4-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2S,3S)-3-((1S,2S)-2-hydroxy-1-methyl-propyl)-oxiranylmethyl]-tetrahydro-pyran-2-yl}-1-(4-methoxy-phenyl)-butane-1,3-dione

ID: ALA52826

Chembl Id: CHEMBL52826

PubChem CID: 44297817

Max Phase: Preclinical

Molecular Formula: C23H32O8

Molecular Weight: 436.50

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  COc1ccc(C(=O)CC(=O)C[C@@H]2OC[C@H](C[C@@H]3O[C@H]3[C@@H](C)[C@H](C)O)[C@@H](O)[C@H]2O)cc1

Standard InChI:  InChI=1S/C23H32O8/c1-12(13(2)24)23-20(31-23)8-15-11-30-19(22(28)21(15)27)10-16(25)9-18(26)14-4-6-17(29-3)7-5-14/h4-7,12-13,15,19-24,27-28H,8-11H2,1-3H3/t12-,13-,15-,19-,20-,21+,22-,23-/m0/s1

Standard InChI Key:  QSRZFUYBZRSSNF-PDUVUYJXSA-N

Associated Targets(Human)

IARS1 Tchem Isoleucyl-tRNA synthetase (99 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

ileS Isoleucyl-tRNA synthetase (49 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 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: 436.50Molecular Weight (Monoisotopic): 436.2097AlogP: 1.14#Rotatable Bonds: 10
Polar Surface Area: 125.82Molecular Species: NEUTRALHBA: 8HBD: 3
#RO5 Violations: HBA (Lipinski): 8HBD (Lipinski): 3#RO5 Violations (Lipinski):
CX Acidic pKa: 9.51CX Basic pKa: CX LogP: 0.69CX LogD: 0.69
Aromatic Rings: 1Heavy Atoms: 31QED Weighted: 0.28Np Likeness Score: 1.36

References

1. Bennett I, Broom NJ, Cassels R, Elder JS, Masson ND, O'Hanlon PJ..  (1999)  Synthesis and antibacterial properties of beta-diketone acrylate bioisosteres of pseudomonic acid A.,  (13): [PMID:10406653] [10.1016/s0960-894x(99)00296-6]

Source