Page last updated: 2024-11-11

muconomycin a

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

Description

verrucarin A : A trichothecene antibiotic which incorporates a triester macrocyclic structure and an exocyclic methylene epoxide group. [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 CID6326658
CHEMBL ID136985
CHEBI ID230243
SCHEMBL ID108417
MeSH IDM0046831

Synonyms (29)

Synonym
nsc-126728
spiro(16,18-methano-1h,3h,23h-(1,6,12)trioxacyclooctadecino(3,4-d)(1)benzopyran-17(18h),2'-oxirane)-3,9,14-trione, 4,5,6,7,16,16a,19a,22-octahydro-4-hydroxy-5,16a,21-trimethyl-, stereoisomer
nsc 126728
ai3-29707
nsc 200736
(4s,5r,10e,12z,16r,16as,17s,18r,19ar,23ar)-4-hydroxy-5,16a,21-trimethyl-4,5,6,7,16,16a,22,23-octahydro-3h,18h,19ah-spiro[16,18-methano[1,6,12]trioxacyclooctadecino[3,4-d]chromene-17,2'-oxirane]-3,9,14-trione
nsc-200736
NSC200736 ,
ver a
379y
antibiotic 379y
3148-09-2
muconomycin a
verrucarin a
C09746
spiro(16,18-methano-1h,3h,23h-[1,6,12]trioxacyclooctadecino[3, 4-d](1)benzopyran-17(18h),2'-oxirane)-3,9,14-trione, 4,5,6,7,16, 16a,19a,22-octahydro-4-hydroxy-5,16a,21-trimethyl-, stereoisomer
chebi:230243 ,
CHEMBL136985
unii-ol62x66o4i
ol62x66o4i ,
SCHEMBL108417
verrucarine a
verrucarin a [mi]
spiro(16,18-methano-1h,3h,23h-(1,6,12)trioxacyclooctadecino(3,4-d)(1)benzopyran-17(18h),2'-oxirane)-3,9,14-trione, 4,5,6,7,16,16a,19a,22-octahydro-4-hydroxy-5,16a,21-trimethyl-, (4s,5r,10e,12z,16r,16as,17s,18r,19ar,23ar)-
3L2 ,
NLUGUZJQJYVUHS-IDXDZYHTSA-N
Q1586727
DTXSID101017607
(1r,3r,8r,12s,13r,18e,20z,24r,25s,26s)-12-hydroxy-5,13,25-trimethylspiro[2,10,16,23-tetraoxatetracyclo[22.2.1.03,8.08,25]heptacosa-4,18,20-triene-26,2'-oxirane]-11,17,22-trione

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"Trichothecene mycotoxins, toxic natural products of fungi from the family Hypocreaceae, are potent inhibitors of protein synthesis."( 3D QSAR study of the toxicity of trichothecene mycotoxins.
Lin, A; Rodarte, CB; Steinmetz, WE, 2009
)
0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (5)

ClassDescription
trichotheceneAny one of a large family of chemically related mycotoxins with a structure based on a sesquiterpene skeleton. The most important structural features causing the biological activities of trichothecenes are a 12,13-epoxy ring, the presence of hydroxy or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain.
macrolide antibioticA macrocyclic lactone with a ring of twelve or more members which exhibits antibiotic activity.
epoxideAny cyclic ether in which the oxygen atom forms part of a 3-membered ring.
macrotriolideA macropolylide which contains three ester linkages in one macrocyclic ring.
organic heterotetracyclic compound
[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 (42)

Assay IDTitleYearJournalArticle
AID334587Cytotoxicity against human primary soft tissue sarcoma cells after overnight incubation by Alamar blue assay2002Journal of natural products, May, Volume: 65, Issue:5
14'-Hydroxymytoxin B and 16-hydroxyroridin E, two new cytotoxic trichothecenes from Myrothecium roridum.
AID214739In vitro antitumor activity against melanoma UACC-62 tumor cell lines2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria.
AID378710Cytotoxicity against human BC1 cells1999Journal of natural products, Feb, Volume: 62, Issue:2
Antimalarial activity of macrocyclic trichothecenes isolated from the fungus Myrothecium verrucaria.
AID167407In vitro antitumor activity against renal RXF 393 tumor cell lines2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria.
AID103401In vitro antitumor activity against breast MCF-7 tumor cell lines2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria.
AID101978In vitro antitumor activity against breast MDA-MB-435 tumor cell lines2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria.
AID104211In vitro antitumor activity against melanoma M14 tumor cell lines2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria.
AID359205Cytotoxicity against mouse L1210 cells after 72 hrs by WST8 assay2001Journal of natural products, Mar, Volume: 64, Issue:3
A new macrocyclic trichothecene, 12,13-deoxyroridin E, produced by the marine-derived fungus Myrothecium roridum collected in Palau.
AID43645Selectivity was evaluated against Murine tumor ZC38 colon adenocarcinoma cell lines- ZL1210 lymphocytic leukemia cell lines at a concentration of 0.78 ug/mL2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria.
AID43362In vitro antitumor activity against leukemia CCRF-CEM tumor cell lines2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria.
AID9264In vitro antitumor activity against NSCL A549/ATCC tumor cell lines2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria.
AID378707Antimalarial activity against Plasmodium falciparum K1 by [3H]hypoxanthine uptake1999Journal of natural products, Feb, Volume: 62, Issue:2
Antimalarial activity of macrocyclic trichothecenes isolated from the fungus Myrothecium verrucaria.
AID201782In vitro antitumor activity against melanoma SK-MEL-2 tumor cell lines2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria.
AID112128Antileukemic activity in vivo against P-388 mouse leukemia cell expressed as Dose1980Journal of medicinal chemistry, Sep, Volume: 23, Issue:9
Antileukemic compounds derived from the chemical modification of macrocyclic trichothecenes. 1. Derivatives of verrucarin A.
AID79920Concentration giving 500 zone units against H116 colon tumor cell lines2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria.
AID153622In vivo activity against P388 mouse leukemia at a dose of 2 mg/kg1984Journal of medicinal chemistry, Feb, Volume: 27, Issue:2
Antileukemic compounds derived by chemical modification of macrocyclic trichothecenes. 2. Derivatives of roridins A and H and verrucarins A and J.
AID79921Activity relative to compound 3 (set to 1.0) was evaluated against H116 colon tumor cell lines2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria.
AID378712Cytotoxicity against african green monkey Vero cells1999Journal of natural products, Feb, Volume: 62, Issue:2
Antimalarial activity of macrocyclic trichothecenes isolated from the fungus Myrothecium verrucaria.
AID143326In vitro antitumor activity against NSCL NCI-H522 tumor cell lines2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria.
AID467616Antitumor activity against human leukemia cells xenografted in mouse assessed as logarithm of extension of mouse life span relative to untreated control2009European journal of medicinal chemistry, Nov, Volume: 44, Issue:11
3D QSAR study of the toxicity of trichothecene mycotoxins.
AID538369Cytotoxicity against human LNCAP cells2010Journal of medicinal chemistry, Nov-11, Volume: 53, Issue:21
Synthesis and biological analysis of prostate-specific membrane antigen-targeted anticancer prodrugs.
AID80066Selectivity was evaluated against human ZH125 lung non small cell carcinoma cell lines-CEM lymphocytic leukemia cell lines at a concentration of 0.78 ug/mL2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria.
AID359204Cytotoxicity against human HL60 cells after 72 hrs by WST8 assay2001Journal of natural products, Mar, Volume: 64, Issue:3
A new macrocyclic trichothecene, 12,13-deoxyroridin E, produced by the marine-derived fungus Myrothecium roridum collected in Palau.
AID378708Cytotoxicity against human KB cells1999Journal of natural products, Feb, Volume: 62, Issue:2
Antimalarial activity of macrocyclic trichothecenes isolated from the fungus Myrothecium verrucaria.
AID78602In vitro antitumor activity against colon HCT-15 tumor cell lines2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria.
AID8092In vitro antitumor activity against renal A498 tumor cell lines2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria.
AID1594686Cytotoxicity against human SW1116 cells by disk diffusion soft agar colony formation assay2019Journal of natural products, 06-28, Volume: 82, Issue:6
Cytotoxic Trichothecene Macrolides Produced by the Endophytic Myrothecium roridum.
AID46478In vitro antitumor activity against colon COLO 205 tumor cell lines2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria.
AID105098In vitro antitumor activity against leukemia MOLT-4 tumor cell lines2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria.
AID43506Selectivity was evaluated against murine tumor ZC38 colon adenocarcinoma cell lines- ZCFU-GM normal bone marrow cell lines at a concentration of 0.78 ug/mL2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria.
AID382886Toxicity in mouse CD4+ T cells assessed as induction of IL5 at 0.05 ng/ml2008Journal of natural products, Apr, Volume: 71, Issue:4
Structure and conformational dynamics of trichothecene mycotoxins.
AID382882Toxicity in ip dosed mouse2008Journal of natural products, Apr, Volume: 71, Issue:4
Structure and conformational dynamics of trichothecene mycotoxins.
AID79926Selectivity was evaluated against human ZH116 colon cell lines-CEM lymphocytic leukemia cell lines at a concentration of 0.78 ug/mL2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria.
AID80388In vitro antitumor activity against colon HCT116 tumor cell lines2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria.
AID82656In vitro antitumor activity against leukemia HL-60(TB) tumor cell lines2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria.
AID382884Toxicity in ip dosed mouse relative to roridin A2008Journal of natural products, Apr, Volume: 71, Issue:4
Structure and conformational dynamics of trichothecene mycotoxins.
AID144923In vitro antitumor activity against NSCL NCI-H226 tumor cell lines2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria.
AID105221In vitro antitumor activity against breast MDA-N tumor cell lines2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria.
AID1594685Cytotoxicity against human K562 cells by disk diffusion soft agar colony formation assay2019Journal of natural products, 06-28, Volume: 82, Issue:6
Cytotoxic Trichothecene Macrolides Produced by the Endophytic Myrothecium roridum.
AID467614Antitumor activity against human leukemia cells xenografted in mouse assessed as extension of mouse life span relative to untreated control2009European journal of medicinal chemistry, Nov, Volume: 44, Issue:11
3D QSAR study of the toxicity of trichothecene mycotoxins.
AID101424Selectivity was evaluated murine tumor against ZL1210 lymphocytic leukemia cell lines- ZCFU-GM normal bone marrow cell lines at a concentration of 0.78 ug/mL2003Journal of medicinal chemistry, Sep-25, Volume: 46, Issue:20
Structures and cytotoxic properties of trichoverroids and their macrolide analogues produced by saltwater culture of Myrothecium verrucaria.
AID120836Antileukemic activity in vivo against P-388 mouse leukemia(PS activity) and the T/C value was reported1980Journal of medicinal chemistry, Sep, Volume: 23, Issue:9
Antileukemic compounds derived from the chemical modification of macrocyclic trichothecenes. 1. Derivatives of verrucarin A.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (52)

TimeframeStudies, This Drug (%)All Drugs %
pre-199014 (26.92)18.7374
1990's12 (23.08)18.2507
2000's9 (17.31)29.6817
2010's16 (30.77)24.3611
2020's1 (1.92)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.54

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index10.54 (24.57)
Research Supply Index4.06 (2.92)
Research Growth Index4.60 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.54)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (1.75%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other56 (98.25%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]