ID: ALA497295

Max Phase: Preclinical

Molecular Formula: C22H34O5

Molecular Weight: 378.51

Molecule Type: Small molecule

Representations

Synonyms (1): Pleuromutilin
Synonyms from Alternative Forms(1):

Canonical SMILES:  C=C[C@]1(C)C[C@@H](OC(=O)CO)[C@]2(C)[C@H](C)CC[C@]3(CCC(=O)[C@@H]32)[C@@H](C)[C@@H]1O

Standard InChI:  InChI=1S/C22H34O5/c1-6-20(4)11-16(27-17(25)12-23)21(5)13(2)7-9-22(14(3)19(20)26)10-8-15(24)18(21)22/h6,13-14,16,18-19,23,26H,1,7-12H2,2-5H3/t13-,14+,16-,18-,19+,20-,21+,22+/m1/s1

Standard InChI Key:  ZRZNJUXESFHSIO-BWQWJNJNSA-N

Molecule Features

Natural Product: Yes

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

Properties

Molecular Weight: 378.51

Molecular Weight (Monoisotopic): 378.2406

AlogP: 2.89

#Rotatable Bonds: 3

Polar Surface Area: 83.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.11

CX Basic pKa:

CX LogP: 2.60

CX LogD: 2.60

Aromatic Rings: 0

Heavy Atoms: 27

QED Weighted: 0.58

Np Likeness Score: 2.64

References

1. Springer DM, Bunker A, Luh BY, Sorenson ME, Goodrich JT, Bronson JJ, DenBleyker K, Dougherty TJ, Fung-Tomc J..  (2007)  Cyclopentanone ring-cleaved pleuromutilin derivatives.,  42  (1): [PMID:17156897] [10.1016/j.ejmech.2006.07.018]

2. Lolk L, Pøhlsgaard J, Jepsen AS, Hansen LH, Nielsen H, Steffansen SI, Sparving L, Nielsen AB, Vester B, Nielsen P..  (2008)  A click chemistry approach to pleuromutilin conjugates with nucleosides or acyclic nucleoside derivatives and their binding to the bacterial ribosome.,  51  (16): [PMID:18680270] [10.1021/jm800261u]

3. Dreier I, Kumar S, Søndergaard H, Rasmussen ML, Hansen LH, List NH, Kongsted J, Vester B, Nielsen P..  (2012)  A click chemistry approach to pleuromutilin derivatives, part 2: conjugates with acyclic nucleosides and their ribosomal binding and antibacterial activity.,  55  (5): [PMID:22280300] [10.1021/jm201266b]

4. Dreier I, Hansen LH, Nielsen P, Vester B..  (2014)  A click chemistry approach to pleuromutilin derivatives. Part 3: extended footprinting analysis and excellent MRSA inhibition for a derivative with an adenine phenyl side chain.,  24  (4): [PMID:24486133] [10.1016/j.bmcl.2014.01.019]

Source

Source(1):

• Scientific Literature