N-((2R,3R,4R,5S,6R)-2-(cyclohexylthio)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide

ID: ALA1090110

PubChem CID: 46885316

Max Phase: Preclinical

Molecular Formula: C14H25NO5S

Molecular Weight: 319.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1SC1CCCCC1

Standard InChI:  InChI=1S/C14H25NO5S/c1-8(17)15-11-13(19)12(18)10(7-16)20-14(11)21-9-5-3-2-4-6-9/h9-14,16,18-19H,2-7H2,1H3,(H,15,17)/t10-,11-,12-,13-,14-/m1/s1

Standard InChI Key:  MIYMEIQEBJEQPX-DHGKCCLASA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    5.0500   -6.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0500   -7.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7620   -7.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4740   -7.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4740   -6.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7620   -5.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1879   -7.4802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1867   -8.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4716   -8.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9006   -8.7187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7620   -8.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3361   -7.4802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3343   -5.8313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6211   -6.2459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1897   -5.8313    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.1921   -5.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9079   -4.5987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9123   -3.7773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2008   -3.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4834   -3.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4773   -4.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  3 11  1  1
  4  5  1  0
  2 12  1  6
  5  6  1  0
  1 13  1  1
 13 14  1  0
  4  7  1  6
  5 15  1  6
  1  2  1  0
 15 16  1  0
 16 17  1  0
  7  8  1  0
  1  6  1  0
  8  9  1  0
  2  3  1  0
  8 10  2  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1090110

   N-[(2R,3R,4R,5S,6R)-2-cyclohexylsulfanyl-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

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: 319.42

Molecular Weight (Monoisotopic): 319.1453

AlogP: 0.00

#Rotatable Bonds: 4

Polar Surface Area: 99.02

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.67

CX Basic pKa: ┄

CX LogP: -0.27

CX LogD: -0.27

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.58

Np Likeness Score: 0.87

References

1. Gammon DW, Steenkamp DJ, Mavumengwana V, Marakalala MJ, Mudzunga TT, Hunter R, Munyololo M..  (2010)  Conjugates of plumbagin and phenyl-2-amino-1-thioglucoside inhibit MshB, a deacetylase involved in the biosynthesis of mycothiol.,  18  (7): [PMID:20304659] [10.1016/j.bmc.2010.02.049]

Source

Source(1):

• Scientific Literature