Sodium salt 4-hydroxy-2-(3,4,5-trihydroxy-6-methoxy-tetrahydro-pyran-2-ylmethylsulfanyl)-butyrate

ID: ALA2112527

PubChem CID: 71461627

Max Phase: Preclinical

Molecular Formula: C11H19NaO8S

Molecular Weight: 312.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@@H]1O[C@@H](CSC(CCO)C(=O)[O-])[C@H](O)[C@H](O)[C@@H]1O.[Na+]

Standard InChI:  InChI=1S/C11H20O8S.Na/c1-18-11-9(15)8(14)7(13)5(19-11)4-20-6(2-3-12)10(16)17;/h5-9,11-15H,2-4H2,1H3,(H,16,17);/q;+1/p-1/t5-,6?,7-,8-,9-,11+;/m0./s1

Standard InChI Key:  KEJIMGYZTGIXHF-WERAIWOBSA-M

Molfile:  

     RDKit          2D

 21 20  0  0  0  0  0  0  0  0999 V2000
   10.9612   -2.5330    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    9.2833   -4.5774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7146   -5.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5340   -3.8445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2218   -5.0531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1360   -4.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0875   -4.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7368   -2.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2546   -3.1823    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.7018   -3.8445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3990   -2.4173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0682   -2.4173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7240   -1.2729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4761   -5.3103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9496   -5.2524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1360   -3.3430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0897   -4.5516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4060   -2.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7888   -0.5207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3932   -1.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0540   -5.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  5  1  0
  5  2  1  0
  6  3  1  0
  7  4  1  0
  8 12  1  0
  9 10  1  0
  7 10  1  1
 11  8  1  0
 12  9  1  0
 13  8  2  0
  2 14  1  6
  3 15  1  1
  6 16  1  1
  5 17  1  1
 18 12  1  0
 19 20  1  0
 20 18  1  0
 21 17  1  0
  6  7  1  0
M  CHG  2   1   1  11  -1
M  END

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: 312.34

Molecular Weight (Monoisotopic): 312.0879

AlogP: -1.99

#Rotatable Bonds: 7

Polar Surface Area: 136.68

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.87

CX Basic pKa: ┄

CX LogP: -2.06

CX LogD: -5.29

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.36

Np Likeness Score: 1.49

References

1. Fazli A, Bradley SJ, Kiefel MJ, Jolly C, Holmes IH, von Itzstein M..  (2001)  Synthesis and biological evaluation of sialylmimetics as rotavirus inhibitors.,  44  (20): [PMID:11563928] [10.1021/jm0100887]

Source

Source(1):

• Scientific Literature