Norzoanthamine

Norzoanthamine
IUPAC name (4aS,6aS,7S,7aS,9aS,11S,13R,15aR,16aS,16bR)- 1,4a,5,7,7a,8,9,11,12,13,14,16,16a,16b- Tetradecahydro-2,7,7a,11,16a- pentamethyl-4H,10H-9a,13-epoxy-15a,7-(epoxyethano) azepino[1,2-a]naphtho[2,1-g]quinoline-4,6,18(6aH)-trione
Other names Norzoanthamine
Identifiers
CAS number	164991-65-5
ChemSpider	10220837 Y
Jmol-3D images	Image 1
SMILES O=C2C[C@@H]1C(=O)/C=C(/C)C[C@H]1[C@]3(C)C[C@]47OC(=O)C[C@@](C)([C@@H]23)[C@]7(C)CC[C@@]65C[C@@H](C)C[C@H](CN45)O6
InChI InChI=1S/C29H39NO5/c1-16-9-20-19(21(31)10-16)11-22(32)24-25(20,3)15-29-27(5,26(24,4)13-23(33)35-29)6-7-28-12-17(2)8-18(34-28)14-30(28)29/h10,17-20,24H,6-9,11-15H2,1-5H3/t17-,18+,19-,20+,24-,25-,26-,27-,28-,29+/m0/s1 Y Key: RNNGFZNWONBXEI-JHPOJCJNSA-N Y InChI=1/C29H39NO5/c1-16-9-20-19(21(31)10-16)11-22(32)24-25(20,3)15-29-27(5,26(24,4)13-23(33)35-29)6-7-28-12-17(2)8-18(34-28)14-30(28)29/h10,17-20,24H,6-9,11-15H2,1-5H3/t17-,18+,19-,20+,24-,25-,26-,27-,28-,29+/m0/s1 Key: RNNGFZNWONBXEI-JHPOJCJNBZ
Properties
Molecular formula	C29H39NO5
Molar mass	481.62
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Norzoanthamine is a new alkaloid found in Zoanthus species (Class Anthozoa), a kind of sea anemones.

Norzoanthamine has been shown to suppress the loss of bone weight and strength in mice; that could lead to a treatment for osteoporosis. Some derivatives of norzoanthamine also suppress development of some kind of leukemia cell lines and human platelet aggregation.

A laboratory synthesis of this compound was developed in 2004.^[1]

References

1. ^ Masaaki Miyashita, Minoru Sasaki, Izumi Hattori, Mio Sakai, Keiji Tanino. "Total Synthesis of Norzoanthamine" Science 23 July 2004: Vol. 305. no. 5683, pp. 495 - 499 doi:10.1126/science.1098851