Compounds > trilobacin
Page last updated: 2024-11-12

trilobacin

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Description

trilobacin: from the bark of Asimina triloba; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

trilobacin : A polyketide isolated from the bark of Asimina triloba. It has been shown to exhibit cytotoxicity in the NCI human tumor cell line screen. [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]

FloraRankFlora DefinitionFamilyFamily Definition
AsiminagenusA plant genus of the family ANNONACEAE. It has edible fruit and seeds which contain asitrocin, asitrilobins, and other tetrahydrofuran acetogenins.[MeSH]AnnonaceaeThe custard-apple plant family of the order Magnoliales, subclass Magnoliidae, class Magnoliopsida. Some members provide large pulpy fruits and commercial timber. Leaves and wood are often fragrant. Leaves are simple, with smooth margins, and alternately arranged in two rows along the stems.[MeSH]

Cross-References

ID SourceID
PubMed CID10416460
CHEMBL ID68179
CHEBI ID66270
MeSH IDM0201653

Synonyms (8)

Synonym
140224-67-5
CHEMBL68179
chebi:66270 ,
trilobacin
(5s)-3-[(2r,13r)-2,13-dihydroxy-13-{(2r,2's,5r,5'r)-5'-[(1r)-1-hydroxyundecyl]octahydro-2,2'-bifuran-5-yl}tridecyl]-5-methylfuran-2(5h)-one
(2s)-4-[(2r,13r)-2,13-dihydroxy-13-[(2r,5r)-5-[(2s,5r)-5-[(1r)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2h-furan-5-one
DTXSID401101051
(5s)-3-[(2r,13r)-2,13-dihydroxy-13-[(2r,2's,5r,5'r)-octahydro-5'-[(1r)-1-hydroxyundecyl][2,2'-bifuran]-5-yl]tridecyl]-5-methyl-2(5h)-furanone
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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 (3)

ClassDescription
polyketideNatural and synthetic compounds containing alternating carbonyl and methylene groups ('beta-polyketones'), biogenetically derived from repeated condensation of acetyl coenzyme A (via malonyl coenzyme A), and usually the compounds derived from them by further condensations, etc. Considered by many to be synonymous with the less frequently used terms acetogenins and ketides.
butenolideA gamma-lactone that consists of a 2-furanone skeleton and its substituted derivatives.
triolA chemical compound containing three hydroxy 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]

Bioassays (67)

Assay IDTitleYearJournalArticle
AID355174Toxicity to Artemia salina1996Journal of natural products, Nov, Volume: 59, Issue:11
Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba.
AID334402Growth inhibition of human NCI-H522 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334386Cytotoxicity against human MCF7 cells after 7 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334391Growth inhibition of human MOLT4 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334438Growth inhibition of human A498 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334429Growth inhibition of human UACC257 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334399Growth inhibition of human NCI-H23 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID355179Cytotoxicity against human PC3 cells after 7 days by MTT assay1996Journal of natural products, Nov, Volume: 59, Issue:11
Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba.
AID334432Growth inhibition of human OVCAR-3 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334413Growth inhibition of human SW620 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334385Toxicity against brine shrimp larvae1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334390Growth inhibition of human K562 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334388Growth inhibition of human CCRF-CEM cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334384Cytotoxicity against human A549 cells after 7 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334440Growth inhibition of human RXF631 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334439Growth inhibition of human Caki1 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334431Growth inhibition of human IGROV1 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID355178Cytotoxicity against human A498 cells after 7 days by MTT assay1996Journal of natural products, Nov, Volume: 59, Issue:11
Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba.
AID334426Growth inhibition of human SK-MEL-2 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID355175Cytotoxicity against human A549 cells after 7 days by MTT assay1996Journal of natural products, Nov, Volume: 59, Issue:11
Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba.
AID334394Growth inhibition of human A549 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334425Growth inhibition of human M19-MEL cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334434Growth inhibition of human OVCAR5 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334398Growth inhibition of human NCI-H226 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334404Growth inhibition of human DMS114 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334416Growth inhibition of human SF539 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID355176Cytotoxicity against human MCF7 cells after 7 days by MTT assay1996Journal of natural products, Nov, Volume: 59, Issue:11
Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba.
AID334442Growth inhibition of human TK10 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334433Growth inhibition of human OVCAR4 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334392Growth inhibition of human RPMI8266 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID355177Cytotoxicity against human HT29 cells after 7 days by MTT assay1996Journal of natural products, Nov, Volume: 59, Issue:11
Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba.
AID334395Growth inhibition of human EKVX cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334423Growth inhibition of human MALME-3M cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334409Growth inhibition of human HCT116 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334427Growth inhibition of human SK-MEL-28 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334435Growth inhibition of human OVCAR8 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334403Growth inhibition of human LXFL529 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334422Growth inhibition of human LOXIMVI cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334424Growth inhibition of human M14 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID15472Bullaticin index relates the IC50 values by normalizing to the value of bullatacin for easy comparison.1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
Structure-activity relationships of diverse Annonaceous acetogenins against multidrug resistant human mammary adenocarcinoma (MCF-7/Adr) cells.
AID355180Cytotoxicity against human MIAPaCa2 cells after 7 days by MTT assay1996Journal of natural products, Nov, Volume: 59, Issue:11
Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba.
AID334443Growth inhibition of human UO31 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334412Growth inhibition of human KM20L2 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334420Growth inhibition of human U251 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID103092Cytotoxicity against MCF-7/Adr cells.1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
Structure-activity relationships of diverse Annonaceous acetogenins against multidrug resistant human mammary adenocarcinoma (MCF-7/Adr) cells.
AID334401Growth inhibition of human NCI-H460 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID15625Statistical significance of IC 50 values; Expressed as R value1997Journal of medicinal chemistry, Jun-20, Volume: 40, Issue:13
Structure-activity relationships of diverse Annonaceous acetogenins against multidrug resistant human mammary adenocarcinoma (MCF-7/Adr) cells.
AID334418Growth inhibition of human SNB75 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334393Growth inhibition of human SR cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334397Growth inhibition of human HOP92 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334405Growth inhibition of human DMS273 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334400Growth inhibition of human NCI-H322M cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334396Growth inhibition of human HOP62 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334389Growth inhibition of human HL-60(TB) cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334428Growth inhibition of human SK-MEL-5 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334437Growth inhibition of human 786-0 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334406Growth inhibition of human COLO205 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334441Growth inhibition of human SN12C cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334414Growth inhibition of human SF268 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334421Growth inhibition of human XF498 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334387Cytotoxicity against human HT-29 cells after 7 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334436Growth inhibition of human SKOV3 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334411Growth inhibition of human HT-29 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334408Growth inhibition of human HCC2998 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334419Growth inhibition of human SNB78 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334430Growth inhibition of human UACC62 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
AID334407Growth inhibition of human DLD1 cells after 3 days1992Journal of natural products, Mar, Volume: 55, Issue:3
Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's4 (80.00)18.2507
2000's0 (0.00)29.6817
2010's1 (20.00)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: 12.40

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 Index12.40 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.20 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.40)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
vincristine
[no description available]		1.9910acetate ester;
formamides;
methyl ester;
organic heteropentacyclic compound;
organic heterotetracyclic compound;
tertiary alcohol;
tertiary amino compound;
vinca alkaloid		antineoplastic agent;
drug;
microtubule-destabilising agent;
plant metabolite;
tubulin modulator
4-butyrolactone
4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.		1.9910butan-4-olidemetabolite;
neurotoxin
vinblastine
[no description available]		1.9910
desacetyluvaricin
desacetyluvaricin: isolated from Uvaria accuminata; structure given in first source		1.9910
syringaresinol
(+)-syringaresinol : The (7alpha,7'alpha,8alpha,8'alpha)-stereoisomer of syringaresinol.		1.9810syringaresinolantineoplastic agent
feruloyltyramine
feruloyltyramine: structure given in first source; isolated from Cannabis sativa seeds, roots, leaves, and resin; induces hypothermia and motor incoordination in mice; moupinamide is (E)-isomer		1.9810tyraminesmetabolite
n-(4-hydroxy-beta-phenethyl)-4-hydroxycinnamide
trans-N-p-coumaroyl tyramine: from the twigs of Celtis chinensis; structure in first source		1.9810hydroxycinnamic acidmetabolite
10-hydroxyasimicin
10-hydroxyasimicin: a bis-tetrahydrofuran acetogenin with 4 hydroxyl groups; from Asimina triloba; structure given in first source		1.9910
ConditionIndicatedRelationship StrengthStudiesTrials
Adenocarcinoma, Basal Cell
[description not available]		01.9910
Breast Cancer
[description not available]		01.9910
Adenocarcinoma
A malignant epithelial tumor with a glandular organization.		01.9910
Breast Neoplasms
Tumors or cancer of the human BREAST.		01.9910