(2S,4S)-4-[(S)-(3,4-dihydroxypyrrolidin-2-yl)(hydroxy)methyl]-6-(hydroxymethyl)oxane-2,3,5-triol

ID: ALA354875

PubChem CID: 44382387

Max Phase: Preclinical

Molecular Formula: C11H21NO8

Molecular Weight: 295.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OCC1O[C@H](O)C(O)[C@@H]([C@H](O)C2NCC(O)C2O)C1O

Standard InChI:  InChI=1S/C11H21NO8/c13-2-4-8(16)5(10(18)11(19)20-4)9(17)6-7(15)3(14)1-12-6/h3-19H,1-2H2/t3?,4?,5-,6?,7?,8?,9+,10?,11+/m1/s1

Standard InChI Key:  UBZKRZZOBAAKDP-XBLUSGFPSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  1  0  0  0  0  0999 V2000
    6.1000   -6.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6750   -6.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3875   -6.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0042   -5.5792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5125   -5.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4750   -6.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0542   -6.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4167   -6.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1375   -5.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5917   -5.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5917   -6.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -6.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3875   -7.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9042   -7.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2667   -7.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0500   -7.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8750   -4.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1125   -7.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917   -4.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1542   -4.4667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2584   -7.0541    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  1  3  1  0
  4  2  1  0
  5 10  1  0
  6  7  1  0
  7  1  1  0
  8  2  1  0
  9  1  1  0
 10  9  1  0
 11  8  1  0
 12  4  1  0
  3 13  1  6
 14  8  1  0
  6 15  1  6
 16  7  1  0
 17  9  1  0
 18 11  1  0
 19 10  1  0
 20 19  1  0
  6  5  1  0
 12 11  1  0
  1 21  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA354875

   (2S,4S)-4-[(S)-(3,4-dihydroxypyrrolidin-2-yl)-hydroxymethyl]-6-(hydroxymethyl)oxane-2,3,5-triol

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: 295.29

Molecular Weight (Monoisotopic): 295.1267

AlogP: -4.91

#Rotatable Bonds: 3

Polar Surface Area: 162.87

Molecular Species: BASE

HBA: 9

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.40

CX Basic pKa: 8.97

CX LogP: -4.62

CX LogD: -6.19

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.25

Np Likeness Score: 2.16

References

1. Kraehenbuehl K, Picasso S, Vogel P.  (1997)  Dihydroxypyrrolidines C-linked to galactose. Total synthesis of a specific inhibitor of -mannosidases,  7  (7): [10.1016/S0960-894X(97)00135-2]

Source

Source(1):

• Scientific Literature