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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H26O12
Molecular Weight 470.4239
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PLUMIERIDE

SMILES

[H][C@]12C=C[C@]3(OC(=O)C(=C3)[C@H](C)O)[C@@]1([H])[C@H](O[C@]4([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)OC=C2C(=O)OC

InChI

InChIKey=AOPMSFXOYJXDNJ-IRFSQMTFSA-N
InChI=1S/C21H26O12/c1-8(23)10-5-21(33-18(10)28)4-3-9-11(17(27)29-2)7-30-19(13(9)21)32-20-16(26)15(25)14(24)12(6-22)31-20/h3-5,7-9,12-16,19-20,22-26H,6H2,1-2H3/t8-,9+,12+,13+,14+,15-,16+,19-,20-,21+/m0/s1

HIDE SMILES / InChI

Molecular Formula C21H26O12
Molecular Weight 470.4239
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12112301 | https://www.ncbi.nlm.nih.gov/pubmed/25888719

Plumieride was isolated as one of the major components from the biologically active methanolic extract of the bark of Plumeria bicolor (family Apocynaceae). It possess antifungal and moderate cytotoxic effect, and demonstrates anti-malarial activity in vivo.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Cytotoxic constituents of the bark of Plumeria rubra collected in Indonesia.
1990 Nov-Dec
HIV-1 and HIV-2 reverse transcriptases: a comparative study of sensitivity to inhibition by selected natural products.
1992 May 29
Plumieride from Allamanda cathartica as an antidermatophytic agent.
2002 Jun
Structural modifications of plumieride isolated from Plumeria bicolor and the effect of these modifications on in vitro anticancer activity.
2004 Sep 17
Anti-malarial activity and toxicity assessment of Himatanthus articulatus, a plant used to treat malaria in the Brazilian Amazon.
2015 Mar 27
Patents

Sample Use Guides

In toxicology experiments, plumieride was fed to male rats orally at doses of (15 mg/rat/day) for the period of 60 days.
Route of Administration: Oral
For anti-fungal experiment, 5 mg of of the plumieride was dissolved in 10 mL of 50% ethanol. The assay disc was impregnated with 2mL of the solution of compound prepared in 50% ethanol by repeated addition and evaporation of the solvent. For the control, discs were impregnated with 50% ethanol. The assay discs were transferred aseptically to the Petri plates containing Sabouraud dextrose agar medium. The plates were inoculated separately by the mycelial disc of the test dermatophytes, Epidermophyton floccosum and Microsporum gypseum. The plates were incubated at 28°1°C for 6 days and the colony diameter of the test dermatophytes of the treatment and control sets were measured on day 7 and the per cent inhibition of growth of test dermatophytes was calculated.
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:23:16 GMT 2023
Edited
by admin
on Sat Dec 16 08:23:16 GMT 2023
Record UNII
71A048XW8V
Record Status Validated (UNII)
Record Version
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Name Type Language
PLUMIERIDE
MI  
Common Name English
SPIRO(CYCLOPENTA(C)PYRAN-7(1H),2'(5'H)-FURAN)-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-4A,7A-DIHYDRO-4'-((1S)-1-HYDROXYETHYL)-5'-OXO-, METHYL ESTER, (1S,2'R,4AS,7AS)-
Systematic Name English
PLUMIERIDE [MI]
Common Name English
(1S,2R,4AS,7AS)-1-(.BETA.-D-GLUCOPYRANOSYLOXY)-4A,7A-DIHYDRO-4-((1S)-1-HYDROXYETHYL)-5-OXOSPIRO(CYCLOPENTA(C)PYRAN-7(1H),2(5H)-FURAN)-4-CARBOXYLIC ACID METHYL ESTER
Systematic Name English
AGONIADIN
Common Name English
NSC-609065
Code English
Code System Code Type Description
MERCK INDEX
m8927
Created by admin on Sat Dec 16 08:23:16 GMT 2023 , Edited by admin on Sat Dec 16 08:23:16 GMT 2023
PRIMARY Merck Index
PUBCHEM
72319
Created by admin on Sat Dec 16 08:23:16 GMT 2023 , Edited by admin on Sat Dec 16 08:23:16 GMT 2023
PRIMARY
EPA CompTox
DTXSID40199109
Created by admin on Sat Dec 16 08:23:16 GMT 2023 , Edited by admin on Sat Dec 16 08:23:16 GMT 2023
PRIMARY
NSC
609065
Created by admin on Sat Dec 16 08:23:16 GMT 2023 , Edited by admin on Sat Dec 16 08:23:16 GMT 2023
PRIMARY
CAS
511-89-7
Created by admin on Sat Dec 16 08:23:16 GMT 2023 , Edited by admin on Sat Dec 16 08:23:16 GMT 2023
PRIMARY
FDA UNII
71A048XW8V
Created by admin on Sat Dec 16 08:23:16 GMT 2023 , Edited by admin on Sat Dec 16 08:23:16 GMT 2023
PRIMARY