ID: ALA3989485

Max Phase: Phase

Molecular Formula: C22H34O5

Molecular Weight: 378.51

Molecule Type: Small molecule

Representations

Synonyms (6): Antibiotic a 40104c | Drosophilin b | Mutilin 14-glycolate | Pleuromutilin | BC-757 | NSC-121145
Synonyms from Alternative Forms(6):

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-BKUNHTPHSA-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: Yes

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. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

2. Gao ML, Zeng J, Fang X, Luo J, Jin Z, Liu YH, Tang YZ..  (2017)  Design, synthesis and antibacterial evaluation of novel pleuromutilin derivatives possessing piperazine linker.,  127  [PMID:28068600] [10.1016/j.ejmech.2017.01.004]

3. Jacobs RT, Lunde CS, Freund YR, Hernandez V, Li X, Xia Y, Carter DS, Berry PW, Halladay J, Rock F, Stefanakis R, Easom E, Plattner JJ, Ford L, Johnston KL, Cook DAN, Clare R, Cassidy A, Myhill L, Tyrer H, Gamble J, Guimaraes AF, Steven A, Lenz F, Ehrens A, Frohberger SJ, Koschel M, Hoerauf A, Hübner MP, McNamara CW, Bakowski MA, Turner JD, Taylor MJ, Ward SA..  (2019)  Boron-Pleuromutilins as Anti- Wolbachia Agents with Potential for Treatment of Onchocerciasis and Lymphatic Filariasis.,  62  (5): [PMID:30730745] [10.1021/acs.jmedchem.8b01854]

4. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of University of Manchester (UK) compounds,  [10.6019/CHEMBL4513137]

5. Zhang Z,Li K,Zhang GY,Tang YZ,Jin Z.  (2020)  Design, synthesis and biological activities of novel pleuromutilin derivatives with a substituted triazole moiety as potent antibacterial agents.,  204  [PMID:32731187] [10.1016/j.ejmech.2020.112604]

6. Li B, Zhang Z, Zhang JF, Liu J, Zuo XY, Chen F, Zhang GY, Fang HQ, Jin Z, Tang YZ..  (2021)  Design, synthesis and biological evaluation of pleuromutilin-Schiff base hybrids as potent anti-MRSA agents in vitro and in vivo.,  223  [PMID:34153574] [10.1016/j.ejmech.2021.113624]

7. Zhang K, Song W, Wei M, Sun Y, Wang N, Ma L, Yu X, Gao R, Wang R, Zhang Y, Zheng N, Li N, Mu L, Tang Z, Li X, Yang C, Yang G..  (2021)  A Novel Anticancer Stem Cell Compound Derived from Pleuromutilin Induced Necroptosis of Melanoma Cells.,  64  (21.0): [PMID:34704758] [10.1021/acs.jmedchem.1c01123]

8. Zhang K, Liang J, Wang N, Li N, Jiang Y, Li X, Yang C, Zhou H, Yang G..  (2022)  Discovery of a novel Pleuromutilin derivative as anti-IPF lead compound via high-throughput assay.,  241  [PMID:35961069] [10.1016/j.ejmech.2022.114643]

9. Wu G, Zhu Z, Li J, Luo X, Zhu W, Liao G, Xia J, Zhang W, Pan W, Li T, Wu S..  (2022)  Design, synthesis and antibacterial evaluation of pleuromutilin derivatives.,  59  [PMID:35220163] [10.1016/j.bmc.2022.116676]

Source

Source(3):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names
• CO-ADD antimicrobial screening data