3,4,5-trihydroxy-6-hydroxymethyl-2-phenylcarboxamidomethyltetrahydro-2H-pyran

ID: ALA180318

PubChem CID: 14542598

Max Phase: Preclinical

Molecular Formula: C14H19NO6

Molecular Weight: 297.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCC1OC(CO)C(O)C(O)C1O)c1ccccc1

Standard InChI:  InChI=1S/C14H19NO6/c16-7-10-12(18)13(19)11(17)9(21-10)6-15-14(20)8-4-2-1-3-5-8/h1-5,9-13,16-19H,6-7H2,(H,15,20)

Standard InChI Key:  LFOASNAQEMQCAC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   -1.3500    0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2083    1.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4375    1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7625    1.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2000    1.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0833    1.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3167   -0.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6792   -0.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8292    0.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0917   -0.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1750   -1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6458    0.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4375    0.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4000    2.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3000    2.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7208    2.8208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4000   -1.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8000   -2.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2542   -2.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6625   -2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8792   -3.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0
  3  1  1  0
  4  1  1  0
  5  3  1  0
  6  4  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
 10  7  2  0
 11  7  1  0
 12  1  1  0
 13  3  1  0
 14  4  1  0
 15  6  1  0
 16 15  1  0
 17 11  2  0
 18 11  1  0
 19 17  1  0
 20 18  2  0
 21 20  1  0
  2  5  1  0
 21 19  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA180318

   N-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]methyl]benzamide

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: 297.31

Molecular Weight (Monoisotopic): 297.1212

AlogP: -1.74

#Rotatable Bonds: 4

Polar Surface Area: 119.25

Molecular Species: NEUTRAL

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.59

CX Basic pKa: ┄

CX LogP: -1.63

CX LogD: -1.63

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.45

Np Likeness Score: 0.48

References

1. Hakamata W, Muroi M, Kadokura K, Nishio T, Oku T, Kimura A, Chiba S, Takatsuki A..  (2005)  Aglycon specificity profiling of alpha-glucosidases using synthetic probes.,  15  (5): [PMID:15713413] [10.1016/j.bmcl.2004.12.086]

Source

Source(1):

• Scientific Literature