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

ID: ALA4755564

PubChem CID: 118555095

Max Phase: Preclinical

Molecular Formula: C28H46NO10P

Molecular Weight: 587.65

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCOc1ccccc1CCC(=O)O[C@H]1CCOC[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)38-25-17-19-35-21-26(25)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:  WTHILFAMRXZBRN-RNXOBYDBSA-N

Molfile:  

 
     RDKit          2D

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    4.8452  -27.2785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3154  -28.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0231  -27.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6077  -27.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6077  -27.1778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3154  -29.2208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   12.9182  -30.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6240  -30.8552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3297  -30.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5567  -26.7721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8475  -27.1815    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
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 31 32  1  0
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 35 36  1  0
 35 40  1  0
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 37 38  1  0
 38 39  1  0
 39 40  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4755564

   (2S)-2-amino-3-[hydroxy-[(3S,4S)-4-[3-(2-undecoxyphenyl)propanoyloxy]oxan-3-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: 1.44

CX Basic pKa: 9.38

CX LogP: 3.25

CX LogD: 0.26

Aromatic Rings: 1

Heavy Atoms: 40

QED Weighted: 0.10

Np Likeness Score: 0.46

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