O-(hydroxy((R)-2-hydroxy-3-(3-(3-(undecyloxy)phenyl)propanamido)propoxy)phosphoryl)-N-pivaloyl-L-serine

ID: ALA5180950

PubChem CID: 168275621

Max Phase: Preclinical

Molecular Formula: C31H53N2O10P

Molecular Weight: 644.74

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCOc1cccc(CCC(=O)NC[C@@H](O)COP(=O)(O)OC[C@H](NC(=O)C(C)(C)C)C(=O)O)c1

Standard InChI:  InChI=1S/C31H53N2O10P/c1-5-6-7-8-9-10-11-12-13-19-41-26-16-14-15-24(20-26)17-18-28(35)32-21-25(34)22-42-44(39,40)43-23-27(29(36)37)33-30(38)31(2,3)4/h14-16,20,25,27,34H,5-13,17-19,21-23H2,1-4H3,(H,32,35)(H,33,38)(H,36,37)(H,39,40)/t25-,27+/m1/s1

Standard InChI Key:  QPUOMUAWXDFZQT-VPUSJEBWSA-N

Molfile:  

 
     RDKit          2D

 44 44  0  0  0  0  0  0  0  0999 V2000
   -7.1472    0.0001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8617   -0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8617   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1472   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5763   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8617   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5763    0.0001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5763    0.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2910    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2910    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0054    0.8248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8619    1.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1472    0.8256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4325    1.2379    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0192    1.9538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7177    0.8256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0031    1.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2883    0.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2883   -0.0264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5736    1.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8589    0.8256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1443    1.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4295    0.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7148    1.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0002    0.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0002   -0.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7143   -0.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290   -0.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    0.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1437    1.2379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8584    0.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5731    1.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2878    0.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0025    1.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7172    0.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4320    1.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1466    0.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8613    1.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5761    0.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2908    1.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0054    0.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7143    1.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1443    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8443    1.9538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  7  2  1  0
  8  7  1  6
  8  9  1  0
  9 10  2  0
  9 11  1  0
 12  8  1  0
 13 12  1  0
 14 13  1  0
 14 15  2  0
 16 14  1  0
 17 16  1  0
 18 17  1  0
 18 19  1  1
 20 18  1  0
 21 20  1  0
 22 21  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  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
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 29 42  2  0
 25 42  1  0
 43 22  2  0
 14 44  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5180950

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 644.74

Molecular Weight (Monoisotopic): 644.3438

AlogP: 4.76

#Rotatable Bonds: 24

Polar Surface Area: 180.72

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.89

CX Basic pKa: ┄

CX LogP: 5.20

CX LogD: -0.44

Aromatic Rings: 1

Heavy Atoms: 44

QED Weighted: 0.08

Np Likeness Score: -0.10

References

1. Sayama M, Uwamizu A, Ikubo M, Chen L, Yan G, Otani Y, Inoue A, Aoki J, Ohwada T..  (2021)  Switching Lysophosphatidylserine G Protein-Coupled Receptor Agonists to Antagonists by Acylation of the Hydrophilic Serine Amine.,  64  (14.0): [PMID:34233115] [10.1021/acs.jmedchem.1c00347]

Source

Source(1):

• Scientific Literature