662   -6.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4508   -6.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7431   -6.9957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1585   -7.8128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5740   -6.9957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9894   -6.9957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6971   -6.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4048   -6.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4986   -7.6906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8014   -8.1168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0837   -7.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3864   -8.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6687   -7.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9715   -8.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2537   -7.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5565   -8.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5770   -9.0405    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
 13 12  2  0
 14 13  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 15 20  1  6
 16 21  1  0
 21 13  1  0
 13 22  1  0
 22 23  1  0
 23 24  1  0
 24 11  1  0
 10 25  2  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
M  END

Alternative Forms

1. Parent:

   

   ALA4779063

   ---

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: 493.58

Molecular Weight (Monoisotopic): 493.2805

AlogP: 5.11

#Rotatable Bonds: 23

Polar Surface Area: 145.38

Molecular Species: ZWITTERION

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.52

CX Basic pKa: 9.38

CX LogP: 3.78

CX LogD: 0.75

Aromatic Rings: ┄

Heavy Atoms: 33

QED Weighted: 0.08

Np Likeness Score: 0.92

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