(2R,3S,4S,5R)-2-((3,4-dichlorophenylamino)methyl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

ID: ALA3220031

PubChem CID: 90666783

Max Phase: Preclinical

Molecular Formula: C12H15Cl2NO4

Molecular Weight: 308.16

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@H](CNc2ccc(Cl)c(Cl)c2)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C12H15Cl2NO4/c13-7-2-1-6(3-8(7)14)15-4-9-11(17)12(18)10(5-16)19-9/h1-3,9-12,15-18H,4-5H2/t9-,10-,11-,12-/m1/s1

Standard InChI Key:  CNSOZTCZYCNRHJ-DDHJBXDOSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
   10.4941   -2.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2709   -2.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8303   -2.4032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2521   -3.6610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1696   -2.8910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4299   -3.6610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5058   -4.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3938   -2.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1743   -4.4512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3691   -1.8326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8704   -3.2168    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6511   -2.9752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2462   -3.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0262   -3.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2079   -2.4929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6035   -1.9367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8258   -2.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6255   -3.8461    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.9883   -2.2502    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6
  1  3  1  0
  4  1  1  0
  3  5  1  0
  4  6  1  0
  4  7  1  1
  5  8  1  1
  6  9  1  6
  8 10  1  0
  6  5  1  0
  2 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 14 18  1  0
 15 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3220031

   (2R,3S,4S,5R)-2-[(3,4-dichloroanilino)methyl]-5-(hydroxymethyl)oxolane-3,4-diol

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: 308.16

Molecular Weight (Monoisotopic): 307.0378

AlogP: 0.89

#Rotatable Bonds: 4

Polar Surface Area: 81.95

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.78

CX Basic pKa: 3.45

CX LogP: 0.60

CX LogD: 0.60

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.66

Np Likeness Score: 0.09

References

1. Lavorato SN, Andrade SF, Silva THA, Alves RJ, Oliveira RB.  (2012)  Phosphofructokinase: structural and functional aspects and design of selective inhibitors,  3  (10): [10.1039/C2MD20122D]

Source

Source(1):

• Scientific Literature