(O-((((R)-1-(Benzyloxy)-3-(oleoyloxy)-propan-2-yl)oxy)(hydroxy)phosphoryl)-L-serine)

ID: ALA4746971

PubChem CID: 118584208

Max Phase: Preclinical

Molecular Formula: C31H52NO9P

Molecular Weight: 613.73

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@@H](COCc1ccccc1)OP(=O)(O)OC[C@H](N)C(=O)O

Standard InChI:  InChI=1S/C31H52NO9P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-22-30(33)39-25-28(24-38-23-27-20-17-16-18-21-27)41-42(36,37)40-26-29(32)31(34)35/h9-10,16-18,20-21,28-29H,2-8,11-15,19,22-26,32H2,1H3,(H,34,35)(H,36,37)/b10-9-/t28-,29+/m1/s1

Standard InChI Key:  CLPCIRZHATVKCL-BDZCPYMJSA-N

Molfile:  

 
     RDKit          2D

 42 42  0  0  0  0  0  0  0  0999 V2000
   30.6989  -27.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6980  -27.9226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3935  -26.6879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1101  -27.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8067  -26.6564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5233  -27.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2199  -26.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9365  -27.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6331  -26.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3498  -26.9834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9878  -26.7032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.3703  -27.8004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6731  -28.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9553  -27.8359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2581  -28.2622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5404  -27.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8431  -28.2977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1254  -27.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4282  -28.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4487  -29.1502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4502  -24.7634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8629  -25.4733    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   28.2713  -24.7609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7415  -25.8860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4492  -25.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0338  -25.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3261  -25.8860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0338  -24.6602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7415  -26.7032    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.1569  -25.8860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5724  -25.8860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2801  -25.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9878  -25.8860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2801  -24.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9878  -24.2516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.6955  -24.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4032  -24.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1109  -24.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8181  -24.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8186  -23.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1059  -23.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4016  -23.4382    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  6
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  2  0
 42 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4746971

   (2S)-2-amino-3-[hydroxy-[(2R)-1-[(Z)-octadec-9-enoyl]oxy-3-phenylmethoxypropan-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: 613.73

Molecular Weight (Monoisotopic): 613.3380

AlogP: 6.70

#Rotatable Bonds: 27

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: 5.46

CX LogD: 2.49

Aromatic Rings: 1

Heavy Atoms: 42

QED Weighted: 0.04

Np Likeness Score: 0.62

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