Compounds > tubulosine
Page last updated: 2024-12-06

tubulosine

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

Description

Tubulosine is a natural product that has been isolated from the Chinese medicinal plant *Tripterygium wilfordii*. It exhibits a range of biological activities, including anti-inflammatory, immunosuppressive, and anti-cancer effects. Its complex structure, composed of a highly modified indole alkaloid scaffold, has stimulated significant interest in its synthetic and medicinal chemistry. The compound is known to inhibit the activity of several enzymes, including protein kinases and DNA topoisomerases. Research into tubulosine is ongoing, with a focus on developing its potential as a therapeutic agent for various diseases.'

tubulosine: indole derivative of main alkaloids of ipecac; RN given refers to cpd with unspecified isomeric designation; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

tubulosine : A member of the class of beta-carbolines that is tubulosan bearing methoxy groups at positions 10 and 11 and a hydroxy group at the 8' position. [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 CID72341
CHEMBL ID518568
CHEBI ID9775
SCHEMBL ID1920742
MeSH IDM0054833

Synonyms (32)

Synonym
CHEBI:9775 ,
nsc-131547
1h-pyrido[3, 1-[[(2s,3r,11bs)-3-ethyl-1,3,4,6,7,11b-hexahydro- 9,10-dimethoxy-2h-benzo[a]quinolizin-2-yl]methyl]- 2,3,4,9-tetrahydro-, (1r)-
nsc131547 ,
tubulosan-8'-ol,11-dimethoxy-
10,11-dimethoxytubulosan-8'-ol
tubulosan-8'-ol, 10,11-dimethoxy-
1h-pyrido[3,4-b]indol-6-ol, 1-[[(2s,3r,11bs)-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2h-benzo[a]quinolizin-2-yl]methyl]-2,3,4,9-tetrahydro-, (1r)-
(1r)-1-[[(2s,3r,11bs)-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1h-benzo[a]quinolizin-2-yl]methyl]-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indol-6-ol
C09248
2632-29-3
tubulosine
(1r)-1-[[(2s,3r,11bs)-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1h-pyrido[2,1-a]isoquinolin-2-yl]methyl]-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indol-6-ol
NCI131547
NCI60_000694
NCISTRUC2_001820
NCISTRUC1_001471
SR-02000000201-1
CHEMBL518568
unii-112a6z7sn5
nsc 131547
10,11-dimethoxytubulosanol
112a6z7sn5 ,
SCHEMBL1920742
1h-pyrido(3,4-b)indol-6-ol, 1-((3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2h-benzo(a)quinolizin-2-yl)methyl)-2,3,4,9-tetrahydro-, (2s-(2.alpha.(s*),3.beta.,11b.beta.))-
(1r)-1-(((2s,3r,11bs)-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2h-benzo(a)quinolizin-2-yl)methyl)-2,3,4,9-tetrahydro-1h-pyrido(3,4-b)indol-6-ol
(-)-tubulosine
1h-pyrido(3,4-b)indol-6-ol, 1-(((2s,3r,11bs)-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2h-benzo(a)quinolizin-2-yl)methyl)-2,3,4,9-tetrahydro-, (1r)-
bdbm50480281
Q27108491
(1r)-1-[[(2s,3r,11bs)-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2h-benzo[a]quinolizin-2-yl]methyl]-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indol-6-ol
DTXSID701100319

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Dose-response experiments in primary cells confirmed pathway selectivity, but importantly also revealed differential inhibition of cell types and new druggability trends across multiple compounds."( High-content single-cell drug screening with phosphospecific flow cytometry.
Clutter, MR; Crane, JM; Krutzik, PO; Nolan, GP, 2008)		0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (6)

ClassDescription
isoquinoline alkaloidAny alkaloid that has a structure based on an isoquinoline nucleus. They are derived from the amino acids like tyrosine and phenylalanine.
secondary amino compoundA compound formally derived from ammonia by replacing two hydrogen atoms by organyl groups.
tertiary amino compoundA compound formally derived from ammonia by replacing three hydrogen atoms by organyl groups.
beta-carbolinesAny pyridoindole containing a beta-carboline skeleton and their hydrogenated derivatives
isoquinolinesA class of organic heteropolycyclic compound consisting of isoquinoline and its substitution derivatives.
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
[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 (27)

Assay IDTitleYearJournalArticle
AID376034Cytotoxicity against human multidrug resistant KB cells in presence of vinblastine1999Journal of natural products, Sep, Volume: 62, Issue:9
1',2',3',4'-tetradehydrotubulosine, a cytotoxic alkaloid from Pogonopus speciosus.
AID336511Antitumor activity against Agrobacterium tumefaciens-induced crown gall tumors in potato by disk test
AID376038Cytotoxicity against human SK-N-SH cells1999Journal of natural products, Sep, Volume: 62, Issue:9
1',2',3',4'-tetradehydrotubulosine, a cytotoxic alkaloid from Pogonopus speciosus.
AID376030Cytotoxicity against human BC1 cells1999Journal of natural products, Sep, Volume: 62, Issue:9
1',2',3',4'-tetradehydrotubulosine, a cytotoxic alkaloid from Pogonopus speciosus.
AID336510Toxicity in brine shrimp
AID376028In vivo antitumor activity against mouse L1210 cells assessed as increase in life span at 2 mg/kg1999Journal of natural products, Sep, Volume: 62, Issue:9
1',2',3',4'-tetradehydrotubulosine, a cytotoxic alkaloid from Pogonopus speciosus.
AID376033Cytotoxicity against human KB cells1999Journal of natural products, Sep, Volume: 62, Issue:9
1',2',3',4'-tetradehydrotubulosine, a cytotoxic alkaloid from Pogonopus speciosus.
AID397122Inhibition of HIV1 RT
AID1616252Cytotoxicity against human SKOV3 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay2019Journal of natural products, 09-27, Volume: 82, Issue:9
Octahydro-Protoberberine and Protoemetine-Type Alkaloids from the Stems of
AID1616250Cytotoxicity against human A549 cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay2019Journal of natural products, 09-27, Volume: 82, Issue:9
Octahydro-Protoberberine and Protoemetine-Type Alkaloids from the Stems of
AID495065Inhibition of JAK-mediated interferon-gamma-induced Stat1 phosphorylation in human U937 cells by Phospho-Flow cytometry at 20 uM2008Nature chemical biology, Feb, Volume: 4, Issue:2
High-content single-cell drug screening with phosphospecific flow cytometry.
AID376031Cytotoxicity against human Lu1 cells1999Journal of natural products, Sep, Volume: 62, Issue:9
1',2',3',4'-tetradehydrotubulosine, a cytotoxic alkaloid from Pogonopus speciosus.
AID376035Cytotoxicity against human multidrug resistant KB cells in absence of vinblastine1999Journal of natural products, Sep, Volume: 62, Issue:9
1',2',3',4'-tetradehydrotubulosine, a cytotoxic alkaloid from Pogonopus speciosus.
AID336513Cytotoxicity against human 9KB cells
AID336517In vivo antitumor activity against mouse 3PS cells at 0.25 mg/kg, relative to control
AID376037Cytotoxicity against human SW626 cells1999Journal of natural products, Sep, Volume: 62, Issue:9
1',2',3',4'-tetradehydrotubulosine, a cytotoxic alkaloid from Pogonopus speciosus.
AID376032Cytotoxicity against human Col2 cells1999Journal of natural products, Sep, Volume: 62, Issue:9
1',2',3',4'-tetradehydrotubulosine, a cytotoxic alkaloid from Pogonopus speciosus.
AID336512Cytotoxicity against mouse 9PS cells
AID376036Cytotoxicity against human LNCAP cells1999Journal of natural products, Sep, Volume: 62, Issue:9
1',2',3',4'-tetradehydrotubulosine, a cytotoxic alkaloid from Pogonopus speciosus.
AID336515Cytotoxicity against human MCF7 cells
AID1616251Cytotoxicity against human HeLa cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay2019Journal of natural products, 09-27, Volume: 82, Issue:9
Octahydro-Protoberberine and Protoemetine-Type Alkaloids from the Stems of
AID376039Cytotoxicity against mouse M109 cells1999Journal of natural products, Sep, Volume: 62, Issue:9
1',2',3',4'-tetradehydrotubulosine, a cytotoxic alkaloid from Pogonopus speciosus.
AID336514Cytotoxicity against human A549 cells
AID495066Inhibition of anisomycin-induced p38 phosphorylation in human U937 cells by Phospho-Flow cytometry at 20 uM2008Nature chemical biology, Feb, Volume: 4, Issue:2
High-content single-cell drug screening with phosphospecific flow cytometry.
AID376029In vivo antitumor activity against mouse P388 cells assessed as increase in life span at 2 mg/kg1999Journal of natural products, Sep, Volume: 62, Issue:9
1',2',3',4'-tetradehydrotubulosine, a cytotoxic alkaloid from Pogonopus speciosus.
AID495064Inhibition of JAK-mediated GM-CSF-induced Stat5 phosphorylation in human U937 cells by Phospho-Flow cytometry at 20 uM2008Nature chemical biology, Feb, Volume: 4, Issue:2
High-content single-cell drug screening with phosphospecific flow cytometry.
AID336516Cytotoxicity against human HT-29 cells
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (23.08)18.7374
1990's3 (23.08)18.2507
2000's4 (30.77)29.6817
2010's2 (15.38)24.3611
2020's1 (7.69)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.67

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 Index11.67 (24.57)
Research Supply Index2.83 (2.92)
Research Growth Index4.50 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.67)

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%
Other16 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
indirubin-3'-monoxime
indirubin-3'-monoxime: has antiangiogenic activity. indirubin-3'-monoxime : A member of the class of biindoles that is indirubin in which the keto group at position 3' has undergone condensation with hydroxylamine to form the corresponding oxime.		2.0410
1-(2-naphthalenyl)-2-propen-1-one
[no description available]		2.0410naphthalenes
patulin
Patulin: 4-Hydroxy-4H-furo(3,2-c)pyran-2(6H)-one. A mycotoxin produced by several species of Aspergillus and Penicillium. It is found in unfermented apple and grape juice and field crops. It has antibiotic properties and has been shown to be carcinogenic and mutagenic and causes chromosome damage in biological systems.. patulin : A furopyran and lactone that is (2H-pyran-3(6H)-ylidene)acetic acid which is substituted by hydroxy groups at positions 2 and 4 and in which the hydroxy group at position 4 has condensed with the carboxy group to give the corresponding bicyclic lactone. A mycotoxin produced by several species of Aspergillus and Penicillium, it has antibiotic properties but has been shown to be carcinogenic and mutagenic.		2.0410furopyran;
gamma-lactone;
lactol		antimicrobial agent;
Aspergillus metabolite;
carcinogenic agent;
mutagen;
mycotoxin;
Penicillium metabolite
streptonigrin
[no description available]		2.0410pyridines;
quinolone		antimicrobial agent;
antineoplastic agent
thymidine
[no description available]		1.9510pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
cycloheximide
Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.		1.9510antibiotic fungicide;
cyclic ketone;
dicarboximide;
piperidine antibiotic;
piperidones;
secondary alcohol		anticoronaviral agent;
bacterial metabolite;
ferroptosis inhibitor;
neuroprotective agent;
protein synthesis inhibitor
emetine
Emetine: The principal alkaloid of ipecac, from the ground roots of Uragoga (or Cephaelis) ipecacuanha or U. acuminata, of the Rubiaceae. It is used as an amebicide in many different preparations and may cause serious cardiac, hepatic, or renal damage and violent diarrhea and vomiting. Emetine inhibits protein synthesis in EUKARYOTIC CELLS but not PROKARYOTIC CELLS.. emetine : A pyridoisoquinoline comprising emetam having methoxy substituents at the 6'-, 7'-, 10- and 11-positions. It is an antiprotozoal agent and emetic. It inhibits SARS-CoV2, Zika and Ebola virus replication and displays antimalarial, antineoplastic and antiamoebic properties.		3.7100isoquinoline alkaloid;
pyridoisoquinoline		antiamoebic agent;
anticoronaviral agent;
antiinfective agent;
antimalarial;
antineoplastic agent;
antiprotozoal drug;
antiviral agent;
autophagy inhibitor;
emetic;
expectorant;
plant metabolite;
protein synthesis inhibitor
helenalin
helenalin: toxic principle of Helenium microcephalum (smallhead sneezeweed); structure. helenalin : A sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by a hydroxy group at position 4, methyl groups at positions 4a and 8 and a methylidene group at position 3 (the 3aS,4S,4aR,7aR,8R,9aR stereoisomer).. NF-kappaB inhibitor : An inhibitor of NF-kappaB (nuclear factor kappa-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.		2.0410cyclic ketone;
gamma-lactone;
organic heterotricyclic compound;
secondary alcohol;
sesquiterpene lactone		anti-inflammatory agent;
antineoplastic agent;
metabolite;
plant metabolite
Nanaomycin
[no description available]		2.0410benzoisochromanequinone
cephalotaxine
[no description available]		2.0410benzazepine alkaloid fundamental parent;
benzazepine alkaloid;
cyclic acetal;
enol ether;
organic heteropentacyclic compound;
secondary alcohol;
tertiary amino compound
nagilactone c
nagilactone C: norditerpene lactone isolated from leaves of Podocarpus; structure		2.0410
alantolactone
alantolactone: allergenic sesquiterpene lactone; crystalline mixture of alantolactones from group of sesquiterpenes; structure. alantolactone : A sesquiterpene lactone that is 3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2-one bearing two methyl substituents at positions 5 and 8a as well as a methylidene substituent at position 3.		2.0410naphthofuran;
olefinic compound;
sesquiterpene lactone		antineoplastic agent;
apoptosis inducer;
plant metabolite
streptovitacin a
streptovitacin A: structure		2.0410
cryptopleurine
cryptopleurine: plant bark alkaloid shown to inhibit protein synthesis; RN given refers to (R)-isomer; structure. cryptopleurine : An organic heteropentacyclic compound that is (14aR)-11,12,13,14,14a,15-hexahydro-9H-dibenzo[f,h]pyrido[1,2-b]isoquinoline substituted at positions 2, 3 and 6 by methoxy groups.		7.3620alkaloid antibiotic;
alkaloid;
aromatic ether;
organic heteropentacyclic compound		antineoplastic agent;
antiviral agent;
protein synthesis inhibitor
tylophorinidine
tylophorinidine: antileukemic agent from T. indica		710
sb 203580
[no description available]		2.0410imidazoles;
monofluorobenzenes;
pyridines;
sulfoxide		EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor;
EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor;
geroprotector;
Hsp90 inhibitor;
neuroprotective agent
anisomycin
Anisomycin: An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.. (-)-anisomycin : An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.		1.9510monohydroxypyrrolidine;
organonitrogen heterocyclic antibiotic		anticoronaviral agent;
antimicrobial agent;
antineoplastic agent;
antiparasitic agent;
bacterial metabolite;
DNA synthesis inhibitor;
protein synthesis inhibitor
hemanthamine
[no description available]		2.2110alkaloid
cephaelin
cephaelin: do not confuse with cephalin of brain; after emetine this is the most important alkaloid of ipecac; protein synthesis inhibitor. cephaeline : A pyridoisoquinoline comprising emetam having a hydroxy group at the 6'-position and methoxy substituents at the 7'-, 10- and 11-positions.		2.420pyridoisoquinoline
pergularinine
pergularinine: RN refers to (13aS-cis)-isomer; structure in first source		710
rottlerin
rottlerin: an angiogenesis inhibitor; an inhibitor of protein kinase Cdelta (PKCdelta) and calmodulin kinase III; RN refers to (E)-isomer; do not confuse this chalcone with an anthraquinone that is also called rottlerin (RN 481-72-1);. rottlerin : A chromenol that is 2,2-dimethyl-2H-chromene substituted by hydroxy groups at positions 5 and 7, a 3-acetyl-2,4,6-trihydroxy-5-methylbenzyl group at position 6 and a (1E)-3-oxo-1-phenylprop-1-en-3-yl group at position 8. A potassium channel opener, it is isolated from Mallotus philippensis.		2.0410aromatic ketone;
benzenetriol;
chromenol;
enone;
methyl ketone		anti-allergic agent;
antihypertensive agent;
antineoplastic agent;
apoptosis inducer;
K-ATP channel agonist;
metabolite
pactamycin
Pactamycin: Antibiotic produced by Streptomyces pactum used as an antineoplastic agent. It is also used as a tool in biochemistry because it inhibits certain steps in protein synthesis.		1.9510
2-tert-butyl-9-fluoro-3,6-dihydro-7h-benz(h)imidazo(4,5-f)isoquinoline-7-one
2-tert-butyl-9-fluoro-3,6-dihydro-7H-benz(h)imidazo(4,5-f)isoquinoline-7-one: a janus-activated kinase inhibitor. 2-tert-butyl-9-fluoro-1,6-dihydrobenzo[h]imidazo[4,5-f]isoquinolin-7-one : An organic heterotetracyclic compound that is 1,6-dihydrobenzo[h]imidazo[4,5-f]isoquinolin-7-one bearing additional tert-butyl and fluoro substituents at positions 2 and 9 respectively.		2.0410organic heterotetracyclic compound;
organofluorine compound		EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor
trichodermin
Trichodermin: Antifungal metabolite from several fungi, mainly Trichoderma viride; inhibits protein synthesis by binding to ribosomes; proposed as antifungal and antineoplastic; used as tool in cellular biochemistry.. trichodermin : A tetracyclic spiroepoxide which acts as an antifungal and protein synthesis inhibitor.		1.9510
sparsomycin
Sparsomycin: An antitumor antibiotic produced by Streptomyces sparsogenes. It inhibits protein synthesis in 70S and 80S ribosomal systems.		1.9510
phenanthrenes
Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.		1.9510
ConditionIndicatedRelationship StrengthStudiesTrials
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.0410
Necrosis
The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.		02.2510
Benign Neoplasms
[description not available]		0210
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		0210