2-((((S)-3-acetamido-3-carboxylatopropyl)oxidophosphoryl)methyl)pentanedioate

ID: ALA2401838

PubChem CID: 71728232

Max Phase: Preclinical

Molecular Formula: C12H20NO9P

Molecular Weight: 353.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@@H](CCP(=O)(O)CC(CCC(=O)O)C(=O)O)C(=O)O

Standard InChI:  InChI=1S/C12H20NO9P/c1-7(14)13-9(12(19)20)4-5-23(21,22)6-8(11(17)18)2-3-10(15)16/h8-9H,2-6H2,1H3,(H,13,14)(H,15,16)(H,17,18)(H,19,20)(H,21,22)/t8?,9-/m0/s1

Standard InChI Key:  PTZXXIYPZPFQTH-GKAPJAKFSA-N

Molfile:  

     RDKit          2D

 23 22  0  0  0  0  0  0  0  0999 V2000
   21.6721   -5.1797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2540   -4.6019    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   21.4626   -4.3868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9639   -2.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6716   -2.1544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2562   -2.1544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2562   -1.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5485   -0.9286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9639   -0.9286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9639   -3.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3793   -2.5630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6716   -1.3372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2562   -3.7888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9639   -5.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9639   -5.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6716   -6.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3793   -5.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0870   -6.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7947   -5.8318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0870   -7.0576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2562   -6.2404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5485   -5.8318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2562   -7.0576    0.0000 O   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  6
  6  7  1  0
  7  8  1  0
  7  9  2  0
  4 10  1  0
  5 11  2  0
  5 12  1  0
 10 13  1  0
 13  2  1  0
  2 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 15 21  1  0
 21 22  1  0
 21 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2401838

   2-[[[(3S)-3-acetamido-3-carboxypropyl]-hydroxyphosphoryl]methyl]pentanedioic acid

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: 353.26

Molecular Weight (Monoisotopic): 353.0876

AlogP: -0.20

#Rotatable Bonds: 11

Polar Surface Area: 178.30

Molecular Species: ACID

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.92

CX Basic pKa: ┄

CX LogP: -2.32

CX LogD: -13.88

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.31

Np Likeness Score: 0.50

References

1. Liu Y, Garnham CP, Roll-Mecak A, Tanner ME..  (2013)  Phosphinic acid-based inhibitors of tubulin polyglutamylases.,  23  (15): [PMID:23777780] [10.1016/j.bmcl.2013.05.069]

Source

Source(1):

• Scientific Literature