Altemicidin

Altemicidin

Names
IUPAC name (4aR,6S,7R,7aS)-4-carbamoyl-6-hydroxy-2-methyl-7-(2-sulfamoylacetamido)-2,4a,5,6,7,7a-hexahydro-1H-cyclopenta[c]pyridine-7-carboxylic acid
Identifiers
CAS Number	125399-82-8
3D model (JSmol)	Interactive image
ChemSpider	9211348
PubChem CID	11036174
UNII	39E2X82JVD^Y
CompTox Dashboard (EPA)	DTXSID20925120
InChI InChI=1S/C13H20N4O7S/c1-17-3-7(11(14)20)6-2-9(18)13(12(21)22,8(6)4-17)16-10(19)5-25(15,23)24/h3,6,8-9,18H,2,4-5H2,1H3,(H2,14,20)(H,16,19)(H,21,22)(H2,15,23,24)/t6-,8+,9-,13+/m0/s1 Key: VZRFZUPFQKSXPV-VPFIQFBESA-N InChI=1/C13H20N4O7S/c1-17-3-7(11(14)20)6-2-9(18)13(12(21)22,8(6)4-17)16-10(19)5-25(15,23)24/h3,6,8-9,18H,2,4-5H2,1H3,(H2,14,20)(H,16,19)(H,21,22)(H2,15,23,24)/t6-,8+,9-,13+/m0/s1 Key: VZRFZUPFQKSXPV-VPFIQFBEBF
SMILES O=S(=O)(N)CC(=O)N[C@@]2(C(=O)O)[C@@H](O)C[C@H]1C(=C/N(C[C@H]12)C)\C(=O)N
Properties
Chemical formula	C13H20N4O7S
Molar mass	376.39
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Altemicidin is monoterpene alkaloid first identified in isolates from marine actinomycetes (specifically Streptomyces sioyaensis) in 1989.[1][2] It may also be produced synthetically.[3][4] Altemicidin displays both acaricidal and antitumor activity.[1]

References

1. Takahashi, Atsushi; Kurasawa, Shogo; Ikeda, Daishiro; Okami, Yoshiro; Takeuchi, Tomio (1989). "Altemicidin, a new acaricidal and antitumor substance. I. Taxonomy, fermentation, isolation and physico-chemical and biological properties". The Journal of Antibiotics. 42 (11): 1556–1561. doi:10.7164/antibiotics.42.1556. ISSN 0021-8820. PMID 2584137.
2. Takahashi, Atsushi; Ikeda, Daishiro; Nakamura, Hikaru; Naganawa, Hiroshi; Kurasawa, Shogo; Okami, Yoshiro; Takeuchi, Tomio; Iitaka, Yoichi (1989). "Altemicidin, a new acaricidal and antitumor substance. II. Structure determination". The Journal of Antibiotics. 42 (11): 1562–1566. doi:10.7164/antibiotics.42.1562. ISSN 0021-8820. PMID 2584138.
3. Kende, Andrew S.; Liu, Kun; Jos Brands, K. M. (1995). "Total Synthesis of (-)-Altemicidin: A Novel Exploitation of the Potier-Polonovski Rearrangement". Journal of the American Chemical Society. 117 (42): 10597–10598. doi:10.1021/ja00147a032. ISSN 0002-7863.
4. Kan, Toshiyuki; Kawamoto, Yuichiro; Asakawa, Tomohiro; Furuta, Takumi; Fukuyama, Tohru (2008). "Synthetic Studies on Altemicidin: Stereocontrolled Construction of the Core Framework". Organic Letters. 10 (2): 169–171. doi:10.1021/ol701940f. ISSN 1523-7060. PMID 18081299.