Compounds > heptaphylline
Page last updated: 2024-11-11

heptaphylline

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

Description

heptaphylline: cytotoxic carbazole alkaloid from the roots of Clausena harmandiana; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
ClausenagenusA plant genus of the family RUTACEAE. Members contain anethole and CARBAZOLES.[MeSH]RutaceaeA plant family in the order Sapindales that grows in warmer regions and has conspicuous flowers.[MeSH]

Cross-References

ID SourceID
PubMed CID5318015
CHEMBL ID1689799
CHEBI ID69927
MeSH IDM0556726

Synonyms (12)

Synonym
heptaphylline
2-hydroxy-1-(3-methylbut-2-enyl)-9h-carbazole-3-carbaldehyde
chebi:69927 ,
CHEMBL1689799
2-hydroxy-1-(3-methylbut-2-en-1-yl)-9h-carbazole-3-carbaldehyde
17750-35-5
3-formyl-2-hydroxy-1-prenylcarbazole
2-hydroxy-1-(3-methyl-2-butenyl)-9h-carbazole-3-carboxaldehyde, 9ci
2-hydroxy-1-(3-methyl-2-butenyl)-carbazole-3-carboxaldehyde
Q27138271
bdbm50496392
DTXSID301317762

Research Excerpts

Effects

ExcerptReferenceRelevance
"Heptaphylline has been shown to suppress the growth of different types of cancer cells. "( Heptaphylline suppresses the proliferation and migration of human bladder cancer cells via induction of intrinsic apoptosis, autophagy and inhibition of β-catenin signalling pathway.
Xu, A; Yang, GG; Zhang, Y; Zhao, ST, )		3.02
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[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 (1)

ClassDescription
carbazoles
[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 (20)

Assay IDTitleYearJournalArticle
AID664537Cytotoxicity against human KB cells by resazurin reduction assay2012Journal of natural products, Apr-27, Volume: 75, Issue:4
Bioactive carbazole alkaloids from Clausena wallichii roots.
AID664535Antibacterial activity against Escherichia coli TISTR 780 by broth dilution method2012Journal of natural products, Apr-27, Volume: 75, Issue:4
Bioactive carbazole alkaloids from Clausena wallichii roots.
AID613243Cytotoxicity against african green monkey Vero cells expressing green fluorescent protein after 4 days by fluorescence analysis2011European journal of medicinal chemistry, Sep, Volume: 46, Issue:9
Synthesis and cytotoxic activity of the heptaphylline and 7-methoxyheptaphylline series.
AID1075991Inhibition of BuChE in human serum using butyrylthiocholine iodide as substrate measured every 30s for 5 mins by Ellman's spectrophotometric method2014European journal of medicinal chemistry, Mar-21, Volume: 75Synthesis, biological evaluation and molecular modeling study of novel tacrine-carbazole hybrids as potential multifunctional agents for the treatment of Alzheimer's disease.
AID1075988Neuroprotective activity against H2O2-induced oxidative stress in mouse/rat NG108-15 cells assessed as cell viability at 100 uM incubated for 2 hrs prior to H2O2 challenge for 2 hrs by MTT assay2014European journal of medicinal chemistry, Mar-21, Volume: 75Synthesis, biological evaluation and molecular modeling study of novel tacrine-carbazole hybrids as potential multifunctional agents for the treatment of Alzheimer's disease.
AID1075993Antioxidant activity assessed as inhibition of ABTS radical cation formation after 15 mins by ABTS radical scavenging method2014European journal of medicinal chemistry, Mar-21, Volume: 75Synthesis, biological evaluation and molecular modeling study of novel tacrine-carbazole hybrids as potential multifunctional agents for the treatment of Alzheimer's disease.
AID587893Cytotoxicity against human NCI-H187 by resazurin microplate assay2011Journal of natural products, Feb-25, Volume: 74, Issue:2
Claurailas A-D, cytotoxic carbazole alkaloids from the roots of Clausena harmandiana.
AID587894Cytotoxicity against african green monkey Vero cells by green fluorescent protein microplate assay2011Journal of natural products, Feb-25, Volume: 74, Issue:2
Claurailas A-D, cytotoxic carbazole alkaloids from the roots of Clausena harmandiana.
AID664536Antibacterial activity against Salmonella typhimurium TISTR 292 by broth dilution method2012Journal of natural products, Apr-27, Volume: 75, Issue:4
Bioactive carbazole alkaloids from Clausena wallichii roots.
AID1075992Inhibition of electric eel acetylcholinesterase type VI-S using acetylthiocholine iodide as substrate measured every 30s for 5 mins by Ellman's spectrophotometric method2014European journal of medicinal chemistry, Mar-21, Volume: 75Synthesis, biological evaluation and molecular modeling study of novel tacrine-carbazole hybrids as potential multifunctional agents for the treatment of Alzheimer's disease.
AID664534Antibacterial activity against Staphylococcus aureus TISTR 1466 by broth dilution method2012Journal of natural products, Apr-27, Volume: 75, Issue:4
Bioactive carbazole alkaloids from Clausena wallichii roots.
AID1460596Cytotoxicity against African green monkey Vero cells assessed as reduction in cell viability after 72 hrs by tetrazolium dye assay2017Bioorganic & medicinal chemistry, 11-15, Volume: 25, Issue:22
Anti-tuberculosis activity and structure-activity relationships of oxygenated tricyclic carbazole alkaloids and synthetic derivatives.
AID664539Cytotoxicity against human NCI-H187 cells by resazurin reduction assay2012Journal of natural products, Apr-27, Volume: 75, Issue:4
Bioactive carbazole alkaloids from Clausena wallichii roots.
AID587892Cytotoxicity against human KB cells by resazurin microplate assay2011Journal of natural products, Feb-25, Volume: 74, Issue:2
Claurailas A-D, cytotoxic carbazole alkaloids from the roots of Clausena harmandiana.
AID1460595Antitubercular activity against Mycobacterium tuberculosis H37Rv by microplate alamar blue assay2017Bioorganic & medicinal chemistry, 11-15, Volume: 25, Issue:22
Anti-tuberculosis activity and structure-activity relationships of oxygenated tricyclic carbazole alkaloids and synthetic derivatives.
AID664538Cytotoxicity against human MCF7 cells by resazurin reduction assay2012Journal of natural products, Apr-27, Volume: 75, Issue:4
Bioactive carbazole alkaloids from Clausena wallichii roots.
AID1075986Neuroprotective activity against Abeta1-42 peptide-induced neurotoxicity in rat C6 cells assessed as cell viability at 100 uM after 24 hrs by MTT assay2014European journal of medicinal chemistry, Mar-21, Volume: 75Synthesis, biological evaluation and molecular modeling study of novel tacrine-carbazole hybrids as potential multifunctional agents for the treatment of Alzheimer's disease.
AID613241Cytotoxicity against human NCI-H187 cells after 5 days by resazurin microplate assay2011European journal of medicinal chemistry, Sep, Volume: 46, Issue:9
Synthesis and cytotoxic activity of the heptaphylline and 7-methoxyheptaphylline series.
AID613242Cytotoxicity against human KB cells after 3 days by resazurin microplate assay2011European journal of medicinal chemistry, Sep, Volume: 46, Issue:9
Synthesis and cytotoxic activity of the heptaphylline and 7-methoxyheptaphylline series.
AID664533Antibacterial activity against methicillin-resistant Staphylococcus aureus SK1 by broth dilution method2012Journal of natural products, Apr-27, Volume: 75, Issue:4
Bioactive carbazole alkaloids from Clausena wallichii roots.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's9 (81.82)24.3611
2020's2 (18.18)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.02

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 Index12.02 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index4.58 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.02)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (8.33%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (91.67%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
tacrine
Tacrine: A cholinesterase inhibitor that crosses the blood-brain barrier. Tacrine has been used to counter the effects of muscle relaxants, as a respiratory stimulant, and in the treatment of Alzheimer's disease and other central nervous system disorders.. tacrine : A member of the class of acridines that is 1,2,3,4-tetrahydroacridine substituted by an amino group at position 9. It is used in the treatment of Alzheimer's disease.		2.110acridines;
aromatic amine		EC 3.1.1.7 (acetylcholinesterase) inhibitor
ellipticine
ellipticine : A organic heterotetracyclic compound that is pyrido[4,3-b]carbazole carrying two methyl substituents at positions 5 and 11.		2.7630indole alkaloid;
organic heterotetracyclic compound;
organonitrogen heterocyclic compound;
polycyclic heteroarene		antineoplastic agent;
plant metabolite
isoniazid
Hydra: A genus of freshwater polyps in the family Hydridae, order Hydroida, class HYDROZOA. They are of special interest because of their complex organization and because their adult organization corresponds roughly to the gastrula of higher animals.. hydrazide : Compounds derived from oxoacids RkE(=O)l(OH)m (l =/= 0) by replacing -OH by -NRNR2 (R groups are commonly H). (IUPAC).		2.1510carbohydrazideantitubercular agent;
drug allergen
carbazole
carbazole: structure in first source		3.6520carbazole
pyrroles
1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.		3.1810pyrrole;
secondary amine
galantamine
Galantamine: A benzazepine derived from norbelladine. It is found in GALANTHUS and other AMARYLLIDACEAE. It is a cholinesterase inhibitor that has been used to reverse the muscular effects of GALLAMINE TRIETHIODIDE and TUBOCURARINE and has been studied as a treatment for ALZHEIMER DISEASE and other central nervous system disorders.. galanthamine : A benzazepine alkaloid isolated from certain species of daffodils.		2.110benzazepine alkaloid fundamental parent;
benzazepine alkaloid;
organic heterotetracyclic compound;
tertiary amino compound		antidote to curare poisoning;
cholinergic drug;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
plant metabolite
imperatorin
imperatorin: tumor necrosis factor antagonist; furanocoumarin from West African medicinal plant Clausena anisata; structure in Negwer, 5th ed, #3005. imperatorin : A member of the class of psoralens that is psoralen substituted by a prenyloxy group at position 8. Isolated from Angelica dahurica and Angelica koreana, it acts as a acetylcholinesterase inhibitor.		7.610psoralensEC 3.1.1.7 (acetylcholinesterase) inhibitor;
metabolite
indoline
indoline: structure given in first source		3.5920indoles
pentamethylbenzene
[no description available]		3.1810methylbenzene
vancomycin
Vancomycin: Antibacterial obtained from Streptomyces orientalis. It is a glycopeptide related to RISTOCETIN that inhibits bacterial cell wall assembly and is toxic to kidneys and the inner ear.. vancomycin : A complex glycopeptide from Streptomyces orientalis. It inhibits a specific step in the synthesis of the peptidoglycan layer in the Gram-positive bacteria Staphylococcus aureus and Clostridium difficile.		2.0710glycopeptideantibacterial drug;
antimicrobial agent;
bacterial metabolite
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid
[no description available]		2.110chromanol;
monocarboxylic acid;
phenols		antioxidant;
ferroptosis inhibitor;
neuroprotective agent;
radical scavenger;
Wnt signalling inhibitor
xanthoxyletin
xanthoxyletin: structure in first source		2.0610coumarinsmetabolite
murrayanine
murrayanine: carbazole alkaloid from Murraya koenigii; structure in first source		2.0610carbazolesmetabolite
girinimbine
girinimbine: carbazole alkaloid		2.4720carbazolesmetabolite
benzyne
benzyne: structure in first source. benzyne : 1,2-didehydrobenzene and its derivatives formed by substitution.		3.5920aryne;
benzyne
7-methoxyheptaphylline
7-methoxyheptaphylline: cytotoxic carbazole alkaloid from the roots of Clausena harmandiana; structure in first source		8.3460carbazolesmetabolite
dentatin
dentatin: from Clausena excavata; structure in first source		2.0610coumarinsmetabolite
methyl carbazole-3-carboxylate
methyl carbazole-3-carboxylate: structure in first source		2.0710carbazoles
clausine e
clausine E: structure in first source		2.0610carbazolesmetabolite
gentamicin sulfate
[no description available]		2.0710
warfarin
Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.		2.0610benzenes;
hydroxycoumarin;
methyl ketone
rifampin
Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)		2.1510cyclic ketal;
hydrazone;
N-iminopiperazine;
N-methylpiperazine;
rifamycins;
semisynthetic derivative;
zwitterion		angiogenesis inhibitor;
antiamoebic agent;
antineoplastic agent;
antitubercular agent;
DNA synthesis inhibitor;
EC 2.7.7.6 (RNA polymerase) inhibitor;
Escherichia coli metabolite;
geroprotector;
leprostatic drug;
neuroprotective agent;
pregnane X receptor agonist;
protein synthesis inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
Acute Confusional Senile Dementia
[description not available]		02.110
Age-Related Memory Disorders
[description not available]		02.110
Alzheimer Disease
A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)		02.110
Memory Disorders
Disturbances in registering an impression, in the retention of an acquired impression, or in the recall of an impression. Memory impairments are associated with DEMENTIA; CRANIOCEREBRAL TRAUMA; ENCEPHALITIS; ALCOHOLISM (see also ALCOHOL AMNESTIC DISORDER); SCHIZOPHRENIA; and other conditions.		02.110
Plasmodium falciparum Malaria
[description not available]		07.610
Malaria, Falciparum
Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.		02.610
Benign Neoplasms
[description not available]		02.3110
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.		02.3110
Adenocarcinoma, Basal Cell
[description not available]		02.110
Cancer of Colon
[description not available]		02.110
Adenocarcinoma
A malignant epithelial tumor with a glandular organization.		07.110
Colonic Neoplasms
Tumors or cancer of the COLON.		02.110