4-Methyl-6-phenethylamino-cyclohexane-1,2,3-triol

ID: ALA2114289

PubChem CID: 71461694

Max Phase: Preclinical

Molecular Formula: C15H23NO3

Molecular Weight: 265.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1CC(NCCc2ccccc2)[C@@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C15H23NO3/c1-10-9-12(14(18)15(19)13(10)17)16-8-7-11-5-3-2-4-6-11/h2-6,10,12-19H,7-9H2,1H3/t10-,12?,13-,14-,15+/m1/s1

Standard InChI Key:  AYJDCDFTVZFKTB-UJNYZWNZSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
    0.9537   -3.3109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8783   -3.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3290   -3.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2906   -2.9153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7288   -2.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6159   -3.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2781   -2.0907    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9537   -4.1272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7029   -3.6357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3290   -4.3604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9902   -1.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4145   -1.6659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958   -2.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7024   -2.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1392   -2.0740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4145   -0.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1267   -0.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8513   -1.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8388   -0.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6  5  1  0
  4  7  1  0
  1  8  1  6
  2  9  1  1
  3 10  1  6
 11  7  1  0
 12 14  1  0
  5 13  1  6
 14 11  1  0
 15 12  1  0
 16 12  2  0
 17 16  1  0
 18 15  2  0
 19 17  2  0
  6  4  1  0
 19 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2114289

   (1R,2S,3R,4R)-4-methyl-6-(2-phenylethylamino)cyclohexane-1,2,3-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: 265.35

Molecular Weight (Monoisotopic): 265.1678

AlogP: 0.31

#Rotatable Bonds: 4

Polar Surface Area: 72.72

Molecular Species: BASE

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.97

CX Basic pKa: 9.22

CX LogP: 0.76

CX LogD: -1.05

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.63

Np Likeness Score: 0.94

References

1. Ogawa S, Fujieda S, Sakata Y, Ishizaki M, Hisamatsu S, Okazaki K..  (2003)  Synthesis and glycosidase inhibitory activity of some N-substituted 6-deoxy-5a-carba-beta-DL- and L-galactopyranosylamines.,  13  (20): [PMID:14505649] [10.1016/s0960-894x(03)00742-x]

2. Ogawa S, Fujieda S, Sakata Y, Ishizaki M, Hisamatsu S, Okazaki K..  (2003)  Synthesis and glycosidase inhibitory activity of some N-substituted 6-deoxy-5a-carba-beta-DL- and L-galactopyranosylamines.,  13  (20): [PMID:14505649] [10.1016/s0960-894x(03)00742-x]

Source

Source(1):

• Scientific Literature