((3-(N-hydroxyacetamido)propyl)phosphoryl)bis(oxy)bis(methylene)dibutyrate

ID: ALA2012480

PubChem CID: 70689485

Max Phase: Preclinical

Molecular Formula: C15H28NO9P

Molecular Weight: 397.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC(=O)OCOP(=O)(CCCN(O)C(C)=O)OCOC(=O)CCC

Standard InChI:  InChI=1S/C15H28NO9P/c1-4-7-14(18)22-11-24-26(21,10-6-9-16(20)13(3)17)25-12-23-15(19)8-5-2/h20H,4-12H2,1-3H3

Standard InChI Key:  UFTBRBCHGYMPTN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 25  0  0  0  0  0  0  0  0999 V2000
   12.2590   -3.2179    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.9681   -3.6396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6828   -3.5851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6725   -4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4036   -3.1872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5418   -3.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8306   -3.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4103   -2.3598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1148   -3.6054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2705   -2.3929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6878   -3.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3969   -3.6582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1166   -3.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8257   -3.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1274   -2.4301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5455   -3.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2545   -3.6953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2542   -4.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5373   -4.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5325   -5.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8156   -5.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8107   -6.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1035   -5.2666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0939   -6.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0890   -7.7415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9750   -3.1613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  9  1  0
 13 14  1  0
  6  1  1  0
 13 15  2  0
  7  6  1  0
 14 16  1  0
  8  5  1  0
 16 17  1  0
  9  7  1  0
  1 18  1  0
 18 19  1  0
  1 10  2  0
 19 20  1  0
  2  1  1  0
 20 21  1  0
  2 11  1  0
 21 22  1  0
  3  5  1  0
 21 23  2  0
 11 12  1  0
 22 24  1  0
  4  3  2  0
 24 25  1  0
 12 13  1  0
  3 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2012480

   [3-[Acetyl(hydroxy)amino]propyl-(butanoyloxymethoxy)phosphoryl]oxymethyl butanoate

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: 397.36

Molecular Weight (Monoisotopic): 397.1502

AlogP: 2.44

#Rotatable Bonds: 14

Polar Surface Area: 128.67

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.40

CX Basic pKa: ┄

CX LogP: 1.02

CX LogD: 0.98

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.15

Np Likeness Score: 0.45

References

1. Ponaire S, Zinglé C, Tritsch D, Grosdemange-Billiard C, Rohmer M..  (2012)  Growth inhibition of Mycobacterium smegmatis by prodrugs of deoxyxylulose phosphate reducto-isomerase inhibitors, promising anti-mycobacterial agents.,  51  [PMID:22405649] [10.1016/j.ejmech.2012.02.031]

Source

Source(1):

• Scientific Literature