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-(trifluoromethyl)benzamide

ID: ALA399182

PubChem CID: 44430217

Max Phase: Preclinical

Molecular Formula: C21H28F3NO10

Molecular Weight: 511.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@H]1[C@@H](O[C@@H]2C[C@](O)(CO)C[C@@H](O)[C@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O)c1ccc(C(F)(F)F)cc1

Standard InChI:  InChI=1S/C21H28F3NO10/c22-21(23,24)10-3-1-9(2-4-10)18(32)25-14-17(31)16(30)13(7-26)35-19(14)34-12-6-20(33,8-27)5-11(28)15(12)29/h1-4,11-17,19,26-31,33H,5-8H2,(H,25,32)/t11-,12-,13-,14-,15-,16-,17-,19+,20+/m1/s1

Standard InChI Key:  UOOZEHZTBOTQJV-JHBMTMDISA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA399182

   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-(trifluoromethyl)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: 511.45

Molecular Weight (Monoisotopic): 511.1665

AlogP: -2.13

#Rotatable Bonds: 6

Polar Surface Area: 189.17

Molecular Species: NEUTRAL

HBA: 10

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.66

CX Basic pKa: ┄

CX LogP: -2.49

CX LogD: -2.49

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.21

Np Likeness Score: 0.90

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