Aphidicolin

Aphidicolin

Names
IUPAC name (3R,4R,4aR,6aS,8R,9R,11aS,11bS)-4,9-bis(hydroxymethyl)-4,11b-dimethyltetradecahydro-8,11a-methanocyclohepta[a]naphthalene-3,9-diol
Identifiers
CAS Number	38966-21-1^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:2766^N
ChEMBL	ChEMBL29711^Y
ChemSpider	10280269^Y
ECHA InfoCard	100.109.656
PubChem CID	457964
UNII	192TJ6PP19^Y
CompTox Dashboard (EPA)	DTXSID5036711
InChI InChI=1S/C20H34O4/c1-17(11-21)15-4-3-13-9-14-10-19(13,7-8-20(14,24)12-22)18(15,2)6-5-16(17)23/h13-16,21-24H,3-12H2,1-2H3/t13-,14+,15-,16+,17-,18-,19-,20-/m0/s1^Y Key: NOFOAYPPHIUXJR-APNQCZIXSA-N^Y InChI=1/C20H34O4/c1-17(11-21)15-4-3-13-9-14-10-19(13,7-8-20(14,24)12-22)18(15,2)6-5-16(17)23/h13-16,21-24H,3-12H2,1-2H3/t13-,14+,15-,16+,17-,18-,19-,20-/m0/s1 Key: NOFOAYPPHIUXJR-APNQCZIXBU
SMILES OC[C@@]4(O)CC[C@]31C[C@H]4C[C@@H]3CC[C@H]2[C@](C)(CO)[C@H](O)CC[C@]12C
Properties
Chemical formula	C20H34O4
Molar mass	338.48 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Aphidicolin is a tetracyclic diterpene antibiotic isolated from the fungus Cephalosporum aphidicola with antiviral and antimitotic properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication. It blocks the cell cycle at early S phase. It is a specific inhibitor of DNA polymerase Alpha and Delta in eukaryotic cells and in some viruses (vaccinia^[1][2] and herpesviruses) and an apoptosis inducer in HeLa cells. Natural aphidicolin is a secondary metabolite of the fungus Nigrospora oryzae.^[3]

Bibliography

• Dhillon VS, Husain SA, Ray GN (2003). "Expression of aphidicolin-induced fragile sites and their relationship between genetic susceptibility in breast cancer, ovarian cancer, and non-small-cell lung cancer patients". Teratogenesis, Carcinogenesis, and Mutagenesis. Suppl 1: 35–45. doi:10.1002/tcm.10068. PMID 12616595.
• Mahy, Brian W J (2001). A dictionary of virology (3. ed.). San Diego, Calif. [u.a.]: Academic Press. p. 19. ISBN 978-0-12-465327-6.

References

1. DeFilippes, FM (Nov 1984). "Effect of aphidicolin on vaccinia virus: isolation of an aphidicolin-resistant mutant". Journal of Virology. 52 (2): 474–82. doi:10.1128/JVI.52.2.474-482.1984. PMC 254548. PMID 6436508.
2. Bucknall, R. A.; Moores, H.; Simms, R.; Hesp, B. (1 September 1973). "Antiviral Effects of Aphidicolin, a New Antibiotic Produced by Cephalosporium aphidicola". Antimicrobial Agents and Chemotherapy. 4 (3): 294–298. doi:10.1128/AAC.4.3.294. PMC 444544. PMID 4357181.
3. Aphidicolin product page Archived June 26, 2006, at the Wayback Machine from Fermentek