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

ID: ALA1278173

PubChem CID: 49836536

Max Phase: Preclinical

Molecular Formula: C18H36NO8P

Molecular Weight: 425.46

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H36NO8P/c1-2-3-4-5-6-7-8-9-10-13-18(21)26-15-12-11-14-19(22)17(20)16-27-28(23,24)25/h22H,2-16H2,1H3,(H2,23,24,25)

Standard InChI Key:  SEIMCLOQPHTQIO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 27  0  0  0  0  0  0  0  0999 V2000
   10.1833   -3.6333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8958   -3.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6083   -3.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3208   -3.2167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0333   -3.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7458   -3.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4583   -3.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1708   -3.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8833   -3.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4684   -3.2217    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.7544   -3.6350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0500   -2.6333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8792   -2.6333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6101   -4.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3190   -2.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5965   -3.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3123   -3.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5938   -2.3769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0254   -3.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7412   -3.6075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4544   -3.1928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1701   -3.6030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8833   -3.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5991   -3.5984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3122   -3.1836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0280   -3.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7412   -3.1791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4569   -3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  5  6  1  0
 22 23  1  0
 10 12  2  0
 23 24  1  0
  1  2  1  0
 24 25  1  0
 10 13  1  0
 25 26  1  0
  6  7  1  0
 26 27  1  0
  3 14  2  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1278173

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

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: 425.46

Molecular Weight (Monoisotopic): 425.2179

AlogP: 3.56

#Rotatable Bonds: 18

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: 3.28

CX LogD: -0.24

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.10

Np Likeness Score: 0.49

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