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

ID: ALA238766

PubChem CID: 44435080

Max Phase: Preclinical

Molecular Formula: C23H28ClNO6S

Molecular Weight: 482.00

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1SC1CCCCC1)c1ccc(-c2ccc(Cl)cc2)o1

Standard InChI:  InChI=1S/C23H28ClNO6S/c24-14-8-6-13(7-9-14)16-10-11-17(30-16)22(29)25-19-21(28)20(27)18(12-26)31-23(19)32-15-4-2-1-3-5-15/h6-11,15,18-21,23,26-28H,1-5,12H2,(H,25,29)/t18-,19-,20-,21-,23-/m0/s1

Standard InChI Key:  KMHARQIVVWZGJD-JSSYZSAGSA-N

Molfile:  

     RDKit          2D

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   -2.2127  -19.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1885  -18.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1892  -17.4066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9055  -16.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6099  -18.2455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8930  -18.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3358  -17.0097    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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  7  8  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA238766

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

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: 482.00

Molecular Weight (Monoisotopic): 481.1326

AlogP: 3.20

#Rotatable Bonds: 6

Polar Surface Area: 112.16

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.90

CX Basic pKa: ┄

CX LogP: 2.81

CX LogD: 2.81

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.50

Np Likeness Score: -0.11

References

1. Metaferia BB, Fetterolf BJ, Shazad-Ul-Hussan S, Moravec M, Smith JA, Ray S, Gutierrez-Lugo MT, Bewley CA..  (2007)  Synthesis of natural product-inspired inhibitors of Mycobacterium tuberculosis mycothiol-associated enzymes: the first inhibitors of GlcNAc-Ins deacetylase.,  50  (25): [PMID:18020307] [10.1021/jm070669h]

Source

Source(1):

• Scientific Literature