2-(4-chlorophenylthio)-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)nicotinamide

ID: ALA232506

PubChem CID: 44430222

Max Phase: Preclinical

Molecular Formula: C25H31ClN2O10S

Molecular Weight: 587.05

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)c1cccnc1Sc1ccc(Cl)cc1

Standard InChI:  InChI=1S/C25H31ClN2O10S/c26-12-3-5-13(6-4-12)39-23-14(2-1-7-27-23)22(35)28-18-21(34)20(33)17(10-29)38-24(18)37-16-9-25(36,11-30)8-15(31)19(16)32/h1-7,15-21,24,29-34,36H,8-11H2,(H,28,35)/t15-,16-,17-,18-,19-,20-,21-,24+,25+/m1/s1

Standard InChI Key:  NBGKDOCFVBSLCH-ZWMLVRTDSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA232506

   2-(4-chlorophenyl)sulfanyl-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]pyridine-3-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: 587.05

Molecular Weight (Monoisotopic): 586.1388

AlogP: -0.95

#Rotatable Bonds: 8

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: 12.58

CX Basic pKa: 2.62

CX LogP: -1.20

CX LogD: -1.20

Aromatic Rings: 2

Heavy Atoms: 39

QED Weighted: 0.19

Np Likeness Score: 0.42

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