Compounds > tryprostatin b
Page last updated: 2024-12-11

tryprostatin b

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

Description

tryprostatin B: isolated from Aspergillus fumigatus; a mammalian cell cycle inhibitor; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

tryprostatin B : A cyclic dipeptide that is brevianamide F (cyclo-L-Trp-L-Pro) substituted at position 2 on the indole ring by a prenyl 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 CID9863281
CHEMBL ID36668
CHEBI ID72760
MeSH IDM0257175

Synonyms (12)

Synonym
triprostatin b
(3s,8as)-3-{[2-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
CHEMBL36668
chebi:72760 ,
tryprostatin b
C20512
(3s,8as)-3-((2-(3-methylbut-2-enyl)-1h-indol-3-yl)methyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
(3s,8as)-3-[[2-(3-methylbut-2-enyl)-1h-indol-3-yl]methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Q27140126
179936-52-8
(-)-tryprostatin b
DTXSID40893998
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (4)

ClassDescription
dipeptideAny molecule that contains two amino-acid residues connected by peptide linkages.
indolesAny compound containing an indole skeleton.
pyrrolopyrazine
indole alkaloidAn alkaloid containing an indole skeleton.
[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]

Pathways (2)

PathwayProteinsCompounds
fumitremorgin C biosynthesis518
superpathway of fumitremorgin biosynthesis925

Bioassays (43)

Assay IDTitleYearJournalArticle
AID327229Cytotoxicity against human DU145 cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID156012Growth inhibitory activity against PC-3 (human prostate) cancer cell line at 10 uM dose.2002Journal of medicinal chemistry, Apr-11, Volume: 45, Issue:8
Biological activity of the tryprostatins and their diastereomers on human carcinoma cell lines.
AID327212Cytotoxicity against human PC3 cells at 10 uM after 72 hrs by Cell Titer 96 Aqueous Non-Radioactive assay2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID423398Cytotoxicity against human MCF7 cells after 48 hrs by MTT assay2009Journal of natural products, Apr, Volume: 72, Issue:4
Bioactive alkaloids from endophytic Aspergillus fumigatus.
AID423396Cytotoxicity against human KB cells after 48 hrs by MTT assay2009Journal of natural products, Apr, Volume: 72, Issue:4
Bioactive alkaloids from endophytic Aspergillus fumigatus.
AID327232Cytotoxicity against human UO31 cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID1336111Inhibition of BCRP (unknown origin)-dependent ATPase activity at 50 uM after 30 mins by malachite green method2016Bioorganic & medicinal chemistry letters, 12-15, Volume: 26, Issue:24
Biosynthetic approaches to creating bioactive fungal metabolites: Pathway engineering and activation of secondary metabolism.
AID423397Cytotoxicity against human K562 cells after 48 hrs by MTT assay2009Journal of natural products, Apr, Volume: 72, Issue:4
Bioactive alkaloids from endophytic Aspergillus fumigatus.
AID327211Cytotoxicity against human MCF7 cells at 100 uM after 72 hrs by Cell Titer 96 Aqueous Non-Radioactive assay2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327220Cytotoxicity against human MOLT4 cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327210Cytotoxicity against human MCF7 cells at 10 uM after 72 hrs by Cell Titer 96 Aqueous Non-Radioactive assay2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327213Cytotoxicity against human PC3 cells at 100 uM after 72 hrs by Cell Titer 96 Aqueous Non-Radioactive assay2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327226Cytotoxicity against human HT29 cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID661416Cytotoxicity against human K562 cells after 72 hrs by MTT assay2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
Prenylation at the indole ring leads to a significant increase of cytotoxicity of tryptophan-containing cyclic dipeptides.
AID78422Growth inhibitory activity against H520 (human lung) cancer cell line at 10 uM dose2002Journal of medicinal chemistry, Apr-11, Volume: 45, Issue:8
Biological activity of the tryprostatins and their diastereomers on human carcinoma cell lines.
AID327231Cytotoxicity against human BT549 cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID103405Growth inhibitory activity against MCF-7 (human breast) cancer cell line at 100 uM dose.2002Journal of medicinal chemistry, Apr-11, Volume: 45, Issue:8
Biological activity of the tryprostatins and their diastereomers on human carcinoma cell lines.
AID1587848Cytotoxicity against mouse tsFT210 cells2019European journal of medicinal chemistry, Jun-01, Volume: 171Anti-tubulin agents of natural origin: Targeting taxol, vinca, and colchicine binding domains.
AID327240Cytotoxicity against human LOX IMVI cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327228Cytotoxicity against human IGROV1 cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327222Cytotoxicity against human SR cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID661415Cytotoxicity against mouse tsFT210 cells2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
Prenylation at the indole ring leads to a significant increase of cytotoxicity of tryptophan-containing cyclic dipeptides.
AID327224Cytotoxicity against human EKVX cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327217Cytotoxicity against human CCRF-CEM cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID78424Growth inhibitory activity against H520 (human lung) cancer cell line at 100 uM dose.2002Journal of medicinal chemistry, Apr-11, Volume: 45, Issue:8
Biological activity of the tryprostatins and their diastereomers on human carcinoma cell lines.
AID327218Cytotoxicity against human HL60 (TB) cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327223Cytotoxicity against human HOP92 cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327215Cytotoxicity against human MCF7 cells after 72 hrs by Cell Titer 96 Aqueous Non-Radioactive assay2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327216Cytotoxicity against human PC3 cells after 72 hrs by Cell Titer 96 Aqueous Non-Radioactive assay2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID661418Cytotoxicity against human cisplatin resistant A2780 cells after 72 hrs by MTT assay2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
Prenylation at the indole ring leads to a significant increase of cytotoxicity of tryptophan-containing cyclic dipeptides.
AID327208Cytotoxicity against human H520 cells at 10 uM after 72 hrs by Cell Titer 96 Aqueous Non-Radioactive assay2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327219Cytotoxicity against human K562 cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327225Cytotoxicity against human COLO205 cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID423399Induction of neurite outgrowth in rat PC12 cells at 10 uM after 2 days by phase-contrast microscope2009Journal of natural products, Apr, Volume: 72, Issue:4
Bioactive alkaloids from endophytic Aspergillus fumigatus.
AID156014Growth inhibitory activity against PC-3 (human prostate) cancer cell line at 100 uM dose.2002Journal of medicinal chemistry, Apr-11, Volume: 45, Issue:8
Biological activity of the tryprostatins and their diastereomers on human carcinoma cell lines.
AID327230Cytotoxicity against human MDA-MB-23212008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID661417Cytotoxicity against human cisplatin sensitive A2780 cells after 72 hrs by MTT assay2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
Prenylation at the indole ring leads to a significant increase of cytotoxicity of tryptophan-containing cyclic dipeptides.
AID327221Cytotoxicity against human RPMI8226 cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327206Inhibition of tubulin polymerization in presence of microtubule-associated proteins2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327209Cytotoxicity against human H520 cells at 100 uM after 72 hrs by Cell Titer 96 Aqueous Non-Radioactive assay2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID327227Cytotoxicity against human OVCAR-3 cells2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.
AID1336110Inhibition of BCRP in human K562 cells assessed as potentiation of SN38-mediated growth inhibition at 3 uM after 4 days by coulter counter method2016Bioorganic & medicinal chemistry letters, 12-15, Volume: 26, Issue:24
Biosynthetic approaches to creating bioactive fungal metabolites: Pathway engineering and activation of secondary metabolism.
AID103404Growth inhibitory activity against MCF-7 (human breast) cancer cell line at 10 uM dose.2002Journal of medicinal chemistry, Apr-11, Volume: 45, Issue:8
Biological activity of the tryprostatins and their diastereomers on human carcinoma cell lines.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (19)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's4 (21.05)18.2507
2000's9 (47.37)29.6817
2010's6 (31.58)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.47

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 Index11.47 (24.57)
Research Supply Index3.00 (2.92)
Research Growth Index4.47 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.47)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (10.53%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other17 (89.47%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
3,3-dimethylallyl pyrophosphate
3,3-dimethylallyl pyrophosphate: isomeric with isopentenyl pyrophosphate. prenyl diphosphate : A prenol phosphate that is a phosphoantigen comprising the O-pyrophosphate of prenol.		2.110prenol phosphateepitope;
Escherichia coli metabolite;
mouse metabolite;
phosphoantigen
alanine
Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.		7.0110alanine zwitterion;
alanine;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid		EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor;
fundamental metabolite
colchicine
(S)-colchicine : A colchicine that has (S)-configuration. It is a secondary metabolite, has anti-inflammatory properties and is used to treat gout, crystal-induced joint inflammation, familial Mediterranean fever, and many other conditions.		2.0410alkaloid;
colchicine		anti-inflammatory agent;
gout suppressant;
mutagen
tryptophan
Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.		7.0210erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid;
tryptophan zwitterion;
tryptophan		antidepressant;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
gramine
gramine : An aminoalkylindole that is indole carrying a dimethylaminomethyl substituent at postion 3.		7.2110aminoalkylindole;
indole alkaloid;
tertiary amino compound		antibacterial agent;
antiviral agent;
plant metabolite;
serotonergic antagonist
chloroprene
Chloroprene: Toxic, possibly carcinogenic, monomer of neoprene, a synthetic rubber; causes damage to skin, lungs, CNS, kidneys, liver, blood cells and fetuses. Synonym: 2-chlorobutadiene.		2.110chloroolefin
etoposide
[no description available]		2.0410beta-D-glucoside;
furonaphthodioxole;
organic heterotetracyclic compound		antineoplastic agent;
DNA synthesis inhibitor
fumitremorgin b
fumitremorgin B: intermediary in TR-2 mycotoxin biosyn; RN given refers to (5aR-(5aalpha,6alpha,12beta,14aalpha))-isomer; structure given in first source. fumitremorgin B : An organic heteropentacyclic compound that is a mycotoxic indole alkaloid produced by several fungi via a tryptophan-proline diketopiperazine intermediate.		3.2310indole alkaloid;
organic heteropentacyclic compound		mycotoxin
brevianamide f
brevianamide F: isolated from the endophyte from Aspergillus fumigatus associated with Melia azedarach L that could be used to develop a natural eco-friendly herbicide.structure in first source. brevianamide F : A pyrrolopyrazine that is hexahydropyrrolo[1,2-a]pyrazine-1,4-dione bearing an indol-3-ylmethyl substituent at position 3 (the 3S,8aS-diastereomer, obtained by formal cyclocondensation of L-tryptophan and L-proline).		3.8930dipeptide;
indoles;
pyrrolopyrazine		metabolite
tryptoquivaline
fumitremorgin C : An organic heteropentacyclic compound that is a mycotoxic indole alkaloid produced by several fungi. A potent and specific inhibitor of the breast cancer resistance protein multidrug transporter.		3.5820aromatic ether;
indole alkaloid;
organic heteropentacyclic compound		breast cancer resistance protein inhibitor;
mycotoxin
doxorubicin hydrochloride
[no description available]		2.0510anthracycline
cyclo(l-leucyl-l-tryptophyl)
cyclo(L-leucyl-L-tryptophyl): structure in first source		2.0710
centaureidin
centaureidin: structure given in first source; isolated from Tanacetum microphyllum, Brickellia veronicaefolia. centaureidin : A trihydroxyflavone that consists of quercetagetin in which the hydroxy groups at positions 3, 6 and 4' have been replaced by methoxy groups. It has been isolated from Eremophila mitchellii and Athroisma proteiforme.		3.3110trihydroxyflavone;
trimethoxyflavone		antineoplastic agent;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
plant metabolite
laulimalide
laulimalide: isolated from Cacospongia mycofijiensis; structure in first source. laulimalide : A macrolide with formula C30H42O7 that is isolated from the marine sponges, Cacospongia mycofijiensis and Hyattella sp.		3.3110carboxylic ester;
epoxide;
macrolide;
secondary alcohol;
secondary allylic alcohol		animal metabolite;
antimitotic;
antineoplastic agent;
marine metabolite;
microtubule-stabilising agent
cyclo(glycyltryptophyl)
cyclo(glycyltryptophyl): structure in first source		2.0710indolesmetabolite
(11S,14S)-Cyclo-(L-Trp-L-Phe)
[no description available]		2.0710indolesAspergillus metabolite
phenylahistin
phenylahistin: antineoplastic from Aspergillus ustus; structure in first source		3.3110
pseurotin
pseurotin: metabolite isolated from culture filtrates of Pseudeurotium ovalis Stolk; structure. pseurotin A : A spirocyclic that is 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione bearing 1,2-dihydroxyhex-3-en-1-yl, methyl, methoxy, benzoyl and hydroxy substituents at positions 2, 3, 8, 8 and 9 respectively.		2.0510azaspiro compound;
lactam;
oxaspiro compound		metabolite
tryprostatin a
tryprostatin A: isolated from Aspergillus fumigatus; a mammalian cell cycle inhibitor; structure given in first source. tryprostatin A : A cyclic dipeptide that is brevianamide F (cyclo-L-Trp-L-Pro) substituted at positions 2 and 6 on the indole ring by prenyl and methoxy groups respectively.		5.34100aromatic ether;
dipeptide;
indole alkaloid;
indoles;
pyrrolopyrazine		breast cancer resistance protein inhibitor
terpendole e
terpendole E: structure in first source		3.2310organic heterotricyclic compound;
organooxygen compound
demethoxyfumitremorgin c
demethoxyfumitremorgin C: isolated from the fermentation broth of Aspergillus fumigatus; a mammalian cell cycle inhibitor; structure given in first source. demethoxyfumitremorgin C : An organic heteropentacyclic compound that is a mycotoxic indole alkaloid, consisting of fumitremorgin C lacking the 9-methoxy substituent.		9.2150indole alkaloid;
organic heteropentacyclic compound		mycotoxin
spirotryprostatin a
spirotryprostatin A: structure in first source		2.0510
zampanolide
zampanolide: structure in first source		3.3110
verruculogen
verruculogen: complex 6-O-methylindole cpd containing 3 nitrogens; induces tremor; tremorigenic metabolite from Penicillium verruculosum isolated from moldy peanuts; decreases GABA levels in CNS; structure. verruculogen : An organic heterohexacyclic compound that is a mycotoxic indole alkaloid isolated from Penicillium and Aspergillus species.		3.2310aromatic ether;
diol;
indole alkaloid;
organic heterohexacyclic compound;
organic peroxide		Aspergillus metabolite;
GABA modulator;
mycotoxin;
Penicillium metabolite;
potassium channel blocker
cyclo(L-tryptophyl-L-alanyl)
[no description available]		2.07102,5-diketopiperazines
6-methoxyspirotryprostatin b
6-methoxyspirotryprostatin B: cytotoxic compound from the marine-derived fungus Aspergillus sydowi; structure in first source. 6-methoxyspirotryprostatin B : An indole alkaloid isolated from a marine-derived fungal strain Aspergillus sydowii PFW1-13 and has been shown to exhibit cytotoxic activity.		2.0510aromatic ether;
azaspiro compound;
indole alkaloid;
indolones		antineoplastic agent;
Aspergillus metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Breast Cancer
[description not available]		02.0410
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.0410