(S)-O-(2-Hexadecanamidoisohexyl) phosphocholine

ID: ALA4524081

Max Phase: Preclinical

Molecular Formula: C27H57N2O5P

Molecular Weight: 520.74

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCC(=O)N[C@H](COP(=O)([O-])OCC[N+](C)(C)C)CC(C)C

Standard InChI:  InChI=1S/C27H57N2O5P/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-27(30)28-26(23-25(2)3)24-34-35(31,32)33-22-21-29(4,5)6/h25-26H,7-24H2,1-6H3,(H-,28,30,31,32)/t26-/m0/s1

Standard InChI Key:  VRBRGHOCXOVDKR-SANMLTNESA-N

Molfile:  

     RDKit          2D

 35 34  0  0  1  0  0  0  0  0999 V2000
    7.2229   -1.3602    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    7.2044   -0.5354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5446   -3.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2415   -2.1850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0477   -1.3387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2676   -3.8361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7049    0.0084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3937   -1.3789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5306   -2.6161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9628   -2.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9771   -3.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9645   -0.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7034   -3.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1371   -0.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0010   -0.4219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4106    0.4399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2743    0.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8394   -3.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4072   -3.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1078   -3.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4630   -3.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7397   -4.0427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2509   -3.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5457   -3.9561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8224   -3.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1172   -3.9850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6062   -3.5839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3115   -4.0097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0345   -3.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4026   -3.8984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -3.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9739   -3.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1312   -3.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3867   -2.5637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1682   -4.0716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  6  1  0
  4  1  1  0
  5  1  2  0
 11  6  1  0
  7 14  1  0
  8  1  1  0
  9  3  2  0
 10  4  1  0
 11 10  1  0
 12  8  1  0
 11 13  1  6
 14 12  1  0
 15  7  1  0
 16  7  1  0
 17  7  1  0
 18  3  1  0
 19 13  1  0
 20 18  1  0
 21 22  1  0
 22 29  1  0
 23 32  1  0
 24 23  1  0
 25 24  1  0
 26 25  1  0
 27 26  1  0
 28 27  1  0
 29 28  1  0
 30 20  1  0
 31 30  1  0
 32 31  1  0
 33 19  1  0
 34 19  1  0
 35 21  1  0
M  CHG  2   2  -1   7   1
M  END

Alternative Forms

1. Parent:

   

   ALA4524081

   ---

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: 520.74

Molecular Weight (Monoisotopic): 520.4005

AlogP: 6.21

#Rotatable Bonds: 24

Polar Surface Area: 87.69

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.87

CX Basic pKa: ┄

CX LogP: 2.76

CX LogD: 4.79

Aromatic Rings: ┄

Heavy Atoms: 35

QED Weighted: 0.09

Np Likeness Score: 0.18

References

1. Bennion C, Connolly S, Gensmantel NP, Hallam C, Jackson CG, Primrose WU, Roberts GC, Robinson DH, Slaich PK..  (1992)  Design and synthesis of some substrate analogue inhibitors of phospholipase A2 and investigations by NMR and molecular modeling into the binding interactions in the enzyme-inhibitor complex.,  35  (16): [PMID:1501221] [10.1021/jm00094a003]

Source

Source(1):

• Scientific Literature