Globoidnan A - Misplaced Pages

Globoidnan A
Names

Preferred IUPAC name (2R)-3-(3,4-Dihydroxyphenyl)-2-{oxy}propanoic acid
Identifiers
CAS Number	827322-48-5
3D model (JSmol)	Interactive image
ChemSpider	26333277
PubChem CID	3013628
UNII	8UFJ4K6MGW
CompTox Dashboard (EPA)	DTXSID60895853
InChI InChI=1S/C26H20O10/c27-18-3-1-12(5-20(18)29)6-24(25(33)34)36-26(35)15-7-14-10-22(31)23(32)11-17(14)16(8-15)13-2-4-19(28)21(30)9-13/h1-5,7-11,24,27-32H,6H2,(H,33,34)/t24-/m1/s1Key: DHZIDIIBBCIIEG-XMMPIXPASA-N InChI=1/C26H20O10/c27-18-3-1-12(5-20(18)29)6-24(25(33)34)36-26(35)15-7-14-10-22(31)23(32)11-17(14)16(8-15)13-2-4-19(28)21(30)9-13/h1-5,7-11,24,27-32H,6H2,(H,33,34)/t24-/m1/s1Key: DHZIDIIBBCIIEG-XMMPIXPABS
SMILES c1cc(c(cc1C(C(=O)O)OC(=O)c2cc3cc(c(cc3c(c2)c4ccc(c(c4)O)O)O)O)O)O
Properties
Chemical formula	C₂₆H₂₀O₁₀
Molar mass	492.436 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Globoidnan A is a lignan found in Eucalyptus globoidea, a tree native to Australia.

The molecule has been found to weakly inhibit the action of HIV integrase (IC₅₀ = 0.64 μM) in vitro. HIV integrase is an enzyme which is responsible for the introduction of HIV viral DNA into a host's cellular DNA. It is not known that globoidnan A inhibits the action of other retroviral integrases.

References

Ovenden SP, Yu J, Wan SS, et al. (2004). "Globoidnan A: a lignan from Eucalyptus globoidea inhibits HIV integrase". Phytochemistry. 65 (24): 3255–59. doi:10.1016/j.phytochem.2004.10.006. PMID 15561191.

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v t e Types of lignans
Lignans	Arboreol Arctigenin Chamaecypanone A and B Eudesmin Globoidnan A Gmelanone Gmelinol Gummadiol Isootobanone Lyoniresinol Macelignan Matairesinol Obtulignolide Pinoresinol Pluviatilol Podophyllotoxin Secoisolariciresinol Sesamin Sesamolin Steganacin
Lignan glycosides	Arctiin Aviculin (isolariciresinol-9'-rhamnopyranoside) Secoisolariciresinol diglucoside (SDG)
Mammalian lignans (enterolignans)	Enterodiol Enterolactone Lariciresinol Hydroxymatairesinol Syringaresinol
Neolignans	Balanophonin Eusiderin Honokiol Interiotherin Linderin A Magnolol Megaphone 4-O-Methylhonokiol Rhaphidecursinol A Rhaphidecursinol B
Flavonolignans	Cinchonain-Ib Dehydrosilybin Deoxysilycistin Deoxysilydianin Hydnocarpin Hydnowightin Neosilyhermin Palstatin Rhodiolin Salcolin A Salcolin B Scutellaprostin A, B, C, D, E and F Silandrin Silyamandin Silibinin Silybinome Silicristin Silydianin Silyhermin Tricin 4'-O-(erythro-beta-guaiacylglyceryl) ether Tricin 4'-O-(threo-beta-guaiacylglyceryl) ether

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