((4-(hydroxy(methyl)amino)-4-oxobutyl)phosphoryl)bis(oxy)bis(methylene)dibutyrate

ID: ALA2012482

PubChem CID: 59053251

Max Phase: Preclinical

Molecular Formula: C15H28NO9P

Molecular Weight: 397.36

Molecule Type: Small molecule

Names and Identifiers

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

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

Standard InChI Key:  DOWGXUIUOLOBJD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 25  0  0  0  0  0  0  0  0999 V2000
   12.0632  -10.9679    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.3460  -11.3679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6347  -10.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9190  -11.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2078  -10.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4901  -11.3441    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2143  -10.1123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4835  -12.1690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7714  -11.3909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0754  -10.1430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4919  -10.9891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0583  -11.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2002  -11.4121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9207  -11.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6290  -11.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9330  -10.1854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3415  -12.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3366  -13.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6197  -13.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6149  -14.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9077  -13.0166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3495  -11.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0578  -11.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8980  -14.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8932  -15.4915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7789  -10.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  7  2  0
 13 14  1  0
  4  3  1  0
 14 15  1  0
  6  8  1  0
 14 16  2  0
 12 17  1  0
  1  9  1  0
 17 18  1  0
  4  5  1  0
 18 19  1  0
  1 10  2  0
 19 20  1  0
  2  1  1  0
 19 21  2  0
  9 11  1  0
 15 22  1  0
  5  6  1  0
 22 23  1  0
  1 12  1  0
 20 24  1  0
  3  2  1  0
 24 25  1  0
 11 13  1  0
  6 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2012482

   [Butanoyloxymethoxy-[4-[hydroxy(methyl)amino]-4-oxobutyl]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: 8.53

CX Basic pKa: ┄

CX LogP: 1.31

CX LogD: 1.28

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.15

Np Likeness Score: 0.08

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