Psoromic acid

Psoromic acid is a β-orcinol depsidone with the molecular formula C₁₈H₁₄O₈. Psoromic acid inhibits herpes simplex viruses type 1 and type 2.^[2] Furthermore, it inhibits the RabGGTase.^[3] Psoromic acid occurs in antarctic lichens.^[2][4]

Psoromic acid

Names
IUPAC name 10-Formyl-9-hydroxy-3-methoxy-4,7-dimethyl-6-oxobenzo[b][1,4]benzodioxepine-1-carboxylic acid^[1]
Other names 4-Formyl-3-hydroxy-8-methoxy-1,9-dimethyl-11-oxo-11H-dibenzo[b,e][1,4]dioxepin-6-carboxylic acid Parellic acid NSC 92186
Identifiers
CAS Number	7299-11-8^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:92074
ChEMBL	ChEMBL176570
ChemSpider	22185
PubChem CID	23725
CompTox Dashboard (EPA)	DTXSID70223264
InChI InChI=1S/C18H14O8/c1-7-4-11(20)10(6-19)15-13(7)18(23)26-14-8(2)12(24-3)5-9(17(21)22)16(14)25-15/h4-6,20H,1-3H3,(H,21,22) Key: FUCWJKJZOHOLEO-UHFFFAOYSA-N
SMILES CC1=C(OC)C=C(C(O)=O)C(OC2=C3C(C)=CC(O)=C2C=O)=C1OC3=O
Properties
Chemical formula	C18H14O8
Molar mass	358.302 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

References

1. "Psoromic acid". Pubchem.ncbi.NLM.nih.gov.
2. Hassan, Sherif T. S.; Šudomová, Miroslava; Berchová-Bímová, Kateřina; Šmejkal, Karel; Echeverría, Javier (11 August 2019). "Psoromic Acid, a Lichen-Derived Molecule, Inhibits the Replication of HSV-1 and HSV-2, and Inactivates HSV-1 DNA Polymerase: Shedding Light on Antiherpetic Properties". Molecules. 24 (16): 2912. doi:10.3390/molecules24162912. PMC 6720901. PMID 31405197.
3. Deraeve, Céline; Guo, Zhong; Bon, Robin S.; Blankenfeldt, Wulf; DiLucrezia, Raffaella; Wolf, Alexander; Menninger, Sascha; Stigter, E. Anouk; Wetzel, Stefan; Choidas, Axel; Alexandrov, Kirill; Waldmann, Herbert; Goody, Roger S.; Wu, Yao-Wen (2 May 2012). "Psoromic Acid is a Selective and Covalent Rab-Prenylation Inhibitor Targeting Autoinhibited RabGGTase". Journal of the American Chemical Society. 134 (17): 7384–7391. doi:10.1021/ja211305j. PMID 22480322.
4. Sukumaran, Swapna Thacheril; Sugathan, Shiburaj; Abdulhameed, Sabu (28 November 2020). Plant Metabolites: Methods, Applications and Prospects. Springer Nature. p. 278. ISBN 978-981-15-5136-9.

Further reading

• Deraeve, Céline; Guo, Zhong; Bon, Robin S.; Blankenfeldt, Wulf; DiLucrezia, Raffaella; Wolf, Alexander; Menninger, Sascha; Stigter, E. Anouk; Wetzel, Stefan; Choidas, Axel; Alexandrov, Kirill; Waldmann, Herbert; Goody, Roger S.; Wu, Yao-Wen (2 May 2012). "Psoromic Acid is a Selective and Covalent Rab-Prenylation Inhibitor Targeting Autoinhibited RabGGTase". Journal of the American Chemical Society. 134 (17): 7384–7391. doi:10.1021/ja211305j. PMID 22480322.
• Der Stoffwechsel Sekundärer Pflanzenstoffe / The Metabolism of Secondary Plant Products. Springer Science & Business Media. 11 November 2013. p. 592. ISBN 978-3-662-26784-4.
• Year-book of Pharmacy. J. & A. Churchill. 1883. p. 246.
• Issues in Chemistry and General Chemical Research: 2013 Edition. ScholarlyEditions. 1 May 2013. p. 323. ISBN 978-1-4901-0631-1.