Page last updated: 2024-12-07

terreic acid

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

Description

terreic acid: antibiotic metabolite of mold Aspergillus terreus; RN given refers to (1R)-isomer; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID91437
CHEMBL ID1455300
CHEBI ID156546
SCHEMBL ID51229
MeSH IDM0054047

Synonyms (43)

Synonym
HMS3267H06
terreic acid
NSC294734 ,
NCI60_002449
BIOMOLKI2_000077
(1r,6s)-3-hydroxy-4-methyl-7-oxabicyclo(4.1.0)hept-3-ene-2,5-dione
5,6-epoxy-3-hydroxy-p-toluquinone
(1r)-3-hydroxy-4-methyl-7-oxabicyclo(4.1.0)hept-3-ene-2,5-dione
7-oxabicyclo(4.1.0)hept-3-ene-2,5-dione, 3-hydroxy-4-methyl-, stereoisomer
nsc 294734
7-oxabicyclo(4.1.0)hept-3-ene-2,5-dione, 3-hydroxy-4-methyl-, (1r)-
2-hydroxy-3-methyl-1,4-benzoquinone 5,6-epoxide
3-hydroxy-4-methyl-7-oxabicyclo(4.1.0)hept-3-ene-2,5-dione
(-)-terreic acid
SMP2_000322
BIOMOLKI_000073
7-oxabicyclo[4.1.0]hept-3-ene-2, 3-hydroxy-4-methyl-, (1r-cis)-
nsc-294734
NCGC00025148-02
(1r,6s)-3-hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
CHEBI:156546
121-40-4
NCGC00025148-03
AKOS006281919
unii-xm2y0drj7d
xm2y0drj7d ,
CCG-100677
terreic acid [mi]
(5r),(6s)-epoxy-3-hydroxy-p-toluquinone
SCHEMBL51229
CHEMBL1455300
terreic acid (6ci)
7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione,3-hydroxy-4-methyl-,(1r,6s)-
sr-01000597558
SR-01000597558-1
(-)-terreic acid, synthetic - cas 121-40-4
HMS3676M22
HMS3412M22
Q27293905
DTXSID40879070
HY-110013
CS-0032828
(-)-terreicacid

Research Excerpts

Overview

Terreic acid is a metabolite with antibiotic properties produced by the fungus Aspergillus terreus. It is a natural product derived from 6-methylsalicylic acid (6-MSA)

ExcerptReferenceRelevance
"Terreic acid is a potential anticancer drug as it inhibits Bruton's tyrosine kinase; however, its biosynthetic molecular steps remain unclear. "( Heterologous pathway assembly reveals molecular steps of fungal terreic acid biosynthesis.
Cai, M; Huang, H; Kong, C; Liu, Q; Liu, Y; Peng, Q; Xu, Q; Xue, Y; Yin, Y; Zhang, Y; Zhou, X; Zhu, Q, 2018
)
2.16
"Terreic acid is a metabolite with antibiotic properties produced by the fungus Aspergillus terreus, but its cellular target remains unknown. "( Differential antibacterial properties of the MurA inhibitors terreic acid and fosfomycin.
Ingles, DJ; Olesen, SH; Schönbrunn, E; Yang, Y, 2014
)
2.09
"Terreic acid is a natural product derived from 6-methylsalicylic acid (6-MSA). "( Molecular genetic characterization of terreic acid pathway in Aspergillus terreus.
Bruno, KS; Guo, CJ; Sun, WW; Wang, CC, 2014
)
2.12
"Terreic acid is a metabolite with antibiotic properties produced by the fungus Aspergillus terreus. "( The fungal product terreic acid is a covalent inhibitor of the bacterial cell wall biosynthetic enzyme UDP-N-acetylglucosamine 1-carboxyvinyltransferase (MurA) .
Becker, A; Betzi, S; Han, H; Olesen, SH; Schönbrunn, E; Yang, Y, 2010
)
2.13

Actions

ExcerptReferenceRelevance
"Terreic acid was found to inhibit the acetyltransferase domain of E."( Escherichia coli N-Acetylglucosamine-1-Phosphate-Uridyltransferase/Glucosamine-1-Phosphate-Acetyltransferase (GlmU) Inhibitory Activity of Terreic Acid Isolated from Aspergillus terreus.
Chaubey, A; Chib, R; Jamwal, U; Khan, IA; Lambu, MR; Mukherjee, D; Rani, C; Sharma, R; Wazir, P, 2016
)
1.36
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (7)

RoleDescription
mycotoxinPoisonous substance produced by fungi.
antibacterial agentA substance (or active part thereof) that kills or slows the growth of bacteria.
EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitorAn EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of UDP-N-acetylglucosamine 1-carboxyvinyltransferase (EC 2.5.1.7).
EC 2.3.1.* (acyltransferase transferring other than amino-acyl group) inhibitorAn EC 2.3.* (acyltransferase) inhibitor that inhibits the action of any acyltransferase transferring groups other than amino-acyl groups (EC 2.3.1.*).
EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitorAn EC 2.7.10.* (protein-tyrosine kinase) inhibitor that specifically blocks the action of non-specific protein-tyrosine kinase (EC 2.7.10.2).
Aspergillus metaboliteAny fungal metabolite produced during a metabolic reaction in the mould, Aspergillus.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
[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 (4)

ClassDescription
arene epoxideAny epoxide formally derived from an arene by the 1,2 addition of an oxygen atom to a double bond.
tertiary alpha-hydroxy ketoneAn alpha-hydroxy ketone in which the carbonyl group and the hydroxy group are linked by a carbon bearing two organyl groups.
monohydroxy-1,4-benzoquinonesAny 1,4-benzoquinone carrying a single hydroxy substituent.
diketoneA compound that contains two ketone functionalities.
[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 (5)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
phosphopantetheinyl transferaseBacillus subtilisPotency56.23410.141337.9142100.0000AID1490
TDP1 proteinHomo sapiens (human)Potency19.47630.000811.382244.6684AID686978; AID686979
Microtubule-associated protein tauHomo sapiens (human)Potency17.90080.180013.557439.8107AID1460; AID1468
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency22.38720.035520.977089.1251AID504332
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency1.12200.354828.065989.1251AID504847
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID1347154Primary screen GU AMC 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.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (18)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (16.67)18.7374
1990's1 (5.56)18.2507
2000's1 (5.56)29.6817
2010's10 (55.56)24.3611
2020's3 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 24.01

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 Index24.01 (24.57)
Research Supply Index2.94 (2.92)
Research Growth Index5.31 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (24.01)

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%
Other18 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]