Compounds > warburganal
Page last updated: 2024-11-06

warburganal

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

Warburganal is a natural product with a complex structure that has attracted significant attention due to its diverse biological activities. It was initially isolated from the bark of the African tree Warburgia ugandensis. Its synthesis is challenging due to the presence of multiple stereocenters and a highly oxygenated cyclohexane ring. Research on warburganal focuses on its potential as an anticancer agent, anti-inflammatory agent, and antimicrobial agent. Its anti-proliferative effects against various cancer cell lines have been investigated. The compound has also been shown to inhibit the production of inflammatory mediators and exhibit antibacterial activity against several strains of bacteria.'

Cross-References

ID SourceID
PubMed CID72502
CHEMBL ID452492
CHEBI ID10032
SCHEMBL ID4244667
MeSH IDM0112454

Synonyms (24)

Synonym
warburganal
C09748
62994-47-2
nsc-711690
nsc711690
(1s,4as,8as)-1-hydroxy-5,5,8a-trimethyl-4a,6,7,8-tetrahydro-4h-naphthalene-1,2-dicarbaldehyde
AC1L2I6T ,
(1s,4as,8as)-1-hydroxy-5,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalene-1,2-dicarbaldehyde
chebi:10032 ,
CHEMBL452492
AC1Q6A4Q ,
1,2-naphthalenedicarboxaldehyde, 1,4,4a,5,6,7,8,8a-octahydro-1-hydroxy-5,5,8a-trimethyl-, (1alpha,4aalpha,8abeta)-
4a48y1f67h ,
unii-4a48y1f67h
SCHEMBL4244667
warburganal [mi]
(1s,4as,8as)-1,4,4a,5,6,7,8,8a-octahydro-1-hydroxy-5,5,8a-trimethyl-1,2-naphthalenedicarboxaldehyde
(-)-warburganal
1,2-naphthalenedicarboxaldehyde, 1,4,4a,5,6,7,8,8a-octahydro-1-hydroxy-5,5,8a-trimethyl-, (1s-(1.alpha.,4a.alpha.,8a.beta.))-
1,2-naphthalenedicarboxaldehyde, 1,4,4a,5,6,7,8,8a-octahydro-1-hydroxy-5,5,8a-trimethyl-, (1s,4as,8as)-
warburganal, (-)-
DTXSID20212204
Q27108559
1r,4as,8as)-1-hydroxy-5,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalene-1,2-dicarbaldehyde
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
tertiary alcoholA tertiary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has three other carbon atoms attached to it.
[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 (30)

Assay IDTitleYearJournalArticle
AID359677Antimicrobial activity against Escherichia coli IFO 3545 after 2 days by twofold serial broth dilution method1993Journal of natural products, Sep, Volume: 56, Issue:9
Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.
AID338362Antimicrobial activity against Bacillus subtilis K-49 after 2 days
AID359678Antimicrobial activity against Bacillus subtilis ATCC 6633 after 2 days by twofold serial broth dilution method1993Journal of natural products, Sep, Volume: 56, Issue:9
Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.
AID359671Antimicrobial activity against Micrococcus luteus IFO 3333 after 2 days by twofold serial broth dilution method1993Journal of natural products, Sep, Volume: 56, Issue:9
Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.
AID359672Antimicrobial activity against Penicillium crustosum Thom after 2 days by twofold serial broth dilution method1993Journal of natural products, Sep, Volume: 56, Issue:9
Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.
AID359670Antimicrobial activity against Proteus vulgaris IAM 12003 after 2 days by twofold serial broth dilution method1993Journal of natural products, Sep, Volume: 56, Issue:9
Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.
AID338368Antimicrobial activity against Schizosaccharomyces pombe IFO 0342 after 2 days
AID338364Antimicrobial activity against Escherichia coli IFO 3545 after 2 days
AID359673Antimicrobial activity against Mucor mucedo IFO 7684 after 2 days by twofold serial broth dilution method1993Journal of natural products, Sep, Volume: 56, Issue:9
Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.
AID338360Antimicrobial activity against Hansenula anomala IFO 0136 after 2 days
AID359883Antimicrobial activity against Aspergillus niger ATCC 6275 after 2 days by twofold serial broth dilution method1993Journal of natural products, Sep, Volume: 56, Issue:9
Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.
AID359681Antimicrobial activity against Rhizopus chinensis IFO 4772 after 2 days by twofold serial broth dilution method1993Journal of natural products, Sep, Volume: 56, Issue:9
Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.
AID338366Antimicrobial activity against Pseudomonas aeruginosa IAM 1007 after 2 days
AID359674Antimicrobial activity against Candida utilis ATCC 42402 after 2 days by twofold serial broth dilution method1993Journal of natural products, Sep, Volume: 56, Issue:9
Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.
AID338372Antimicrobial activity against Rhizopus chinensis IFO 4745 after 2 days
AID359676Antimicrobial activity against Pseudomonas aeruginosa IAM 1007 after 2 days by twofold serial broth dilution method1993Journal of natural products, Sep, Volume: 56, Issue:9
Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.
AID338363Antimicrobial activity against Micrococcus lysodeikticus IFO 3333 after 2 days
AID338361Antimicrobial activity against Staphylococcus aureus NCTC 8530 after 2 days
AID338367Antimicrobial activity against Saccharomyces cerevisiae IFO 0203 after 2 days
AID359675Antimicrobial activity against Saccharomyces cerevisiae IFO 0203 after 2 days by twofold serial broth dilution method1993Journal of natural products, Sep, Volume: 56, Issue:9
Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.
AID338369Antimicrobial activity against Candida utilis ATCC 42402 after 2 days
AID338374Antimicrobial activity against Penicillium crustosum Thom after 2 days
AID359680Antimicrobial activity against Sclerotinia libertiana IFO 7684 after 2 days by twofold serial broth dilution method1993Journal of natural products, Sep, Volume: 56, Issue:9
Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.
AID338371Antimicrobial activity against Mucor mucedo IFO 7684 after 2 days
AID359679Antimicrobial activity against Staphylococcus aureus NCTC 8530 after 2 days by twofold serial broth dilution method1993Journal of natural products, Sep, Volume: 56, Issue:9
Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.
AID359668Antimicrobial activity against Schizosaccharomyces pombe IFO 0342 after 2 days by twofold serial broth dilution method1993Journal of natural products, Sep, Volume: 56, Issue:9
Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.
AID338373Antimicrobial activity against Aspergillus niger ATCC 6275 after 2 days
AID338370Antimicrobial activity against Sclerotinia libertiana SS after 2 days
AID359669Antimicrobial activity against Hansenula anomala IFO 0136 after 2 days by twofold serial broth dilution method1993Journal of natural products, Sep, Volume: 56, Issue:9
Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.
AID338365Antimicrobial activity against Proteus vulgaris IAM 12003 after 2 days
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (33.33)18.7374
1990's3 (50.00)18.2507
2000's0 (0.00)29.6817
2010's1 (16.67)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: 21.64

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 Index21.64 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.42 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.64)

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%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
polygodial
[no description available]		1.9810aldehyde
phaseollidin
phaseollidin: from Erythrina burana; RN refers to (6aR-cis)-isomer; structure given in first source. phaseollidin : A member of the class of pterocarpans that is (6aR,11aR)-pterocarpan substituted by hydroxy groups at positions 3 and 9 and a prenyl group at position 10.		1.9810pterocarpans
cristacarpin
cristacarpin: isolated from Erythrina burana; RN given refers to (6aS-cis)-isomer; structure given in first source		1.9810pterocarpans
sclareol
sclareol: structure given in first source. sclareol : A labdane diterpenoid that is labd-14-ene substituted by hydroxy groups at positions 8 and 13. It has been isolated from Salvia sclarea.		710labdane diterpenoidantifungal agent;
antimicrobial agent;
apoptosis inducer;
fragrance;
plant metabolite
benzofurans
Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.		210
abyssinone i
abyssinone I: anti-oxidant and cytotoxic compound from East African medicinal plant Erythrina abyssinica; structure in first source. abyssinone I : A monohydroxyflavanone that is (2S)-2',2'-dimethyl-2,3-dihydro-2'H,4H-2,6'-bichromen-4-one carrying a hydroxy substituent at position 7.		1.9810monohydroxyflavanone;
phenols		apoptosis inhibitor;
plant metabolite
abyssinone v
abyssinone V: isolated from Erythrina sigboidea; RN from Chemical Abstracts Index Guide; structure given in first source. abyssinone V : A trihydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 7 and 4' and prenyl groups at positions 3' and 5' respectively.		1.98104'-hydroxyflavanones;
phenols;
trihydroxyflavanone		metabolite
cinnamodial
cinnamodial: dialdehyde sesquiterpene; structure in first source		1.9810tertiary alcohol
anethole
anethole: an isomer of estragole; structurally similar to CAPSAICIN; has some neurological and insecticidal and skin absorption effects; RN given refers to unspecified stereoisomer. anethole : A monomethoxybenzene that is methoxybenzene substituted by a prop-1-en-1-yl group at position 4.. trans-anethole : The trans-stereoisomer of anethole.		1.9810anetholeflavouring agent
sesquiterpenes
[no description available]		3.0850
alpha-linolenic acid
linolenic acid : A two-membered subclass of octadecatrienoic acid comprising the (9Z,12Z,15Z)- and (6Z,9Z,12Z)-isomers. Linolenic acids are nutrients essential to the formation of prostaglandins and are also used in making paints and synthetic resins.. linolenate : A polyunsaturated fatty acid anion obtained by deprotonation of the carboxy group of either alpha- or gamma-linolenic acid.		2.1710linolenic acid;
omega-3 fatty acid		micronutrient;
mouse metabolite;
nutraceutical
cysteine
Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.		1.9610cysteiniumfundamental metabolite
ascorbic acid
Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.		1.9810ascorbic acid;
vitamin C		coenzyme;
cofactor;
flour treatment agent;
food antioxidant;
food colour retention agent;
geroprotector;
plant metabolite;
skin lightening agent
ConditionIndicatedRelationship StrengthStudiesTrials
Eczema, Atopic
[description not available]		01.9610
Contact Dermatitis
[description not available]		01.9610
Allergy, Drug
[description not available]		01.9610
Delayed Hypersensitivity
[description not available]		01.9610
Dermatitis, Atopic
A chronic inflammatory genetically determined disease of the skin marked by increased ability to form reagin (IgE), with increased susceptibility to allergic rhinitis and asthma, and hereditary disposition to a lowered threshold for pruritus. It is manifested by lichenification, excoriation, and crusting, mainly on the flexural surfaces of the elbow and knee. In infants it is known as infantile eczema.		01.9610
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.		01.9610
Drug Hypersensitivity
Immunologically mediated adverse reactions to medicinal substances used legally or illegally.		01.9610
Leukemia P388
An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.		0210