Page last updated: 2024-12-10

apiin

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

Description

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

apiin : A beta-D-glucoside having a beta-D-apiosyl residue at the 2-position and a 5,4'-dihydroxyflavon-7-yl moiety at the anomeric position. [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 CID5280746
CHEMBL ID1535342
CHEBI ID15932
SCHEMBL ID316910
MeSH IDM0059076

Synonyms (67)

Synonym
BRD-K52379519-001-02-0
5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4h-chromen-7-yl 2-o-[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]-beta-d-glucopyranoside
7-((2-o-beta-d-apiofuranosyl-beta-d-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4h-1-benzopyranone
CHEBI:15932 ,
5,7,4'-trihydroxyflavone 7-o-[beta-d-apiosyl-(1->2)-beta-d-glucoside]
5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4h-chromen-7-yl 3-c-(hydroxymethyl)-beta-d-glycero-tetrofuranosyl-(1->2)-beta-d-glucopyranoside
DIVK1C_007035
SDCCGMLS-0066949.P001
MLS000575008
smr000156232
SPECTRUM4_001817
SPECTRUM_000204
BSPBIO_003313
SPECTRUM5_000553
C04858
apioside
7-[(2-o-d-apio-beta-d-furanosyl-beta-d-glucopyranosyl)oxy]-5-hydroxy-2-(4-hydroxy-phenyl)-4h-1-benzopyran-4-one
26544-34-3
apiin
7-o-(beta-d-apiofuranosyl-1,2-beta-d-glucosyl)-5,7,4'-trihydroxyflavone
apigenin 7-o-[beta-d-apiosyl-(1->2)-beta-d-glucoside]
KBIO2_003252
KBIO3_002815
KBIO1_001979
KBIO2_005820
KBIO2_000684
KBIOSS_000684
KBIOGR_002458
SPECPLUS_000939
SPECTRUM2_001800
SPECTRUM3_001787
SPBIO_001759
SPECTRUM350025
NCGC00178147-01
7-o-(beta-d-apiofuranosyl-(1-2)-beta-d-glucosyl)-apigenin
7-o-(beta-d-apiofuranosyl-(1-2)-beta-d-glucosyl)-5,7,4'-trihydroxyflavone
7-[(2s,3r,4s,5s,6r)-3-[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one
HMS2209P05
apigenin-7-apioglucoside
7-((2-o-d-apio-beta-d-furanosyl-beta-d-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4h-1-benzopyran-4-one
unii-6qu3eze37u
einecs 247-780-0
6qu3eze37u ,
CCG-39950
apiin [mi]
7-((2-o-d-apio-.beta.-d-furanosyl-.beta.-d-glucopyranosyl)oxy)- 5-hydroxy-2-(4-hydroxyphenyl)-4h-1-benzopyran-4-one
7-((2-o-.beta.-d-apiofuranosyl-.beta.-d-glucopyranosyl)oxy)-5- hydroxy-2-(4-hydroxyphenyl)-4h-1-benzopyranone
CHEMBL1535342
bdbm153268
apiin (11)
SCHEMBL316910
sr-01000712126
SR-01000712126-2
NTDLXWMIWOECHG-YRCFQSNFSA-N
7-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-4h-chromen-4-one
AS-74876
AKOS030632988
Q2858300
7-(((2s,3r,4s,5s,6r)-3-(((2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4h-chromen-4-one
4h-1-benzopyran-4-one, 7-[(2-o-d-apio-beta-d-furanosyl-beta-d-glucopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-
HY-N0577
CS-0009113
DTXSID90949393
7-((2-o-d-apio-beta-d-furanosyl-beta-d-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxy-phenyl)-4h-1-benzopyran-4-one
apigenin 7-o-(beta-d-apiosyl-(1->2)-beta-d-glucoside)
5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4h-chromen-7-yl 2-o-((2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl)-beta-d-glucopyranoside
5,7,4'-trihydroxyflavone 7-o-(beta-d-apiosyl-(1->2)-beta-d-glucoside)

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" The flavone could be detected in red blood cells without showing dose-response characteristics."( Bioavailability of apigenin from apiin-rich parsley in humans.
Bolarinwa, A; Linseisen, J; Meyer, H; Wolfram, G, 2006
)
0.62
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
EC 3.2.1.18 (exo-alpha-sialidase) inhibitorAn antiviral drug targeted at influenza viruses. Its mode of action consists of blocking the function of the viral neuraminidase protein (EC 3.2.1.18), thus preventing the virus from budding from the host cell.
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
beta-D-glucosideAny D-glucoside in which the anomeric centre has beta-configuration.
dihydroxyflavoneAny hydroxyflavone in which two ring hydrogens are replaced by hydroxy substituents.
glycosyloxyflavoneA member of the class of flavones having one or more glycosyl residues attached at unspecified positions.
[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]

Protein Targets (7)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Beta-lactamaseEscherichia coli K-12Potency0.50120.044717.8581100.0000AID485294
bromodomain adjacent to zinc finger domain 2BHomo sapiens (human)Potency0.70790.707936.904389.1251AID504333
gemininHomo sapiens (human)Potency0.14580.004611.374133.4983AID624297
muscleblind-like protein 1 isoform 1Homo sapiens (human)Potency22.38720.00419.962528.1838AID2675
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Aurora kinase BHomo sapiens (human)IC50 (µMol)12.14000.00030.96349.8000AID1801097
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (68)

Processvia Protein(s)Taxonomy
B cell apoptotic processProgrammed cell death protein 1Homo sapiens (human)
adaptive immune responseProgrammed cell death protein 1Homo sapiens (human)
negative regulation of tolerance inductionProgrammed cell death protein 1Homo sapiens (human)
negative regulation of T cell mediated immune response to tumor cellProgrammed cell death protein 1Homo sapiens (human)
negative regulation of B cell apoptotic processProgrammed cell death protein 1Homo sapiens (human)
apoptotic processProgrammed cell death protein 1Homo sapiens (human)
humoral immune responseProgrammed cell death protein 1Homo sapiens (human)
negative regulation of immune responseProgrammed cell death protein 1Homo sapiens (human)
negative regulation of T cell activationProgrammed cell death protein 1Homo sapiens (human)
regulatory T cell apoptotic processProgrammed cell death protein 1Homo sapiens (human)
regulation of immune responseProgrammed cell death protein 1Homo sapiens (human)
positive regulation of T cell apoptotic processProgrammed cell death protein 1Homo sapiens (human)
negative regulation of transcription by RNA polymerase IIAurora kinase BHomo sapiens (human)
mitotic cell cycleAurora kinase BHomo sapiens (human)
mitotic cytokinesisAurora kinase BHomo sapiens (human)
negative regulation of B cell apoptotic processAurora kinase BHomo sapiens (human)
protein phosphorylationAurora kinase BHomo sapiens (human)
spindle organizationAurora kinase BHomo sapiens (human)
attachment of spindle microtubules to kinetochoreAurora kinase BHomo sapiens (human)
abscissionAurora kinase BHomo sapiens (human)
negative regulation of protein bindingAurora kinase BHomo sapiens (human)
positive regulation of telomere maintenance via telomeraseAurora kinase BHomo sapiens (human)
negative regulation of cytokinesisAurora kinase BHomo sapiens (human)
positive regulation of cytokinesisAurora kinase BHomo sapiens (human)
protein localization to kinetochoreAurora kinase BHomo sapiens (human)
cellular response to UVAurora kinase BHomo sapiens (human)
cleavage furrow formationAurora kinase BHomo sapiens (human)
post-translational protein modificationAurora kinase BHomo sapiens (human)
cell cycle G2/M phase transitionAurora kinase BHomo sapiens (human)
mitotic cytokinesis checkpoint signalingAurora kinase BHomo sapiens (human)
negative regulation of innate immune responseAurora kinase BHomo sapiens (human)
protein autophosphorylationAurora kinase BHomo sapiens (human)
mitotic spindle midzone assemblyAurora kinase BHomo sapiens (human)
positive regulation of telomerase activityAurora kinase BHomo sapiens (human)
regulation of chromosome segregationAurora kinase BHomo sapiens (human)
positive regulation of mitotic sister chromatid segregationAurora kinase BHomo sapiens (human)
positive regulation of mitotic cell cycle spindle assembly checkpointAurora kinase BHomo sapiens (human)
mitotic spindle assemblyAurora kinase BHomo sapiens (human)
negative regulation of cGAS/STING signaling pathwayAurora kinase BHomo sapiens (human)
regulation of signal transduction by p53 class mediatorAurora kinase BHomo sapiens (human)
positive regulation of mitotic sister chromatid separationAurora kinase BHomo sapiens (human)
positive regulation of attachment of mitotic spindle microtubules to kinetochoreAurora kinase BHomo sapiens (human)
positive regulation of mitotic cytokinesisAurora kinase BHomo sapiens (human)
positive regulation of telomere cappingAurora kinase BHomo sapiens (human)
positive regulation of lateral attachment of mitotic spindle microtubules to kinetochoreAurora kinase BHomo sapiens (human)
mitotic spindle organizationAurora kinase BHomo sapiens (human)
regulation of cytokinesisAurora kinase BHomo sapiens (human)
regulation of activated T cell proliferationProgrammed cell death 1 ligand 1Homo sapiens (human)
regulation of T cell apoptotic processProgrammed cell death 1 ligand 1Homo sapiens (human)
regulation of activated CD4-positive, alpha-beta T cell apoptotic processProgrammed cell death 1 ligand 1Homo sapiens (human)
adaptive immune responseProgrammed cell death 1 ligand 1Homo sapiens (human)
negative regulation of T cell mediated immune response to tumor cellProgrammed cell death 1 ligand 1Homo sapiens (human)
immune responseProgrammed cell death 1 ligand 1Homo sapiens (human)
signal transductionProgrammed cell death 1 ligand 1Homo sapiens (human)
cell surface receptor signaling pathwayProgrammed cell death 1 ligand 1Homo sapiens (human)
positive regulation of cell migrationProgrammed cell death 1 ligand 1Homo sapiens (human)
T cell costimulationProgrammed cell death 1 ligand 1Homo sapiens (human)
negative regulation of type II interferon productionProgrammed cell death 1 ligand 1Homo sapiens (human)
negative regulation of interleukin-10 productionProgrammed cell death 1 ligand 1Homo sapiens (human)
positive regulation of interleukin-10 productionProgrammed cell death 1 ligand 1Homo sapiens (human)
response to cytokineProgrammed cell death 1 ligand 1Homo sapiens (human)
TRIF-dependent toll-like receptor signaling pathwayProgrammed cell death 1 ligand 1Homo sapiens (human)
positive regulation of T cell proliferationProgrammed cell death 1 ligand 1Homo sapiens (human)
positive regulation of DNA-templated transcriptionProgrammed cell death 1 ligand 1Homo sapiens (human)
negative regulation of activated T cell proliferationProgrammed cell death 1 ligand 1Homo sapiens (human)
negative regulation of tumor necrosis factor superfamily cytokine productionProgrammed cell death 1 ligand 1Homo sapiens (human)
positive regulation of activated CD8-positive, alpha-beta T cell apoptotic processProgrammed cell death 1 ligand 1Homo sapiens (human)
negative regulation of CD4-positive, alpha-beta T cell proliferationProgrammed cell death 1 ligand 1Homo sapiens (human)
negative regulation of CD8-positive, alpha-beta T cell activationProgrammed cell death 1 ligand 1Homo sapiens (human)
cellular response to lipopolysaccharideProgrammed cell death 1 ligand 1Homo sapiens (human)
negative regulation of T cell proliferationProgrammed cell death 1 ligand 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
protein bindingProgrammed cell death protein 1Homo sapiens (human)
signaling receptor activityProgrammed cell death protein 1Homo sapiens (human)
protein serine/threonine kinase activityAurora kinase BHomo sapiens (human)
protein serine/threonine kinase activityAurora kinase BHomo sapiens (human)
protein serine/threonine/tyrosine kinase activityAurora kinase BHomo sapiens (human)
protein bindingAurora kinase BHomo sapiens (human)
ATP bindingAurora kinase BHomo sapiens (human)
kinase bindingAurora kinase BHomo sapiens (human)
protein serine kinase activityAurora kinase BHomo sapiens (human)
transcription coactivator activityProgrammed cell death 1 ligand 1Homo sapiens (human)
protein bindingProgrammed cell death 1 ligand 1Homo sapiens (human)
receptor ligand activityProgrammed cell death 1 ligand 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (21)

Processvia Protein(s)Taxonomy
plasma membraneProgrammed cell death protein 1Homo sapiens (human)
external side of plasma membraneProgrammed cell death protein 1Homo sapiens (human)
kinetochoreAurora kinase BHomo sapiens (human)
condensed chromosome, centromeric regionAurora kinase BHomo sapiens (human)
nucleusAurora kinase BHomo sapiens (human)
nucleoplasmAurora kinase BHomo sapiens (human)
spindleAurora kinase BHomo sapiens (human)
cytosolAurora kinase BHomo sapiens (human)
chromocenterAurora kinase BHomo sapiens (human)
microtubule cytoskeletonAurora kinase BHomo sapiens (human)
midbodyAurora kinase BHomo sapiens (human)
chromosome passenger complexAurora kinase BHomo sapiens (human)
mitotic spindle poleAurora kinase BHomo sapiens (human)
mitotic spindle midzoneAurora kinase BHomo sapiens (human)
kinetochoreAurora kinase BHomo sapiens (human)
spindle pole centrosomeAurora kinase BHomo sapiens (human)
spindle microtubuleAurora kinase BHomo sapiens (human)
spindle midzoneAurora kinase BHomo sapiens (human)
nucleusProgrammed cell death 1 ligand 1Homo sapiens (human)
nucleoplasmProgrammed cell death 1 ligand 1Homo sapiens (human)
plasma membraneProgrammed cell death 1 ligand 1Homo sapiens (human)
actin cytoskeletonProgrammed cell death 1 ligand 1Homo sapiens (human)
early endosome membraneProgrammed cell death 1 ligand 1Homo sapiens (human)
recycling endosome membraneProgrammed cell death 1 ligand 1Homo sapiens (human)
extracellular exosomeProgrammed cell death 1 ligand 1Homo sapiens (human)
external side of plasma membraneProgrammed cell death 1 ligand 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (20)

Assay IDTitleYearJournalArticle
AID1801097Aurora B Kinase Assay from Article 10.1111/cbdd.12445: \\Plant-derived flavones as inhibitors of aurora B kinase and their quantitative structure-activity relationships.\\2015Chemical biology & drug design, May, Volume: 85, Issue:5
Plant-derived flavones as inhibitors of aurora B kinase and their quantitative structure-activity relationships.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
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.
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.
AID469266Antiinflammatory activity against mouse RAW264.7 cells assessed as inhibition of LPS-induced nitrite accumulation after 24 hrs by Griess reagent method2009Journal of natural products, Sep, Volume: 72, Issue:9
Triterpenoids and flavonoids from celery (Apium graveolens).
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.
AID1661026Inhibition of human PD1/PDL1 protein-protein interaction by HTRF assay
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (23)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (4.35)18.7374
1990's0 (0.00)18.2507
2000's8 (34.78)29.6817
2010's8 (34.78)24.3611
2020's6 (26.09)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 57.50

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index57.50 (24.57)
Research Supply Index3.18 (2.92)
Research Growth Index5.44 (4.65)
Search Engine Demand Index87.55 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (57.50)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (4.35%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other22 (95.65%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]