Compounds > chimaphilin
Page last updated: 2024-12-07

chimaphilin

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

Description

Chimaphilin is a natural product with a complex structure that has attracted significant interest due to its various biological activities, including antimicrobial, anti-inflammatory, and anticancer effects. It is found in the plant *Chimaphila umbellata*, commonly known as pipsissewa or prince's pine. The compound's biosynthesis involves a series of enzymatic reactions, starting with the precursor shikimic acid. Its unique structural features, including a fused bicyclic ring system and multiple oxygenated functional groups, contribute to its diverse pharmacological properties. Research on chimaphilin has focused on understanding its mechanisms of action, optimizing its synthesis, and exploring its potential therapeutic applications.'

chimaphilin: isolated from Chimaphila umbellata; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
Chimaphilagenus[no description available]EricaceaeThe heath plant family of the order Ericales, subclass Dilleniidae, class Magnoliopsida that are generally shrubs or small trees. Leaves are alternate, simple, and leathery; flowers are symmetrical with a 4- or 5-parted corolla of partly fused petals.[MeSH]

Cross-References

ID SourceID
PubMed CID101211
CHEMBL ID495277
CHEBI ID3595
SCHEMBL ID3141540
MeSH IDM0161513

Synonyms (27)

Synonym
NCI60_003733
nsc400245
1, 2,7-dimethyl-
nsc-400245
chimaphilin
482-70-2
chimaphylin
2,7-dimethylnaphthalene-1,4-dione
AC1L2QCI ,
2,7-dimethyl-1,4-naphthoquinone
chebi:3595 ,
CHEMBL495277
AKOS006271751
nsc 400245
u8z086618u ,
1,4-naphthalenedione, 2,7-dimethyl-
unii-u8z086618u
1,4-naphthoquinone, 2,7-dimethyl-
FT-0686583
chimaphilin [mi]
2,7-dimethyl-1,4-naphthalenedione
SCHEMBL3141540
DTXSID80197462
Q27106145
[(1-isobutylpiperidin-4-yl)methyl]methylamine
chimaphilin (6ci)
STARBLD0009547

Research Excerpts

Overview

Chimaphilin is a yellow naphthoquinone which occurs naturally in various chimaphila and Pyrola species.

ExcerptReferenceRelevance
"Chimaphilin is a yellow naphthoquinone which occurs naturally in various chimaphila and Pyrola species. "( The sensitizing capacity of chimaphilin, a naturally-occurring quinone.
Hausen, BM; Schiedermair, I, 1988)		2.01

Effects

ExcerptReferenceRelevance
"Chimaphilin has been demonstrated one of the major active components in Lu xian cao by modern pharmacological studies."( LC-MS method for determination and pharmacokinetic study of chimaphilin in rat plasma after oral administration of the traditional Chinese medicinal preparation Lu xian cao decoction.
Bi, K; Chen, X; Kim, C; Qin, S; Tebayashi, S; Zhang, Y, 2006)		1.3

Actions

Chimaphilin could inhibit the viability of MCF-7 cells in a concentration-dependent manner. It can increase the sensitivity of doxorubicin in osteosarcoma cell lines.

ExcerptReferenceRelevance
"Chimaphilin could inhibit the viability of MCF-7 cells in a concentration-dependent manner, and the IC50 value was 43.30μM for 24h."( Chimaphilin induces apoptosis in human breast cancer MCF-7 cells through a ROS-mediated mitochondrial pathway.
Duan, MH; Fu, YJ; Ma, WD; Sun, Y; Wang, P; Yao, XH; Yu, B; Zou, YP, 2014)		2.57
"Chimaphilin can increase the sensitivity of doxorubicin in doxorubicin-resistant osteosarcoma cell lines."( Chimaphilin inhibits proliferation and induces apoptosis in multidrug resistant osteosarcoma cell lines through insulin-like growth factor-I receptor (IGF-IR) signaling.
Chuandong, W; Daqian, W; Kerong, D; Songtao, A; Xinhua, Q, 2015)		2.58

Pharmacokinetics

ExcerptReferenceRelevance
" The method was successfully applied to pharmacokinetic study of chimaphilin in rat plasma following oral administration of a 30-mg/kg dose of chimaphilin in Lu xian cao decoction to male Wistar rats."( LC-MS method for determination and pharmacokinetic study of chimaphilin in rat plasma after oral administration of the traditional Chinese medicinal preparation Lu xian cao decoction.
Bi, K; Chen, X; Kim, C; Qin, S; Tebayashi, S; Zhang, Y, 2006)		0.81
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
1,4-naphthoquinonesA naphthoquinone in which the oxo groups of the quinone moiety are at positions 1 and 4 of the parent naphthalene 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 (19)

Assay IDTitleYearJournalArticle
AID400301Antimicrobial activity against Mycobacterium avium 724 ATCC 25291 at 100 ug/disk after 2 weeks by disk diffusion method1996Journal of natural products, Jan, Volume: 59, Issue:1
Chlorochimaphilin: a new antibiotic from Moneses uniflora.
AID400279Antimicrobial activity against Staphylococcus aureus SAP00017 after 24 hrs by twofold serial microbroth dilution assay1996Journal of natural products, Jan, Volume: 59, Issue:1
Chlorochimaphilin: a new antibiotic from Moneses uniflora.
AID401031Antimicrobial activity against Escherichia coli UB1005 after 24 hrs by twofold serial microbroth dilution assay1996Journal of natural products, Jan, Volume: 59, Issue:1
Chlorochimaphilin: a new antibiotic from Moneses uniflora.
AID400292Antimicrobial activity against Candida lipolytica after 48 hrs by twofold serial microbroth dilution assay1996Journal of natural products, Jan, Volume: 59, Issue:1
Chlorochimaphilin: a new antibiotic from Moneses uniflora.
AID400281Antimicrobial activity against Bacillus subtilis Vernon after 24 hrs by twofold serial microbroth dilution assay1996Journal of natural products, Jan, Volume: 59, Issue:1
Chlorochimaphilin: a new antibiotic from Moneses uniflora.
AID400291Antimicrobial activity against Candida albicans after 48 hrs by twofold serial microbroth dilution assay1996Journal of natural products, Jan, Volume: 59, Issue:1
Chlorochimaphilin: a new antibiotic from Moneses uniflora.
AID400296Antimicrobial activity against Aspergillus flavus after 48 hrs by twofold serial microbroth dilution assay1996Journal of natural products, Jan, Volume: 59, Issue:1
Chlorochimaphilin: a new antibiotic from Moneses uniflora.
AID401032Antimicrobial activity against Escherichia coli DC2 after 24 hrs by twofold serial microbroth dilution assay1996Journal of natural products, Jan, Volume: 59, Issue:1
Chlorochimaphilin: a new antibiotic from Moneses uniflora.
AID400297Antimicrobial activity against Aspergillus fumigatus after 48 hrs by twofold serial microbroth dilution assay1996Journal of natural products, Jan, Volume: 59, Issue:1
Chlorochimaphilin: a new antibiotic from Moneses uniflora.
AID400300Antimicrobial activity against Mycobacterium tuberculosis 107 ATCC 35801 at 100 ug/disk after 4 weeks by disk diffusion method1996Journal of natural products, Jan, Volume: 59, Issue:1
Chlorochimaphilin: a new antibiotic from Moneses uniflora.
AID400280Antimicrobial activity against Staphylococcus aureus RN4220 after 24 hrs by twofold serial microbroth dilution assay1996Journal of natural products, Jan, Volume: 59, Issue:1
Chlorochimaphilin: a new antibiotic from Moneses uniflora.
AID400298Antiviral activity against Herpes simplex virus 1 assessed as effect on virus-induced cytopathic effect at 200 ug/ml after 3 days1996Journal of natural products, Jan, Volume: 59, Issue:1
Chlorochimaphilin: a new antibiotic from Moneses uniflora.
AID400294Antimicrobial activity against Microsporum gypseum after 48 hrs by twofold serial microbroth dilution assay1996Journal of natural products, Jan, Volume: 59, Issue:1
Chlorochimaphilin: a new antibiotic from Moneses uniflora.
AID400299Antiviral activity against Respiratory syncytial virus assessed as effect on virus-induced cytopathic effect at 200 ug/ml after 3 days1996Journal of natural products, Jan, Volume: 59, Issue:1
Chlorochimaphilin: a new antibiotic from Moneses uniflora.
AID401033Antimicrobial activity against Pseudomonas aeruginosa K799 after 24 hrs by twofold serial microbroth dilution assay1996Journal of natural products, Jan, Volume: 59, Issue:1
Chlorochimaphilin: a new antibiotic from Moneses uniflora.
AID400293Antimicrobial activity against Saccharomyces cerevisiae after 48 hrs by twofold serial microbroth dilution assay1996Journal of natural products, Jan, Volume: 59, Issue:1
Chlorochimaphilin: a new antibiotic from Moneses uniflora.
AID401034Antimicrobial activity against Pseudomonas aeruginosa Z61 after 24 hrs by twofold serial microbroth dilution assay1996Journal of natural products, Jan, Volume: 59, Issue:1
Chlorochimaphilin: a new antibiotic from Moneses uniflora.
AID400282Antimicrobial activity against Candida albicans CAND105 after 48 hrs by twofold serial microbroth dilution assay1996Journal of natural products, Jan, Volume: 59, Issue:1
Chlorochimaphilin: a new antibiotic from Moneses uniflora.
AID400295Antimicrobial activity against Fusarium tricinctum after 48 hrs by twofold serial microbroth dilution assay1996Journal of natural products, Jan, Volume: 59, Issue:1
Chlorochimaphilin: a new antibiotic from Moneses uniflora.
[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-19902 (15.38)18.7374
1990's1 (7.69)18.2507
2000's5 (38.46)29.6817
2010's5 (38.46)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: 19.97

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

MetricThis Compound (vs All)
Research Demand Index19.97 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.97 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.97)

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%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
gallic acid
gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.		2.5220trihydroxybenzoic acidantineoplastic agent;
antioxidant;
apoptosis inducer;
astringent;
cyclooxygenase 2 inhibitor;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
geroprotector;
human xenobiotic metabolite;
plant metabolite
hydroquinone
[no description available]		6.9410benzenediol;
hydroquinones		antioxidant;
carcinogenic agent;
cofactor;
Escherichia coli metabolite;
human xenobiotic metabolite;
mouse metabolite;
skin lightening agent
propidium
Propidium: Quaternary ammonium analog of ethidium; an intercalating dye with a specific affinity to certain forms of DNA and, used as diiodide, to separate them in density gradients; also forms fluorescent complexes with cholinesterase which it inhibits.		2.110phenanthridines;
quaternary ammonium ion		fluorochrome;
intercalator
methicillin
Methicillin: One of the PENICILLINS which is resistant to PENICILLINASE but susceptible to a penicillin-binding protein. It is inactivated by gastric acid so administered by injection.. methicillin : A penicillin that is 6-aminopenicillanic acid in which one of the amino hydrogens is replaced by a 2,6-dimethoxybenzoyl group.		1.9910penicillin allergen;
penicillin		antibacterial drug
catechin
Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.		2.1110catechinantioxidant;
plant metabolite
hydrazine
diamine : Any polyamine that contains two amino groups.		2.0410azane;
hydrazines		EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
acetylcysteine
N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.		2.110acetylcysteine;
L-cysteine derivative;
N-acetyl-L-amino acid		antidote to paracetamol poisoning;
antiinfective agent;
antioxidant;
antiviral drug;
ferroptosis inhibitor;
geroprotector;
human metabolite;
mucolytic;
radical scavenger;
vulnerary
fluorescein-5-isothiocyanate
Fluorescein-5-isothiocyanate: Fluorescent probe capable of being conjugated to tissue and proteins. It is used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.. fluorescein 5-isothiocyanate : The 5-isomer of fluorescein isothiocyanate. Acts as a fluorescent probe capable of being conjugated to tissue and proteins; used as a label in fluorescent antibody staining procedures as well as protein- and amino acid-binding techniques.		2.110fluorescein isothiocyanate
monotropein
monotropein: isolated from the root of Morinda officinalis; structure in first source. monotropein : An iridoid monoterpenoid that is 1,4a,7,7a-tetrahydrocyclopenta[c]pyran substituted by a beta-D-glucopyranosyloxy group at position 1, a carboxylic acid group at position 4, and at position 7 by a hydroxy and hydroxymethyl groups respectively (the 1S,4aS,7R,7aS diastereomer).		2.0310beta-D-glucoside;
cyclopentapyran;
iridoid monoterpenoid;
monocarboxylic acid;
monosaccharide derivative		anti-inflammatory agent;
metabolite
uvaol
uvaol: from Vauquelinia corymbosa (Rosaceae)		2.0310triterpenoidmetabolite
arbutin
hydroquinone O-beta-D-glucopyranoside : A monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage.		2.1110beta-D-glucoside;
monosaccharide derivative		Escherichia coli metabolite;
plant metabolite
iridoids
Iridoids: A type of MONOTERPENES, derived from geraniol. They have the general form of cyclopentanopyran, but in some cases, one of the rings is broken as in the case of secoiridoid. They are different from the similarly named iridals (TRITERPENES).		2.0310
glycosides
[no description available]		6.9410
1,1-diphenyl-2-picrylhydrazyl
1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)		2.0410
naphthoquinones
Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.		3.89120
quercetin
[no description available]		2.52207-hydroxyflavonol;
pentahydroxyflavone		antibacterial agent;
antineoplastic agent;
antioxidant;
Aurora kinase inhibitor;
chelator;
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor;
geroprotector;
phytoestrogen;
plant metabolite;
protein kinase inhibitor;
radical scavenger
amphotericin b
Amphotericin B: Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela.. amphotericin B : A macrolide antibiotic used to treat potentially life-threatening fungal infections.		1.9910antibiotic antifungal drug;
macrolide antibiotic;
polyene antibiotic		antiamoebic agent;
antiprotozoal drug;
bacterial metabolite
hyperoside
quercetin 3-O-beta-D-galactopyranoside : A quercetin O-glycoside that is quercetin with a beta-D-galactosyl residue attached at position 3. Isolated from Artemisia capillaris, it exhibits hepatoprotective activity.		2.5220beta-D-galactoside;
monosaccharide derivative;
quercetin O-glycoside;
tetrahydroxyflavone		hepatoprotective agent;
plant metabolite
2''-galloylhyperin
2''-galloylhyperin: isolated from Pyrola calliantha		2.5220flavonoids;
glycoside
gentamicin sulfate
[no description available]		1.9910
nystatin a1
Nystatin: Macrolide antifungal antibiotic complex produced by Streptomyces noursei, S. aureus, and other Streptomyces species. The biologically active components of the complex are nystatin A1, A2, and A3.. nystatin : A heterogeneous mixture of polyene compounds produced by cultures of Streptomyces noursei. It mainly consists of three biologically active components designated nystatin A1, nystatin A2, and nystatin A3. It is used to treat oral and dermal fungal infections.. nystatin A1 : A polyene macrolide antibiotic; part of the nystatin complex produced by several Streptomyces species. It is an antifungal antibiotic used for the treatment of topical fungal infections caused by a broad spectrum of fungal pathogens comprising yeast-like and filamentous species.		1.9910nystatins
ConditionIndicatedRelationship StrengthStudiesTrials
Bone Cancer
[description not available]		02.1110
Osteogenic Sarcoma
[description not available]		02.5420
Bone Neoplasms
Tumors or cancer located in bone tissue or specific BONES.		02.1110
Osteosarcoma
A sarcoma originating in bone-forming cells, affecting the ends of long bones. It is the most common and most malignant of sarcomas of the bones, and occurs chiefly among 10- to 25-year-old youths. (From Stedman, 25th ed)		02.5420
Metastase
[description not available]		02.1710
Invasiveness, Neoplasm
[description not available]		02.1710
Neoplasm Metastasis
The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.		02.1710
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)		02.0310
Contact Dermatitis
[description not available]		01.9710
Dermatitis, Contact
A type of acute or chronic skin reaction in which sensitivity is manifested by reactivity to materials or substances coming in contact with the skin. It may involve allergic or non-allergic mechanisms.		01.9710