ethyl hydrogen4-(phthalimido)butylphosphonate

ID: ALA390336

PubChem CID: 44423075

Max Phase: Preclinical

Molecular Formula: C14H18NO5P

Molecular Weight: 311.27

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  CCOP(=O)(O)CCCCN1C(=O)c2ccccc2C1=O

Standard InChI:  InChI=1S/C14H18NO5P/c1-2-20-21(18,19)10-6-5-9-15-13(16)11-7-3-4-8-12(11)14(15)17/h3-4,7-8H,2,5-6,9-10H2,1H3,(H,18,19)

Standard InChI Key:  BKSQTRSOZDSHIO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   -4.5928   -6.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5940   -7.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8791   -7.6438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8809   -5.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1657   -6.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1608   -7.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3689   -7.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8844   -6.8080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3768   -6.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1265   -5.3526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1094   -8.2663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0594   -6.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6428   -7.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1822   -7.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5989   -8.2222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4238   -8.2173    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.2456   -8.2161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4207   -7.3924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4299   -9.0422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6592   -8.9298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4841   -8.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  2  0
  5  6  1  0
  7 11  2  0
  8 12  1  0
  2  3  1  0
 12 13  1  0
  3  6  2  0
 13 14  1  0
  1  2  2  0
 14 15  1  0
  5  4  2  0
 15 16  1  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 16 18  2  0
  8  9  1  0
 16 19  1  0
  9  5  1  0
 17 20  1  0
  4  1  1  0
 20 21  1  0
M  END

Alternative Forms

Associated Targets(non-human)

fbpC Fibonectin-binding protein C (60 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 311.27Molecular Weight (Monoisotopic): 311.0923AlogP: 2.28#Rotatable Bonds: 7
Polar Surface Area: 83.91Molecular Species: ACIDHBA: 4HBD: 1
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: 1.93CX Basic pKa: CX LogP: 0.84CX LogD: -1.46
Aromatic Rings: 1Heavy Atoms: 21QED Weighted: 0.47Np Likeness Score: -0.37

References

1. Gobec S, Plantan I, Mravljak J, Svajger U, Wilson RA, Besra GS, Soares SL, Appelberg R, Kikelj D..  (2007)  Design, synthesis, biochemical evaluation and antimycobacterial action of phosphonate inhibitors of antigen 85C, a crucial enzyme involved in biosynthesis of the mycobacterial cell wall.,  42  (1): [PMID:17010479] [10.1016/j.ejmech.2006.08.007]

Source