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)-4-(dimethylamino)benzamide

ID: ALA232696

PubChem CID: 44430214

Max Phase: Preclinical

Molecular Formula: C22H34N2O10

Molecular Weight: 486.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1ccc(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)cc1

Standard InChI:  InChI=1S/C22H34N2O10/c1-24(2)12-5-3-11(4-6-12)20(31)23-16-19(30)18(29)15(9-25)34-21(16)33-14-8-22(32,10-26)7-13(27)17(14)28/h3-6,13-19,21,25-30,32H,7-10H2,1-2H3,(H,23,31)/t13-,14-,15-,16-,17-,18-,19-,21+,22+/m1/s1

Standard InChI Key:  KOOZSEHZHYHVDB-KYKWJYIFSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA232696

   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]-4-(dimethylamino)benzamide

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: 486.52

Molecular Weight (Monoisotopic): 486.2213

AlogP: -3.09

#Rotatable Bonds: 7

Polar Surface Area: 192.41

Molecular Species: NEUTRAL

HBA: 11

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.66

CX Basic pKa: 3.48

CX LogP: -3.26

CX LogD: -3.26

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.19

Np Likeness Score: 0.98

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