Page last updated: 2024-11-06

loganic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

loganic acid: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

loganic acid : A cyclopentapyran that is 1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid substituted at positions 1, 6 and 7 by beta-D-glucosyloxy, hydroxy and methyl groups respectively [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID89640
CHEMBL ID1081585
CHEBI ID30632
SCHEMBL ID308008
MeSH IDM0043795

Synonyms (55)

Synonym
(1s,4as,6s,7r,7as)-1-(beta-d-glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
CHEBI:30632 ,
DIVK1C_006639
KBIO1_001583
SDCCGMLS-0066805.P001
SPECTRUM_001509
SPECTRUM4_001690
BSPBIO_003530
SPECTRUM5_000340
C01512
loganic acid
22255-40-9
KBIOSS_001989
KBIOGR_001960
KBIO3_002760
KBIO2_001989
KBIO2_004557
KBIO2_007125
SPECPLUS_000543
SPECTRUM2_001971
SPBIO_002121
SPECTRUM3_001930
SPECTRUM1504071
NCGC00178007-01
(1s,4as,6s,7r,7as)-6-hydroxy-7-methyl-1-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
CHEMBL1081585
(1s,4as,6s,7r,7as)-6-hydroxy-7-methyl-1-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
(1s-(1alpha,4aalpha,6alpha,7alpha,7aalpha))-1-(beta-d-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta(c)pyran-4-carboxylic acid
ux3j3kk2ug ,
einecs 244-875-9
unii-ux3j3kk2ug
CCG-39437
SCHEMBL308008
W-107488
loganic-acid
mfcd00017417
norloganin
loganic acid, >=95% (lc/ms-elsd)
NCGC00178007-02
(1s,4as,6s,7r,7as)-1-(beta-d-glucopyranosyloxy)-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxyl
AKOS032962058
HY-N0513
(1s,4as,6s,7r,7as)-6-hydroxy-7-methyl-1-((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
DTXSID80944913
eqv ,
Q19597767
CS-0009052
A878637
[1s-(1a,4aa,6a,7a,7aa)]-1-(beta-d-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylic acid
MS-26101
S9191
cyclopenta(c)pyran-4-carboxylic acid, 1-(.beta.-d-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methyl-, (1s-(1.alpha.,4a.alpha.,6.alpha.,7.alpha.,7a.alpha.))-
(1s,4as,6s,7r,7as)-1-(.beta.-d-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-6-hydroxy-7-methylcyclopenta(c)pyran-4-carboxylic acid
cyclopenta(c)pyran-4-carboxylic acid, 1.alpha.-(.beta.-d-glucopyranosyloxy)-1,4a.alpha.,5,6,7,7a.alpha.-hexahydro-6.alpha.-hydroxy-7.alpha.-methyl-
loganin acid

Research Excerpts

Overview

Loganic acid (LA) is an iridoid glycoside reported to have antioxidant and anti-inflammatory properties.

ExcerptReferenceRelevance
"Loganic acid (LA) is an iridoid glycoside reported to have antioxidant and anti-inflammatory properties."( Loganic acid protects against ulcerative colitis by inhibiting TLR4/NF-κB mediated inflammation and activating the SIRT1/Nrf2 anti-oxidant responses in-vitro and in-vivo.
Jain, S; Naidu, VGM; Panda, SR; Prakash, AN; Prasad, N; Puppala, ER; Ravichandiran, V; Singh, M, 2023
)
3.07

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
glucoside
cyclopentapyran
alpha,beta-unsaturated monocarboxylic acidA monocarboxylic acid in which the carbon of the carboxy group is directly attached to a C=C or C#C bond.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (20)

Assay IDTitleYearJournalArticle
AID977602Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID1251036Inhibition of COX1 (unknown origin) assessed as PGH2 production at 10 uM by measuring PGH2alpha level by enzyme immunoassay2015Bioorganic & medicinal chemistry letters, Oct-15, Volume: 25, Issue:20
In vitro COX-1 and COX-2 enzyme inhibitory activities of iridoids from Penstemon barbatus, Castilleja tenuiflora, Cresentia alata and Vitex mollis.
AID1251039Inhibition of COX2 (unknown origin) assessed as PGH2 production at 10 uM by measuring PGH2alpha level by enzyme immunoassay2015Bioorganic & medicinal chemistry letters, Oct-15, Volume: 25, Issue:20
In vitro COX-1 and COX-2 enzyme inhibitory activities of iridoids from Penstemon barbatus, Castilleja tenuiflora, Cresentia alata and Vitex mollis.
AID977599Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID467895Antiviral activity against HCV expressing E1E2 glycoprotein with Vpr-deficient HIV vector assessed as inhibition of viral entry in human Huh7 cells at 20 ug/ml after 72 hrs by luciferase reporter gene assay in presence of beta-glucosidase enzyme for 0.5 h2009Journal of natural products, Dec, Volume: 72, Issue:12
Lamiridosins, hepatitis C virus entry inhibitors from Lamium album.
AID1251038Inhibition of COX1 (unknown origin) assessed as PGH2 production at 100 uM by measuring PGH2alpha level by enzyme immunoassay2015Bioorganic & medicinal chemistry letters, Oct-15, Volume: 25, Issue:20
In vitro COX-1 and COX-2 enzyme inhibitory activities of iridoids from Penstemon barbatus, Castilleja tenuiflora, Cresentia alata and Vitex mollis.
AID467894Antiviral activity against HCV expressing E1E2 glycoprotein with Vpr-deficient HIV vector assessed as inhibition of viral entry in human Huh7 cells at 20 ug/ml measured after 72 hrs by luciferase reporter gene assay2009Journal of natural products, Dec, Volume: 72, Issue:12
Lamiridosins, hepatitis C virus entry inhibitors from Lamium album.
AID1251040Inhibition of COX2 (unknown origin) assessed as PGH2 production at 35 uM by measuring PGH2alpha level by enzyme immunoassay2015Bioorganic & medicinal chemistry letters, Oct-15, Volume: 25, Issue:20
In vitro COX-1 and COX-2 enzyme inhibitory activities of iridoids from Penstemon barbatus, Castilleja tenuiflora, Cresentia alata and Vitex mollis.
AID1251037Inhibition of COX1 (unknown origin) assessed as PGH2 production at 35 uM by measuring PGH2alpha level by enzyme immunoassay2015Bioorganic & medicinal chemistry letters, Oct-15, Volume: 25, Issue:20
In vitro COX-1 and COX-2 enzyme inhibitory activities of iridoids from Penstemon barbatus, Castilleja tenuiflora, Cresentia alata and Vitex mollis.
AID1251041Inhibition of COX2 (unknown origin) assessed as PGH2 production at 100 uM by measuring PGH2alpha level by enzyme immunoassay2015Bioorganic & medicinal chemistry letters, Oct-15, Volume: 25, Issue:20
In vitro COX-1 and COX-2 enzyme inhibitory activities of iridoids from Penstemon barbatus, Castilleja tenuiflora, Cresentia alata and Vitex mollis.
AID467896Antiviral activity against HCV expressing E1E2 glycoprotein with Vpr-deficient HIV vector assessed as inhibition of viral entry in human Huh7 cells at 20 ug/ml after 72 hrs by luciferase reporter gene assay in presence of beta-glucosidase enzyme for 4 hrs2009Journal of natural products, Dec, Volume: 72, Issue:12
Lamiridosins, hepatitis C virus entry inhibitors from Lamium album.
AID467898Inhibition of human recombinant GST-tagged CD81 protein assessed as HCV E1E2 binding after 1 hr by Western blot analysis2009Journal of natural products, Dec, Volume: 72, Issue:12
Lamiridosins, hepatitis C virus entry inhibitors from Lamium album.
AID467897Antiviral activity against HCV infected in human Huh7 cells assessed as inhibition of viral replication after 72 hrs by NS5A staining2009Journal of natural products, Dec, Volume: 72, Issue:12
Lamiridosins, hepatitis C virus entry inhibitors from Lamium album.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1159550Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening2015Nature cell biology, Nov, Volume: 17, Issue:11
6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (59)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (3.39)18.7374
1990's1 (1.69)18.2507
2000's10 (16.95)29.6817
2010's29 (49.15)24.3611
2020's17 (28.81)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 27.35

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index27.35 (24.57)
Research Supply Index4.09 (2.92)
Research Growth Index5.66 (4.65)
Search Engine Demand Index31.58 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (27.35)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (1.69%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other58 (98.31%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]