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

ID: ALA312853

Chembl Id: CHEMBL312853

PubChem CID: 10501347

Max Phase: Preclinical

Molecular Formula: C22H29NO6

Molecular Weight: 403.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]([C@@H]1O[C@H]1C[C@H]1CO[C@@H](Cc2cc(-c3ccccc3)no2)[C@H](O)[C@@H]1O)[C@H](C)O

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

Standard InChI Key:  XHYWZPXUTMEBMX-MRQXEPQISA-N

Alternative Forms

1. Parent:

   

   ALA312853

   (2S,3R,4R,5S)-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]-2-[(3-phenyl-1,2-oxazol-5-yl)methyl]oxane-3,4-diol

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: 403.48

Molecular Weight (Monoisotopic): 403.1995

AlogP: 1.80

#Rotatable Bonds: 7

Polar Surface Area: 108.48

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.10

CX Basic pKa: 0.41

CX LogP: 1.26

CX LogD: 1.26

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.61

Np Likeness Score: 0.79

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

Source(1):

• Scientific Literature