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)benzo[b]thiophene-6-carboxamide

ID: ALA232304

PubChem CID: 44430219

Max Phase: Preclinical

Molecular Formula: C22H29NO10S

Molecular Weight: 499.54

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)c1ccc2ccsc2c1

Standard InChI:  InChI=1S/C22H29NO10S/c24-8-14-18(28)19(29)16(23-20(30)11-2-1-10-3-4-34-15(10)5-11)21(33-14)32-13-7-22(31,9-25)6-12(26)17(13)27/h1-5,12-14,16-19,21,24-29,31H,6-9H2,(H,23,30)/t12-,13-,14-,16-,17-,18-,19-,21+,22+/m1/s1

Standard InChI Key:  CUTDHBJABDXNJX-HQFKTWMZSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA232304

   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]-1-benzothiophene-6-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: 499.54

Molecular Weight (Monoisotopic): 499.1512

AlogP: -1.94

#Rotatable Bonds: 6

Polar Surface Area: 189.17

Molecular Species: NEUTRAL

HBA: 11

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.66

CX Basic pKa: ┄

CX LogP: -2.50

CX LogD: -2.50

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.22

Np Likeness Score: 0.84

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