(2R,3S,4R,5R,6S)-2-(hydroxymethyl)-6-(5-phenyl-1H-pyrrol-2-yl)tetrahydro-2H-pyran-3,4,5-triol

ID: ALA3968658

PubChem CID: 134151228

Max Phase: Preclinical

Molecular Formula: C16H19NO5

Molecular Weight: 305.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@@H](c2ccc(-c3ccccc3)[nH]2)[C@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C16H19NO5/c18-8-12-13(19)14(20)15(21)16(22-12)11-7-6-10(17-11)9-4-2-1-3-5-9/h1-7,12-21H,8H2/t12-,13-,14+,15-,16+/m1/s1

Standard InChI Key:  ROSASTJVOMNUMC-LJIZCISZSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    1.6042  -12.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6042  -12.9210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3163  -13.3294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0282  -12.9210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0282  -12.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3163  -11.6793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7439  -11.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7422  -13.3346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3163  -14.1544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8903  -13.3346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8885  -11.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8861  -10.8606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4934  -12.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0472  -11.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6369  -10.6972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8294  -10.8665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9746   -9.9445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7939   -9.8630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1316   -9.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6484   -8.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8237   -8.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4898   -9.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  1
  4  8  1  6
  3  9  1  1
  2 10  1  6
  1 11  1  1
 11 12  1  0
  7 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16  7  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3968658

   ---

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: 305.33

Molecular Weight (Monoisotopic): 305.1263

AlogP: 0.20

#Rotatable Bonds: 3

Polar Surface Area: 105.94

Molecular Species: NEUTRAL

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.58

CX Basic pKa: ┄

CX LogP: -0.22

CX LogD: -0.22

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.56

Np Likeness Score: 0.84

References

1. Kantsadi AL, Bokor É, Kun S, Stravodimos GA, Chatzileontiadou DSM, Leonidas DD, Juhász-Tóth É, Szakács A, Batta G, Docsa T, Gergely P, Somsák L..  (2016)  Synthetic, enzyme kinetic, and protein crystallographic studies of C-β-d-glucopyranosyl pyrroles and imidazoles reveal and explain low nanomolar inhibition of human liver glycogen phosphorylase.,  123  [PMID:27522507] [10.1016/j.ejmech.2016.06.049]

Source

Source(1):

• Scientific Literature