Page last updated: 2024-11-11

tautomycetin

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

Description

tautomycetin: isolated from Streptomyces griseochromogenes [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID6439037
CHEBI ID185968
MeSH IDM0163697

Synonyms (12)

Synonym
3-furanpropanoic acid, 2,5-dihydro-beta-hydroxy-4-methyl-2,5-dioxo-, 16-ethyl-3,7-dihydroxy-1,2,6,10,12-pentamethyl-5,14-dioxo-15,17-octadecadienyl ester
tautomycetin
119757-73-2
CHEBI:185968
[(16e)-17-ethyl-4,8-dihydroxy-3,7,11,13-tetramethyl-6,15-dioxononadeca-16,18-dien-2-yl] 3-hydroxy-3-(4-methyl-2,5-dioxouran-3-yl)propanoate
[(16e)-17-ethyl-4,8-dihydroxy-3,7,11,13-tetramethyl-6,15-dioxononadeca-16,18-dien-2-yl] 3-hydroxy-3-(4-methyl-2,5-dioxofuran-3-yl)propanoate
AKOS025294152
(1r*,2s*)-16-ethyl-3,7-dihydroxy-1,2,6,10,12-pentamethyl-5,14-dioxo-15,17-octadecadienyl 2,5-dihydro-beta-hydroxy-4-methyl-2,5-dioxo-3-furanpropanoic ac
3-furanpropanoic acid, 2,5-dihydro-beta-hydroxy-4-methyl-2,5-dioxo-, (1r,2s,6s,7s,10s,12r,15e)-16-ethyl-3,7-dihydroxy-1,2,6,10,12-pentamethyl-5,14-dioxo-15,17-octadecadien-1-yl ester, (betar)-
HY-108542
CS-0029112
AKOS040745384

Research Excerpts

Overview

Tautomycetin (TMC) is a linear polyketide metabolite produced by Streptomyces sp. It is a novel activated T-cell-specific immunosuppressive compound with a unique structure, containing an ester bond linkage between a terminal cyclic anhydride moiety and a linearpolyketide chain bearing an unusual terminal alkene.

ExcerptReferenceRelevance
"Tautomycetin (TTN) is a polyketide natural product featuring a terminal alkene. "( Biochemical and Structural Characterization of TtnD, a Prenylated FMN-Dependent Decarboxylase from the Tautomycetin Biosynthetic Pathway.
Annaval, T; Chang, CY; Crnovcic, I; Han, L; Ma, M; Miller, MD; Phillips, GN; Rudolf, JD; Shen, B; Soman, J; Xie, G; Xu, W; Yang, D, 2018
)
2.14
"Tautomycetin (TMC) is a linear polyketide metabolite produced by Streptomyces sp. "( Thioesterase domain swapping of a linear polyketide tautomycetin with a macrocyclic polyketide pikromycin in Streptomyces sp. CK4412.
Choi, SS; Kim, ES; Sherman, DH; Tripathi, A, 2016
)
2.13
"Tautomycetin (TMC) is a natural product with a linear structure that includes an ester bond connecting a dialkylmaleic moiety to a type I polyketide chain. "( Biosynthesis, regulation, and engineering of a linear polyketide tautomycetin: a novel immunosuppressant in Streptomyces sp. CK4412.
Choi, SS; Kim, ES; Nah, HJ; Pyeon, HR, 2017
)
2.14
"Tautomycetin (TMC) is a novel activated T-cell-specific immunosuppressive compound with a unique structure, containing an ester bond linkage between a terminal cyclic anhydride moiety and a linear polyketide chain bearing an unusual terminal alkene. "( Identification of TmcN as a pathway-specific positive regulator of tautomycetin biosynthesis in Streptomyces sp. CK4412.
Choi, SS; Hur, YA; Kim, ES; Sherman, DH, 2008
)
2.02
"Tautomycetin (TTN) is a highly potent and specific protein phosphatase inhibitor isolated from Streptomyces griseochromogenes. "( Characterization of the tautomycetin biosynthetic gene cluster from Streptomyces griseochromogenes provides new insight into dialkylmaleic anhydride biosynthesis.
Ju, J; Li, W; Luo, Y; Osada, H; Rajski, SR; Shen, B, 2009
)
2.1
"Tautomycetin (TMC) is a specific inhibitor of protein phosphatase 1, which has a role in cell-cycle control and T-cell activation and promotes T-cell-specific apoptosis."( The synergistic effect of Tautomycetin on Cyclosporine A-mediated immunosuppression in a rodent islet allograft model.
Choi, MY; Han, DJ; Kang, CH; Kim, JH; Kim, SC; Kim, YH; Lee, SK; Wee, YM; Yu, SY,
)
1.15
"Tautomycetin (TMC) is an unusual linear polyketide compound esterified with a cyclic anhydride. "( Identification and characterization of wblA-dependent tmcT regulation during tautomycetin biosynthesis in Streptomyces sp. CK4412.
Choi, SS; Kim, ES; Lee, CH; Nah, JH; Park, SH; Yoon, HM,
)
1.8
"Tautomycetin is a specific protein phosphatase I inhibitor. "( Functional characterization of the genes tauO, tauK, and tauI in the biosynthesis of tautomycetin.
Kong, R; Liu, B; Qiu, R; Tang, L; Wang, F; Zhao, J, 2012
)
2.05
"Tautomycetin is an antifungal antibiotic retaining potent immunosuppressive function. "( Tautomycetin inhibits growth of colorectal cancer cells through p21cip/WAF1 induction via the extracellular signal-regulated kinase pathway.
Choi, KY; Kim, SE; Kim, YC; Lee, JH; Lee, JS; Lee, SK; Moon, BS, 2006
)
3.22
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
sesquiterpenoidAny terpenoid derived from a sesquiterpene. The term includes compounds in which the C15 skeleton of the parent sesquiterpene has been rearranged or modified by the removal of one or more skeletal atoms (generally methyl groups).
[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]

Research

Studies (44)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (2.27)18.7374
1990's2 (4.55)18.2507
2000's20 (45.45)29.6817
2010's20 (45.45)24.3611
2020's1 (2.27)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 23.37

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 Index23.37 (24.57)
Research Supply Index3.85 (2.92)
Research Growth Index5.57 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (23.37)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews6 (13.04%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other40 (86.96%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]