(8R,9R,10R,10aR)-8,9,10-trihydroxy-8,9,10,10a-tetrahydro-5H,7H-dipyrido[2,1-b:3',2'-e][1,3]thiazin-5-one

ID: ALA2018796

PubChem CID: 70689671

Max Phase: Preclinical

Molecular Formula: C11H12N2O4S

Molecular Weight: 268.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1c2cccnc2S[C@@H]2[C@H](O)[C@H](O)[C@H](O)CN12

Standard InChI:  InChI=1S/C11H12N2O4S/c14-6-4-13-10(17)5-2-1-3-12-9(5)18-11(13)8(16)7(6)15/h1-3,6-8,11,14-16H,4H2/t6-,7-,8-,11-/m1/s1

Standard InChI Key:  LJGUVDUHFUMXES-KCGFPETGSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
    6.4328   -5.8052    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.7169   -5.3927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7169   -4.5677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4328   -4.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1487   -4.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1487   -5.3927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0011   -5.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2894   -5.3927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2894   -4.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0011   -4.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8604   -4.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5762   -4.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5762   -5.3927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8604   -5.8052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4328   -3.3302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0011   -6.6302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5735   -5.8052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5735   -4.1552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7169   -6.2177    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  2  7  1  0
  3 10  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  5 11  2  0
  6 14  2  0
  4 15  2  0
  7 16  1  6
  8 17  1  6
  9 18  1  6
  2 19  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA2018796

   (10R,11R,12R,13R)-11,12,13-trihydroxy-9-thia-1,7-diazatricyclo[8.4.0.03,8]tetradeca-3(8),4,6-trien-2-one

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: 268.29

Molecular Weight (Monoisotopic): 268.0518

AlogP: -0.95

#Rotatable Bonds: ┄

Polar Surface Area: 93.89

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.77

CX Basic pKa: 1.99

CX LogP: -1.02

CX LogD: -1.02

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.56

Np Likeness Score: 0.15

References

1. Li X, Qin Z, Yang T, Zhang H, Wei S, Li C, Chen H, Meng M..  (2012)  Synthesis and biological activity of bi/tricyclic azasugars fused thiazolidin-4-one and thiazinan-4-one by microwave-assisted tandem Staudinger/aza-Wittig/cyclization.,  22  (8): [PMID:22437112] [10.1016/j.bmcl.2012.02.103]

Source

Source(1):

• Scientific Literature