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

ID: ALA83449

Chembl Id: CHEMBL83449

PubChem CID: 10716206

Max Phase: Preclinical

Molecular Formula: C20H28N4O5

Molecular Weight: 404.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]([C@@H]1O[C@H]1C[C@H]1CO[C@@H](Cn2nnc(-c3ccccc3)n2)[C@H](O)[C@@H]1O)[C@H](C)O

Standard InChI:  InChI=1S/C20H28N4O5/c1-11(12(2)25)19-15(29-19)8-14-10-28-16(18(27)17(14)26)9-24-22-20(21-23-24)13-6-4-3-5-7-13/h3-7,11-12,14-19,25-27H,8-10H2,1-2H3/t11-,12-,14-,15-,16-,17+,18-,19-/m0/s1

Standard InChI Key:  QSAQNSJARHVGPL-VOJRGRSSSA-N

Alternative Forms

1. Parent:

   

   ALA83449

   (2S,3R,4R,5S)-5-[[(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl]-2-[(5-phenyltetrazol-2-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: 404.47

Molecular Weight (Monoisotopic): 404.2060

AlogP: 0.25

#Rotatable Bonds: 7

Polar Surface Area: 126.05

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.07

CX Basic pKa: ┄

CX LogP: 1.06

CX LogD: 1.06

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.56

Np Likeness Score: 0.35

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