(R,Z)-3-amino-2-oleamidopropyl dihydrogen phosphate

ID: ALA3621957

PubChem CID: 10410675

Max Phase: Preclinical

Molecular Formula: C21H43N2O5P

Molecular Weight: 434.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCC/C=C\CCCCCCCC(=O)N[C@H](CN)COP(=O)(O)O

Standard InChI:  InChI=1S/C21H43N2O5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)23-20(18-22)19-28-29(25,26)27/h9-10,20H,2-8,11-19,22H2,1H3,(H,23,24)(H2,25,26,27)/b10-9-/t20-/m1/s1

Standard InChI Key:  PCWJRPGQHNDFDW-GDCKJWNLSA-N

Molfile:  

     RDKit          2D

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    9.0999    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7999    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5000    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7999   -1.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1969   -1.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1568   -2.0994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3000    0.7500    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.3000    1.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2606    0.1503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2609    1.3502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3999    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6999    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9999    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2999    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5999    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8999    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1999    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4998    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5013    2.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8013    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8027    4.5016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1027    5.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1041    6.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4041    7.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4055    9.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4450    9.6030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  1  6
  7  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
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 10 13  1  0
  1 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 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
M  END

Alternative Forms

1. Parent:

   

   ALA3621957

   [(2R)-3-amino-2-[[(Z)-octadec-9-enoyl]amino]propyl] dihydrogen phosphate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 434.56

Molecular Weight (Monoisotopic): 434.2910

AlogP: 4.58

#Rotatable Bonds: 20

Polar Surface Area: 121.88

Molecular Species: ZWITTERION

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.56

CX Basic pKa: 9.12

CX LogP: 3.64

CX LogD: 2.77

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.13

Np Likeness Score: 0.62

References

1. Gonzalez-Gil I, Zian D, Vazquez-Villa H, Ortega-Gutierrez S, Lopez-Rodriguez ML.  (2015)  The status of the lysophosphatidic acid receptor type 1 (LPA1R),  6  (1): [10.1039/C4MD00333K]

Source

Source(1):

• Scientific Literature