amarogentin (Q3613679)

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chemical compound

(4aS,5R,6S)-5-ethenyl-1-oxo-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl- 2-O-[(3,3',5-trihydroxybiphenyl-2-yl)carbonyl]-beta-D-glucopyranoside
sweroside-2'-(3'',5'',3'''-trihydroxydiphenyl)-2''-carboxylic acid ester

Language	Label	Description	Also known as
English	amarogentin	chemical compound	(4aS,5R,6S)-5-ethenyl-1-oxo-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl- 2-O-[(3,3',5-trihydroxybiphenyl-2-yl)carbonyl]-beta-D-glucopyranoside sweroside-2'-(3'',5'',3'''-trihydroxydiphenyl)-2''-carboxylic acid ester

Statements

type of chemical entity

0 references

secoiridoid monoterpenoid

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chemical structure

Amarogentin.png
1,375 × 1,145; 10 KB

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586.168641 dalton

1 reference

language of work or name

sweroside-2'-(3'',5'',3'''-trihydroxydiphenyl)-2''-carboxylic acid ester (English)

5 October 2016

stereoisomer of

[(2S,3R,4R,5S,6R)-2-[[(3R,4R,4aS)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate

2 references

based on heuristic

inferred from InChIKey

based on heuristic

inferred from InChI

chemical formula

C₂₉H₃₀O₁₃

1 reference

language of work or name

sweroside-2'-(3'',5'',3'''-trihydroxydiphenyl)-2''-carboxylic acid ester (English)

5 October 2016

canonical SMILES

C=CC1C2CCOC(=O)C2=COC1OC3C(C(C(C(O3)CO)O)O)OC(=O)C4=C(C=C(C=C4C5=CC(=CC=C5)O)O)O

1 reference

language of work or name

sweroside-2'-(3'',5'',3'''-trihydroxydiphenyl)-2''-carboxylic acid ester (English)

5 October 2016

isomeric SMILES

C=C[C@@H]1[C@@H]2CCOC(=O)C2=CO[C@H]1O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)OC(=O)C4=C(C=C(C=C4C5=CC(=CC=C5)O)O)O

1 reference

language of work or name

sweroside-2'-(3'',5'',3'''-trihydroxydiphenyl)-2''-carboxylic acid ester (English)

5 October 2016

Swertia chirata

4 references

Unexpected Biosynthetic Precursors of Amarogentin − A Retrobiosynthetic13C NMR Study

Amarogentin, a naturally occurring secoiridoid glycoside and a newly recognized inhibitor of topoisomerase I from Leishmania donovani.

Regulation of hazardous exposure by protective exposure: modulation of phase II detoxification and lipid peroxidation by Camellia sinensis and Swertia chirata

Zwei stark bittere glucoside aus swertia japonica makino: Amarogentin und amaroswerin

Great yellow gentian

4 references

The chemical constituents of fresh Gentian Root

Inhibition of vascular smooth muscle cell proliferation by Gentiana lutea root extracts

Va-Mycorrhiza in Gentiana lutea, the Importance of Cultivation and Influence on Constituents

SUGARS, BITTER SUBSTANCES AND ESSENTIAL OILS OF GENTIANA LUTEA L. IN DEPENDENCE OF ECOTYPE, PLANT AGE AND STAGE OF DEVELOPMENT

Gentiana purpurea

1 reference

Preparative On-Line Overpressure Layer Chromatography (OPLC): a New Separation Technique for Natural Products

Gentianella nitida

2 references

A new secoiridoid glucoside, amaronitidin, from the Peruvian folk medicine "Hercampuri" (Gentianella nitida).

Secoiridoids and xanthones from Gentianella nitida

Swertia japonica

6 references

Amarogentin, amaroswerin and four xanthones from hairy root cultures of Swertia japonica

Studies on Monoterpene Glucosides and Related Compounds. LXV. Biosynthesis of the Biphenylcarboxylic Acid Moiety of Amarogentin and Amaroswerin

Studies on the mutagenicity of Swertiae Herba. I. Identification of the mutagenic components.

Studies on the mutagenicity of swertiae herba. III. Components which become mutagenic on nitrite treatment

Two bitter biphenyl glucosides from Swertia japonica

Quantitative Determination of Bitter Components in Swertiae Herba

Swertia leducii

1 reference

Secoiridoid glucosides from Swertia mileensis

Swertia mileensis

1 reference

Secoiridoid glucosides from Swertia mileensis

physically interacts with

taste receptor type 2

subject has role

1 reference

The Molecular Receptive Ranges of Human TAS2R Bitter Taste Receptors

has characteristic

1 reference

Commons category

Amarogentin

0 references

Identifiers

InChI=1S/C29H30O13/c1-2-16-17-6-7-38-26(36)19(17)12-39-28(16)42-29-25(24(35)23(34)21(11-30)40-29)41-27(37)22-18(9-15(32)10-20(22)33)13-4-3-5-14(31)8-13/h2-5,8-10,12,16-17,21,23-25,28-35H,1,6-7,11H2/t16-,17+,21-,23-,24+,25-,28+,29+/m1/s1

1 reference

language of work or name

sweroside-2'-(3'',5'',3'''-trihydroxydiphenyl)-2''-carboxylic acid ester (English)

5 October 2016

DBOVHQOUSDWAPQ-WTONXPSSSA-N

2 references

language of work or name

sweroside-2'-(3'',5'',3'''-trihydroxydiphenyl)-2''-carboxylic acid ester (English)

5 October 2016

ChEBI release 2020-09-01

CAS Registry Number

2 references

language of work or name

amarogentin (English)

5 October 2016

DBOVHQOUSDWAPQ-WTONXPSSSA-N

CAS Common Chemistry

10 April 2021

https://commonchemistry.cas.org/detail?cas_rn=21018-84-8

1 reference

language of work or name

Amarogentin (English)

5 October 2016

2 references

language of work or name

sweroside-2'-(3'',5'',3'''-trihydroxydiphenyl)-2''-carboxylic acid ester (English)

5 October 2016

matched by identifier from

DBOVHQOUSDWAPQ-WTONXPSSSA-N

Reaxys registry number

74677

1 reference

language of work or name

amarogentin (English)

5 October 2016

mapping relation type

2 references

language of work or name

amarogentin (English)

5 October 2016

matched by identifier from

International Chemical Identifier

InChI=1S/C29H30O13/c1-2-16-17-6-7-38-26(36)19(17)12-39-28(16)42-29-25(24(35)23(34)21(11-30)40-29)41-27(37)22-18(9-15(32)10-20(22)33)13-4-3-5-14(31)8-13/h2-5,8-10,12,16-17,21,23-25,28-35H,1,6-7,11H2/t16-,17+,21-,23-,24+,25-,28+,29+/m1/s1

1 reference

imported from Wikimedia project

English Wikipedia

2 references

based on heuristic

inferred from InChIKey

matched by identifier from

DBOVHQOUSDWAPQ-WTONXPSSSA-N

UniChem compound ID

1 reference

splash10-004i-0090000000-e367040246ae42730994

0 references

639-021-0

1 reference

ECHA Substance Infocard ID

ECHA Substance Infocard ID

1 reference

ECHA Substance Infocard ID

1 reference

language of work or name

amarogentin (English)

5 October 2016

2 references

Global Substance Registration System

language of work or name

AMAROGENTIN (English)

5 October 2016

matched by identifier from

DBOVHQOUSDWAPQ-WTONXPSSSA-N

Probes And Drugs ID

0 references

1 reference

language of work or name

amarogentin (English)

5 October 2016

1 reference

Freebase Data Dumps

publication date

28 October 2013

Microsoft Academic ID

0 references

Sitelinks

Wikipedia(9 entries)

Wikibooks(0 entries)

Wikinews(0 entries)

Wikiquote(0 entries)

Wikisource(0 entries)

Wikiversity(0 entries)

Wikivoyage(0 entries)

Wiktionary(0 entries)

Multilingual sites(1 entry)

commonswiki Category:Amarogentin

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