(5aS,6S,7S,8R)-6,7,8-trihydroxy-6,7,8,9-tetrahydro-5aH,11H-pyrido[2,1-b][1,3]benzothiazin-11-one

ID: ALA2018791

PubChem CID: 57404478

Max Phase: Preclinical

Molecular Formula: C12H13NO4S

Molecular Weight: 267.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1c2ccccc2S[C@H]2[C@@H](O)[C@@H](O)[C@H](O)CN12

Standard InChI:  InChI=1S/C12H13NO4S/c14-7-5-13-11(17)6-3-1-2-4-8(6)18-12(13)10(16)9(7)15/h1-4,7,9-10,12,14-16H,5H2/t7-,9+,10+,12+/m1/s1

Standard InChI Key:  QSTIQBJVDMSSEK-NKIYYHGXSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
    6.5286   -6.1469    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8128   -5.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8128   -4.9094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5286   -4.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2445   -4.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2445   -5.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9562   -4.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6721   -4.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6721   -5.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9562   -6.1469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0969   -6.1469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3852   -5.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3852   -4.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0969   -4.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5286   -3.6719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6693   -4.4969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6693   -6.1469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0969   -6.9719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8128   -6.5594    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  2  0
  9 10  1  0
  6 10  2  0
  5  7  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  2 11  1  0
  3 14  1  0
  4 15  2  0
 13 16  1  6
 12 17  1  1
 11 18  1  1
  2 19  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2018791

   (5aS,6S,7S,8R)-6,7,8-trihydroxy-6,7,8,9-tetrahydro-5aH-pyrido[2,1-b][1,3]benzothiazin-11-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: 267.31

Molecular Weight (Monoisotopic): 267.0565

AlogP: -0.34

#Rotatable Bonds: ┄

Polar Surface Area: 81.00

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.78

CX Basic pKa: ┄

CX LogP: -0.40

CX LogD: -0.40

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.60

Np Likeness Score: 0.22

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]

2. Chen H, Hao L, Zhu M, Yang T, Wei S, Qin Z, Zhang P, Li X..  (2014)  Synthesis of bi-/tricyclic azasugars fused thiazinan-4-one and their HIV-RT inhibitory activity.,  24  (15): [PMID:24953602] [10.1016/j.bmcl.2014.05.079]

Source

Source(1):

• Scientific Literature