ASPERULOSIDIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H24O12
Molecular Weight	432.376
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=DGDWCRWJRNMRKX-DILZHRMZSA-N

InChI=1S/C18H24O12/c1-6(20)27-4-7-2-9(21)12-8(16(25)26)5-28-17(11(7)12)30-18-15(24)14(23)13(22)10(3-19)29-18/h2,5,9-15,17-19,21-24H,3-4H2,1H3,(H,25,26)/t9-,10+,11+,12-,13+,14-,15+,17-,18-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C18H24O12
Molecular Weight	432.376
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
NF-kappa B signaling pathway 84 Target ID: map04064 Sources: https://www.ncbi.nlm.nih.gov/pubmed/30668407 \| https://www.ncbi.nlm.nih.gov/pubmed/30002289	Inhibitor 8297
TGF-beta signaling pathway 8 Target ID: map04350 Sources: https://www.ncbi.nlm.nih.gov/pubmed/30668407	Inhibitor 8297

PubMed

Title	Date	PubMed
Increased plasma 3,5,3'-triiodothyronine sulfate in rats with inhibited type I iodothyronine deiodinase activity, as measured by radioimmunoassay.	1989 Feb	2912698
An LC-MS method for simultaneous determination of five iridoids from Zhi-zi-chi Decoction in rat brain microdialysates and tissue homogenates: towards an in depth study for its antidepressive activity.	2014 Aug 15	25049209
[Study on chemical constituents of iridoids from eucommiae folium].	2014 Feb	25095345
Isolation and purification of six iridoid glycosides from gardenia jasminoides fruit by medium-pressure liquid chromatography combined with macroporous resin chromatography.	2015 Dec	26768549
Analysis of Organic Acids, Deacetyl Asperulosidic Acid and Polyphenolic Compounds as a Potential Tool for Characterization of Noni (Morinda citrifolia) Products.	2015 Nov	26749805
Acousto-optic tunable filter near-infrared spectroscopy for in-line monitoring liquid-liquid extraction of Gardenia jasminoides Ellis based on statistical analysis.	2015 Oct	26601419
[Identification of Oldenlandia diffusa by UPLC Fingerprint Coupled with Chemometrics Methods].	2016 Apr	30132312
Morinda citrifolia Linn. Reduces Parasite Load and Modulates Cytokines and Extracellular Matrix Proteins in C57BL/6 Mice Infected with Leishmania (Leishmania) amazonensis.	2016 Aug	27579922
α-Glucosidase and α-Amylase Inhibitors from Arcytophyllum thymifolium.	2016 Aug 26	27509358
LC/MS/MS determination and pharmacokinetic study of iridoid glycosides monotropein and deacetylasperulosidic acid isomers in rat plasma after oral administration of Morinda officinalis extract.	2016 Feb	26053360
Phytochemistry, micromorphology and bioactivities of Ajuga chamaepitys (L.) Schreb. (Lamiaceae, Ajugoideae): Two new harpagide derivatives and an unusual iridoid glycosides pattern.	2016 Sep	27373875
Anti-malarial synergy of secondary metabolites from Morinda lucida Benth.	2017 Mar 6	28153468
Mid-infrared and near-infrared spectroscopy for rapid detection of Gardeniae Fructus by a liquid-liquid extraction process.	2017 Oct 25	28645015
Iridoids and sfingolipids from Hedyotis diffusa.	2018 Jan	29122633
Asperuloside and Asperulosidic Acid Exert an Anti-Inflammatory Effect via Suppression of the NF-κB and MAPK Signaling Pathways in LPS-Induced RAW 264.7 Macrophages.	2018 Jul 12	30002289
Simultaneous Analysis of Iridoid Glycosides and Anthraquinones in Morinda officinalis Using UPLC-QqQ-MS/MS and UPLC-Q/TOF-MS(E).	2018 May 3	29751518
Pharmacokinetics and tissue distribution of monotropein and deacetyl asperulosidic acid after oral administration of extracts from Morinda officinalis root in rats.	2018 Oct 24	30355303
In silico screening of anthraquinones from Prismatomeris memecyloides as novel phosphodiesterase type-5 inhibitors (PDE-5Is).	2018 Oct-Dec	30286869
Anti-renal fibrosis effect of asperulosidic acid via TGF-β1/smad2/smad3 and NF-κB signaling pathways in a rat model of unilateral ureteral obstruction.	2019 Feb	30668407
Anti-inflammatory constituents from Psychotria prainii H. Lév.	2019 Mar	29212359

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:01:34 GMT 2023` Edited by `admin` on `Sat Dec 16 10:01:34 GMT 2023`
Record UNII	39LA4NOT5K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ASPERULOSIDIC ACID

Common Name

English

CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 7-((ACETYLOXY)METHYL)-1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,7A-TETRAHYDRO-5-HYDROXY-, (1S-(1.ALPHA.,4A.ALPHA.,5.BETA.,7A.ALPHA.))-

Systematic Name

English

CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1.ALPHA.-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A.ALPHA.,5,7A.ALPHA.-TETRAHYDRO-5.BETA.-HYDROXY-7-(HYDROXYMETHYL)-, 7-ACETATE

Systematic Name

English

CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 7-((ACETYLOXY)METHYL)-1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,7A-TETRAHYDRO-5-HYDROXY-, (1S,4AS,5S,7AS)-

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID201315882

Created by admin on Sat Dec 16 10:01:34 GMT 2023 , Edited by admin on Sat Dec 16 10:01:34 GMT 2023

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FDA UNII

39LA4NOT5K

Created by admin on Sat Dec 16 10:01:34 GMT 2023 , Edited by admin on Sat Dec 16 10:01:34 GMT 2023

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PUBCHEM

11968867

Created by admin on Sat Dec 16 10:01:34 GMT 2023 , Edited by admin on Sat Dec 16 10:01:34 GMT 2023

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CAS

25368-11-0

Created by admin on Sat Dec 16 10:01:34 GMT 2023 , Edited by admin on Sat Dec 16 10:01:34 GMT 2023

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