Globoidnan A

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Globoidnan A

IUPAC name (2R)-(3,4-dihydroxyphenyl)-2-{[4-(3,4-dihydroxyphenyl)-6,7-dihydroxy-2-naphthoyl]oxy}propanoic acid
Identifiers
CAS number	827322-48-5^Y
PubChem	3013628
ChemSpider	26333277^N
Jmol-3D images	{{#if:c1cc(c(cc1C[C@H](C(=O)O)OC(=O)c2cc3cc(c(cc3c(c2)c4ccc(c(c4)O)O)O)O)O)O\|Image 1
SMILES c1cc(c(cc1C[C@H](C(=O)O)OC(=O)c2cc3cc(c(cc3c(c2)c4ccc(c(c4)O)O)O)O)O)O
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/s1^N Key: DHZIDIIBBCIIEG-XMMPIXPASA-N^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/s1 Key: DHZIDIIBBCIIEG-XMMPIXPABS
Properties
Molecular formula	C₂₆H₂₀O₁₀
Molar mass	492.43 g mol⁻¹
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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

The molecule has been found to inhibit the action of HIV integrase,^[1] 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.

Antiviral drugs: antiretroviral drugs used against HIV (primarily J05)

Entry/fusion inhibitors
(Discovery & development)

gp41 (Enfuvirtide)
CCR5 (Maraviroc
Vicriviroc^†, Cenicriviroc^†, PRO 140^†)
CD4 (Ibalizumab^†)

Reverse-transcriptase
inhibitors (RTIs)

Nucleoside & nucleotide (NRTI)	Nucleoside analogues/NARTIs: Abacavir (ABC)°^# Emtricitabine (FTC)°^# Lamivudine (3TC)°^# Didanosine (ddI)^# Zidovudine (AZT)^# Apricitabine^† Stampidine^† Elvucitabine^† Racivir^† Amdoxovir^† Stavudine (d4T)^# Zalcitabine (ddC)^◊ Festinavir^† Nucleotide analogues/NtRTIs: Tenofovir disoproxil fumarate (TDF)°^# Tenofovir alafenamide fumarate (TAF)^†

Non-nucleoside (NNRTI) (Discovery & development)	(1st generation) Efavirenz (EFV)°^# Nevirapine (NVP)^# Loviride^◊ Delavirdine (DLV)^◊ (2nd generation) diarylpyrimidines (Etravirine Rilpivirine) Lersivirine^†

Integrase inhibitors

Maturation inhibitors

Bevirimat^†

Protease Inhibitors (PI)
(Discovery and development)

1st generation	Fosamprenavir° Lopinavir°^# Nelfinavir^# Ritonavir^# Saquinavir^# Amprenavir^◊ Indinavir^◊^#

2nd generation	Atazanavir° Darunavir° Tipranavir

Combined formulations

Experimental agents

Uncoating inhibitors	TRIM5alpha (gene)

Transcription inhibitors	Tat antagonists

Translation inhibitors	Trichosanthin

Other	Abzyme Calanolide A Ceragenin Cyanovirin-N Diarylpyrimidines Epigallocatechin gallate (EGCG) Foscarnet Griffithsin Hydroxycarbamide Miltefosine Portmanteau inhibitors Seliciclib^† Synergistic enhancers Tre recombinase Zinc finger protein transcription factor KP-1461^† Cobicistat^†

Failed agents	Dexelvucitabine Capravirine Emivirine Lodenosine Atevirdine Brecanavir Aplaviroc

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

°DHHS preferred first-line agent. ^◊Formerly or rarely used agent.

M: VIR

virs(prot)/clss

cutn/syst (hppv/hiva, infl/zost/zoon)/epon

drug (dnaa, rnaa, rtva, vacc)

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

Mammalian lignans (enterolignans)	Enterodiol Enterolactone Lariciresinol Hydroxymatairesinol Syringaresinol

Neolignans	Balanophonin Eusiderin Honokiol 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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