N-((2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-((1R,2R,3R,5S)-2,3,5-trihydroxy-5-(hydroxymethyl)cyclohexyloxy)-tetrahydro-2H-pyran-3-yl)-2-(propylthio)isonicotinamide

ID: ALA232305

PubChem CID: 44430221

Max Phase: Preclinical

Molecular Formula: C22H34N2O10S

Molecular Weight: 518.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCSc1cc(C(=O)N[C@H]2[C@@H](O[C@@H]3C[C@](O)(CO)C[C@@H](O)[C@H]3O)O[C@H](CO)[C@@H](O)[C@@H]2O)ccn1

Standard InChI:  InChI=1S/C22H34N2O10S/c1-2-5-35-15-6-11(3-4-23-15)20(31)24-16-19(30)18(29)14(9-25)34-21(16)33-13-8-22(32,10-26)7-12(27)17(13)28/h3-4,6,12-14,16-19,21,25-30,32H,2,5,7-10H2,1H3,(H,24,31)/t12-,13-,14-,16-,17-,18-,19-,21+,22+/m1/s1

Standard InChI Key:  NHUJYPSHKUFCAY-HQFKTWMZSA-N

Molfile:  

     RDKit          2D

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M  END

Alternative Forms

1. Parent:

   

   ALA232305

   N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(1R,2R,3R,5S)-2,3,5-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxyoxan-3-yl]-2-propylsulfanylpyridine-4-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: 518.59

Molecular Weight (Monoisotopic): 518.1934

AlogP: -2.25

#Rotatable Bonds: 9

Polar Surface Area: 202.06

Molecular Species: NEUTRAL

HBA: 12

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.64

CX Basic pKa: 1.79

CX LogP: -2.59

CX LogD: -2.59

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.16

Np Likeness Score: 0.76

References

1. Metaferia BB, Ray S, Smith JA, Bewley CA..  (2007)  Design and synthesis of substrate-mimic inhibitors of mycothiol-S-conjugate amidase from Mycobacterium tuberculosis.,  17  (2): [PMID:17084627] [10.1016/j.bmcl.2006.10.031]

Source

Source(1):

• Scientific Literature