(2R,3S,4S,5S)-2-(hydroxymethyl)-6-(undecylamino)-2,3,4,5-tetrahydropyridine-3,4,5-triol

ID: ALA4091969

PubChem CID: 137653681

Max Phase: Preclinical

Molecular Formula: C17H34N2O4

Molecular Weight: 330.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCNC1=N[C@H](CO)[C@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C17H34N2O4/c1-2-3-4-5-6-7-8-9-10-11-18-17-16(23)15(22)14(21)13(12-20)19-17/h13-16,20-23H,2-12H2,1H3,(H,18,19)/t13-,14+,15+,16-/m1/s1

Standard InChI Key:  OPJTVWWSISLBHY-FXUDXRNXSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
    7.5070   -7.5183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9499  -12.0652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3840  -13.7201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9499  -13.7202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2372  -13.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7981   -8.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2159   -6.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2196   -7.1025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6710  -12.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8018   -9.5839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8913  -12.5992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0929  -10.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2372  -12.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0891   -9.9995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3802  -11.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9248   -5.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5107   -8.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5201  -12.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9500  -14.5477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6710  -13.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3840  -12.0652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5201  -13.7202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9285   -5.8619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 17  1  1  0
  9 21  1  0
  5 13  1  0
 11 18  1  0
 14 10  1  0
 20  3  1  6
 23 16  1  0
 13  2  1  0
  2  9  2  0
 12 14  1  0
  4  5  1  0
  5 22  1  1
  4 19  1  1
  9 20  1  0
  6 17  1  0
 20  4  1  0
 21 15  1  0
  1  8  1  0
 10  6  1  0
  8  7  1  0
  7 23  1  0
 15 12  1  0
 13 18  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4091969

   ---

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: 330.47

Molecular Weight (Monoisotopic): 330.2519

AlogP: 0.96

#Rotatable Bonds: 11

Polar Surface Area: 105.31

Molecular Species: NEUTRAL

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.47

CX Basic pKa: 7.96

CX LogP: 1.31

CX LogD: 0.65

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.36

Np Likeness Score: 0.72

References

1. Pickens JB, Wang F, Striegler S..  (2017)  Picomolar inhibition of β-galactosidase (bovine liver) attributed to loop closure.,  25  (20): [PMID:28844803] [10.1016/j.bmc.2017.07.020]

Source

Source(1):

• Scientific Literature