(O-(hydroxy(((3R,4S)-3-((3-(2-(undecyloxy)phenyl)-propanoyl)oxy)tetrahydro-2H-pyran-4-yl)oxy)phosphoryl)-L-serine)

ID: ALA4754776

PubChem CID: 118555093

Max Phase: Preclinical

Molecular Formula: C28H46NO10P

Molecular Weight: 587.65

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCOc1ccccc1CCC(=O)O[C@H]1COCC[C@H]1OP(=O)(O)OC[C@H](N)C(=O)O

Standard InChI:  InChI=1S/C28H46NO10P/c1-2-3-4-5-6-7-8-9-12-18-36-24-14-11-10-13-22(24)15-16-27(30)38-26-21-35-19-17-25(26)39-40(33,34)37-20-23(29)28(31)32/h10-11,13-14,23,25-26H,2-9,12,15-21,29H2,1H3,(H,31,32)(H,33,34)/t23-,25+,26-/m0/s1

Standard InChI Key:  FTEXYKVSENDFKC-DMDYGQEQSA-N

Molfile:  

 
     RDKit          2D

 40 41  0  0  0  0  0  0  0  0999 V2000
   21.4327  -16.3026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8454  -17.0124    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   22.2538  -16.3001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7240  -17.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4317  -17.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0163  -17.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3086  -17.4252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0163  -16.1994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7240  -18.2424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1394  -17.4252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5549  -17.4252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9703  -18.2424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6780  -18.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6780  -19.4681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3857  -18.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0934  -18.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8011  -18.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5089  -18.6529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2161  -18.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2166  -17.4269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5039  -17.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7996  -17.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5079  -19.4701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2096  -19.8767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9154  -19.4681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6211  -19.8767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3269  -19.4681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0326  -19.8767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7384  -19.4681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4441  -19.8767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1499  -19.4681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8557  -19.8767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5639  -19.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2711  -19.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2617  -17.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9703  -17.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6732  -17.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6739  -16.2008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9653  -15.7937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2562  -16.2031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  2  0
  4  9  1  6
  5 10  1  0
 10  2  1  0
  2 11  1  0
 35 11  1  6
 36 12  1  6
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 18 23  1  0
 23 24  1  0
 24 25  1  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
 33 34  1  0
 35 36  1  0
 35 40  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4754776

   (2S)-2-amino-3-[hydroxy-[(3S,4R)-3-[3-(2-undecoxyphenyl)propanoyloxy]oxan-4-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: 587.65

Molecular Weight (Monoisotopic): 587.2859

AlogP: 4.78

#Rotatable Bonds: 21

Polar Surface Area: 163.84

Molecular Species: ZWITTERION

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.51

CX Basic pKa: 9.38

CX LogP: 3.31

CX LogD: 0.26

Aromatic Rings: 1

Heavy Atoms: 40

QED Weighted: 0.10

Np Likeness Score: 0.48

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