4-(N-hydroxy-2-(phosphonooxy)acetamido)butyl hexanoate

ID: ALA1278086

PubChem CID: 49836534

Max Phase: Preclinical

Molecular Formula: C12H24NO8P

Molecular Weight: 341.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCC(=O)OCCCCN(O)C(=O)COP(=O)(O)O

Standard InChI:  InChI=1S/C12H24NO8P/c1-2-3-4-7-12(15)20-9-6-5-8-13(16)11(14)10-21-22(17,18)19/h16H,2-10H2,1H3,(H2,17,18,19)

Standard InChI Key:  QCADYHRFELDWBS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 21  0  0  0  0  0  0  0  0999 V2000
   -4.1168   -3.8126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4043   -3.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6918   -3.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9793   -3.3959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2667   -3.8043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5543   -3.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1583   -3.8001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8708   -3.3876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5834   -3.7959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8318   -3.4010    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5457   -3.8143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2501   -2.8126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4209   -2.8126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6900   -4.6334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9811   -2.5708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2965   -3.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0124   -3.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2938   -2.5561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7256   -3.3766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4413   -3.7868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1546   -3.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8703   -3.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
 10 12  2  0
  1  2  1  0
 10 13  1  0
  6  7  1  0
  3 14  2  0
  3  4  1  0
  4 15  1  0
  7  8  1  0
  9 16  1  0
 16 17  1  0
  8  9  1  0
 16 18  2  0
  4  5  1  0
 17 19  1  0
  1 10  1  0
 19 20  1  0
  2  3  1  0
 20 21  1  0
 10 11  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1278086

   4-(N-hydroxy-2-(phosphonooxy)acetamido)butyl hexanoate

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: 341.30

Molecular Weight (Monoisotopic): 341.1240

AlogP: 1.22

#Rotatable Bonds: 12

Polar Surface Area: 133.60

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.31

CX Basic pKa: ┄

CX LogP: 0.61

CX LogD: -2.90

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.16

Np Likeness Score: 0.57

References

1. Daher R, Coinçon M, Fonvielle M, Gest PM, Guerin ME, Jackson M, Sygusch J, Therisod M..  (2010)  Rational design, synthesis, and evaluation of new selective inhibitors of microbial class II (zinc dependent) fructose bis-phosphate aldolases.,  53  (21): [PMID:20929256] [10.1021/jm1009814]

Source

Source(1):

• Scientific Literature