(5S,6S,7S,7aR)-5-(hydroxymethyl)-3-(octylimino)hexahydropyrrolo[1,2-c]thiazole-6,7-diol

ID: ALA3916051

PubChem CID: 134143157

Max Phase: Preclinical

Molecular Formula: C15H28N2O3S

Molecular Weight: 316.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCC/N=C1/SC[C@H]2[C@H](O)[C@@H](O)[C@H](CO)N12

Standard InChI:  InChI=1S/C15H28N2O3S/c1-2-3-4-5-6-7-8-16-15-17-11(9-18)13(19)14(20)12(17)10-21-15/h11-14,18-20H,2-10H2,1H3/b16-15+/t11-,12-,13-,14-/m0/s1

Standard InChI Key:  GRVKSWAJFYZCRD-PTRXRCKUSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    2.0172   -8.0220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0973   -7.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2810   -7.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8086   -6.5830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5848   -6.6012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2366   -8.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6369   -7.7087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3406   -8.0399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6717   -8.5056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9078   -9.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7228   -9.3021    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9901   -8.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4142   -9.9370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6034   -9.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1969  -10.5368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6055  -11.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2010  -11.9483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6096  -12.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2052  -13.3598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6137  -14.0656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2093  -14.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167   -7.4579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0
  8  2  1  0
  2  3  1  0
  3  1  1  0
  3  4  1  6
  2  5  1  1
  1  6  1  1
  6  7  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
 10 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  8 22  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3916051

   ---

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: 316.47

Molecular Weight (Monoisotopic): 316.1821

AlogP: 1.22

#Rotatable Bonds: 8

Polar Surface Area: 76.29

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.18

CX Basic pKa: 6.32

CX LogP: 1.84

CX LogD: 1.81

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.59

Np Likeness Score: 0.63

References

1. Miyawaki S, Hirokami Y, Kinami K, Hoshino M, Minehira D, Miyamoto D, Nash RJ, Fleet GW, Adachi I, Toyooka N, Kato A..  (2017)  Strategy for designing selective α-l-rhamnosidase inhibitors: Synthesis and biological evaluation of l-DMDP cyclic isothioureas.,  25  (1): [PMID:27789075] [10.1016/j.bmc.2016.10.015]

Source

Source(1):

• Scientific Literature