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

ID: ALA4796110

PubChem CID: 118555084

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-AYRHNUGRSA-N

Molfile:  

 
     RDKit          2D

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   22.2169  -21.0654    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   22.6253  -20.3530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0955  -21.4781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8032  -21.0695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3878  -21.0695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6801  -21.4781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3878  -20.2523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0955  -22.2953    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5109  -21.4781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9263  -21.4781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3417  -22.2953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   27.1726  -22.2953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   28.5880  -21.4799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   27.1710  -21.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8794  -23.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   29.2868  -23.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9926  -23.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6983  -23.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4041  -23.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1098  -23.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8156  -23.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5214  -23.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2271  -23.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9353  -23.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6425  -23.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6332  -21.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3417  -21.4781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0447  -21.0703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0453  -20.2538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3368  -19.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6276  -20.2560    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
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  2 11  1  0
 35 11  1  1
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 18 23  1  0
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 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:

   

   ALA4796110

   (2S)-2-amino-3-[hydroxy-[(3R,4S)-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