(2S,3R,4R,5S)-5-[(2S,3S)-3-((1S,2S)-2-Hydroxy-1-methyl-propyl)-oxiranylmethyl]-2-(2-phenyl-oxazol-5-ylmethyl)-tetrahydro-pyran-3,4-diol

ID: ALA276855

Chembl Id: CHEMBL276855

PubChem CID: 10644853

Max Phase: Preclinical

Molecular Formula: C22H29NO6

Molecular Weight: 403.48

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  C[C@H]([C@@H]1O[C@H]1C[C@H]1CO[C@@H](Cc2cnc(-c3ccccc3)o2)[C@H](O)[C@@H]1O)[C@H](C)O

Standard InChI:  InChI=1S/C22H29NO6/c1-12(13(2)24)21-18(29-21)8-15-11-27-17(20(26)19(15)25)9-16-10-23-22(28-16)14-6-4-3-5-7-14/h3-7,10,12-13,15,17-21,24-26H,8-9,11H2,1-2H3/t12-,13-,15-,17-,18-,19+,20-,21-/m0/s1

Standard InChI Key:  GFUGDROARRTBDR-ZVRIMKIWSA-N

Associated Targets(non-human)

ileS Isoleucyl-tRNA synthetase (49 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus aureus (210822 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 403.48Molecular Weight (Monoisotopic): 403.1995AlogP: 1.80#Rotatable Bonds: 7
Polar Surface Area: 108.48Molecular Species: NEUTRALHBA: 7HBD: 3
#RO5 Violations: HBA (Lipinski): 7HBD (Lipinski): 3#RO5 Violations (Lipinski):
CX Acidic pKa: 13.10CX Basic pKa: 0.97CX LogP: 0.83CX LogD: 0.83
Aromatic Rings: 2Heavy Atoms: 29QED Weighted: 0.61Np Likeness Score: 1.08

References

1. Brown P, Best DJ, Broom NJ, Cassels R, O'Hanlon PJ, Mitchell TJ, Osborne NF, Wilson JM..  (1997)  The chemistry of pseudomonic acid. 18. Heterocyclic replacement of the alpha,beta-unsaturated ester: synthesis, molecular modeling, and antibacterial activity.,  40  (16): [PMID:9258363] [10.1021/jm960738k]

Source