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

ID: ALA3220030

PubChem CID: 90666782

Max Phase: Preclinical

Molecular Formula: C16H19NO4

Molecular Weight: 289.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@H](CNc2ccc3ccccc3c2)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C16H19NO4/c18-9-14-16(20)15(19)13(21-14)8-17-12-6-5-10-3-1-2-4-11(10)7-12/h1-7,13-20H,8-9H2/t13-,14-,15-,16-/m1/s1

Standard InChI Key:  HIPGJIDCVYJWPU-KLHDSHLOSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    2.6069   -3.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3837   -3.1320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9431   -2.8737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3650   -4.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2824   -3.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5428   -4.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6186   -4.9159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5067   -3.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2872   -4.9217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4819   -2.3031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9833   -3.6873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7640   -3.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3591   -4.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7163   -2.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9386   -2.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3208   -2.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1394   -3.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7363   -4.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5147   -4.0695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6929   -3.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0947   -2.7219    0.0000 C   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 17  1  0
 16 14  1  0
 14 15  2  0
 15 12  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 16  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3220030

   (2R,3S,4S,5R)-2-(hydroxymethyl)-5-[(naphthalen-2-ylamino)methyl]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: 289.33

Molecular Weight (Monoisotopic): 289.1314

AlogP: 0.73

#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: 3.87

CX LogP: 0.39

CX LogD: 0.39

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.67

Np Likeness Score: 0.44

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