Compounds > secoxyloganin
Page last updated: 2024-12-08

secoxyloganin

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

Description

secoxyloganin: from Guettarda playpoda [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

secoxyloganin : A secoiridoid glycoside that is [(2R,3R,4S)-2-hydroxy-5-(methoxycarbonyl)-3-vinyl-3,4-dihydro-2H-pyran-4-yl]acetic acid in which the anometric hydroxy group has been converted to the corresponding beta-D-glucoside. It has been isolated from several plant species and exhibits antioxidant and anti-allergic properties. [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]

FloraRankFlora DefinitionFamilyFamily Definition
Guettardagenus[no description available]RubiaceaeThe Madder plant family of the order Gentianales (formerly Rubiales), subclass Asteridae, class Magnoliopsida includes important medicinal plants that provide QUININE; IPECAC; and COFFEE. They have opposite leaves and interpetiolar stipules.[MeSH]

Cross-References

ID SourceID
PubMed CID162868
CHEBI ID132712
MeSH IDM0165533

Synonyms (29)

Synonym
secoxyloganin
MEGXP0_000724
(2s,3r,4s)-3-ethenyl-2-(beta-d-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2h-pyran-4-acetic acid
[(2s,3r,4s)-3-ethenyl-2-(beta-d-glucopyranosyloxy)-5-(methoxycarbonyl)-3,4-dihydro-2h-pyran-4-yl]acetic acid
58822-47-2
CHEBI:132712 ,
secoxy-loganin
2-[(2s,3r,4s)-3-ethenyl-5-methoxycarbonyl-2-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2h-pyran-4-yl]acetic acid
2h-pyran-4-acetic acid, 3-ethenyl-2-(beta-d-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-, (2s-(2alpha,3beta,4beta))-
(2s-(2alpha,3beta,4beta))-3-ethenyl-2-(beta-d-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2h-pyran-4-acetic acid
unii-65j8k23l9l
65j8k23l9l ,
S9435
AC-34945
mfcd20260822
NCGC00380454-01
ncgc00380454-01_c17h24o11_2h-pyran-4-acetic acid, 3-ethenyl-2-(beta-d-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-, (2s,3r,4s)-
AKOS032948707
HY-N3009
2-((2s,3r,4s)-5-(methoxycarbonyl)-2-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)-3-vinyl-3,4-dihydro-2h-pyran-4-yl)acetic acid
[3-ethenyl-2-(hexopyranosyloxy)-5-(methoxycarbonyl)-3,4-dihydro-2h-pyran-4-yl]acetic acid
DTXSID90974342
CCG-268689
CS-0022922
(2s,3r,4s)-3-ethenyl-2-(.beta.-d-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2h-pyran-4-acetic acid
secologanoside 11-methyl ester
2h-pyran-4-acetic acid, 3-ethenyl-2-(.beta.-d-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-, (2s,3r,4s)-
AS-78339
2h-pyran-4-acetic acid, 3-ethenyl-2-(beta-d-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-, (2s,3r,4s)-

Research Excerpts

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 (3)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
antioxidantA substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
anti-allergic agentA drug used to treat allergic reactions.
[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 (7)

ClassDescription
methyl esterAny carboxylic ester resulting from the formal condensation of a carboxy group with methanol.
pyrans
enoate esterAn alpha,beta-unsaturated carboxylic ester of general formula R(1)R(2)C=CR(3)-C(=O)OR(4) (R(4) =/= H) in which the ester C=O function is conjugated to a C=C double bond at the alpha,beta position.
beta-D-glucosideAny D-glucoside in which the anomeric centre has beta-configuration.
monosaccharide derivativeA carbohydrate derivative that is formally obtained from a monosaccharide.
dicarboxylic acid monoesterA monoester of a dicarboxylic acid.
secoiridoid glycosideA glycoside of any secoiridoid.
[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 (5)

Assay IDTitleYearJournalArticle
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.
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.
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (7.14)18.7374
1990's0 (0.00)18.2507
2000's2 (14.29)29.6817
2010's8 (57.14)24.3611
2020's3 (21.43)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 27.11

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 Index27.11 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index5.14 (4.65)
Search Engine Demand Index29.35 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (27.11)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
inositol
Inositol: An isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1379) Inositol phospholipids are important in signal transduction.. inositol : Any cyclohexane-1,2,3,4,5,6-hexol.. 1D-chiro-inositol : Belonging to the inositol family of compounds, D-chiro-inositol (DCI) is an isomer of glucose. It is an important secondary messenger in insulin signal transduction.. muco-inositol : An inositol that is cyclohexane-1,2,3,4,5,6-hexol having a (1R,2R,3r,4R,5S,6r)-configuration.		2.110cyclitol;
hexol
sucrose
Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.		2.110glycosyl glycosidealgal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
osmolyte;
Saccharomyces cerevisiae metabolite;
sweetening agent
quinic acid
(-)-quinic acid : The (-)-enantiomer of quinic acid.		2.1310
camptothecin
NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source		2.4110delta-lactone;
pyranoindolizinoquinoline;
quinoline alkaloid;
tertiary alcohol		antineoplastic agent;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
genotoxin;
plant metabolite
glucose, (beta-d)-isomer
beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.		3.1250D-glucopyranoseepitope;
mouse metabolite
betulinic acid
[no description available]		2.1310hydroxy monocarboxylic acid;
pentacyclic triterpenoid		anti-HIV agent;
anti-inflammatory agent;
antimalarial;
antineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
plant metabolite
loganin
[no description available]		3.4270beta-D-glucoside;
cyclopentapyran;
enoate ester;
iridoid monoterpenoid;
methyl ester;
monosaccharide derivative;
secondary alcohol		anti-inflammatory agent;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
EC 3.4.23.46 (memapsin 2) inhibitor;
neuroprotective agent;
plant metabolite
loganic acid
loganic acid: structure. 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		1.9710alpha,beta-unsaturated monocarboxylic acid;
cyclopentapyran;
glucoside		plant metabolite
phytol
[no description available]		2.1310
sweroside
[no description available]		2.9940glycoside
secologanin
(-)-secologanin : An iridoid monoterpenoid that is acetaldehyde in which on of the hydrogens of the methyl group has been replaced by a 2-(beta-D-glucopyranosyloxy)-3,4-dihydro-2H-pyran-4-yl group which is substituted at positions 3 and 5 by a vinyl and a methoxycarbonyl group, respectively (the 2S,3R,4S stereoisomer).		7.5220aldehyde;
beta-D-glucoside;
enoate ester;
methyl ester;
pyrans;
secoiridoid glycoside		plant metabolite
lupeol
[no description available]		2.1310pentacyclic triterpenoid;
secondary alcohol		anti-inflammatory drug;
plant metabolite
iridoids
Iridoids: A type of MONOTERPENES, derived from geraniol. They have the general form of cyclopentanopyran, but in some cases, one of the rings is broken as in the case of secoiridoid. They are different from the similarly named iridals (TRITERPENES).		3.4270
glycosides
[no description available]		2.3920
caffeic acid
trans-caffeic acid : The trans-isomer of caffeic acid.		2.4620caffeic acidgeroprotector;
mouse metabolite
chlorogenic acid
caffeoylquinic acid: Antiviral Agent; structure in first source. chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3.		3.1750cinnamate ester;
tannin		food component;
plant metabolite
luteolin
[no description available]		2.03103'-hydroxyflavonoid;
tetrahydroxyflavone		angiogenesis inhibitor;
anti-inflammatory agent;
antineoplastic agent;
apoptosis inducer;
c-Jun N-terminal kinase inhibitor;
EC 2.3.1.85 (fatty acid synthase) inhibitor;
immunomodulator;
nephroprotective agent;
plant metabolite;
radical scavenger;
vascular endothelial growth factor receptor antagonist
luteolin-7-glucoside
luteolin-7-glucoside: has both antiasthmatic and antineoplastic activities; has 3C protease inhibitory activity; isolated from Ligustrum lucidum. luteolin 7-O-beta-D-glucoside : A glycosyloxyflavone that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.		2.0310beta-D-glucoside;
glycosyloxyflavone;
monosaccharide derivative;
trihydroxyflavone		antioxidant;
plant metabolite
chrysoeriol
chrysoeriol: isolated from leaves of Eurya japonica & E. emarginata. 4',5,7-trihydroxy-3'-methoxyflavone : The 3'-O-methyl derivative of luteolin.		2.110monomethoxyflavone;
trihydroxyflavone		antineoplastic agent;
antioxidant;
metabolite
rutin
Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.		2.4620disaccharide derivative;
quercetin O-glucoside;
rutinoside;
tetrahydroxyflavone		antioxidant;
metabolite
methyl chlorogenate
methyl chlorogenate: from Eriobotrya japonica; structure in first source		2.1310quinic acid
muramidase
Muramidase: A basic enzyme that is present in saliva, tears, egg white, and many animal fluids. It functions as an antibacterial agent. The enzyme catalyzes the hydrolysis of 1,4-beta-linkages between N-acetylmuramic acid and N-acetyl-D-glucosamine residues in peptidoglycan and between N-acetyl-D-glucosamine residues in chitodextrin. EC 3.2.1.17.		2.0610
ConditionIndicatedRelationship StrengthStudiesTrials
Congenital Zika Syndrome
[description not available]		02.2510
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.2510
Zika Virus Infection
A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.		02.2510
Anasarca
[description not available]		02.1310
Edema
Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.		02.1310
Allergic Reaction
[description not available]		02.0610
Hypersensitivity
Altered reactivity to an antigen, which can result in pathologic reactions upon subsequent exposure to that particular antigen.		02.0610
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.0310