Compounds > betulonal
Page last updated: 2024-12-08

betulonal

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

Description

betulonal: originally isolated from white birch bark (Betula pendula); structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID473111
CHEMBL ID297478
SCHEMBL ID5956547
MeSH IDM000600147

Synonyms (22)

Synonym
(1r,3as,5ar,5br,7ar,11ar,11br,13ar,13br)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-9-oxo-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1h-cyclopenta[a]chrysene-3a-carbaldehyde
3,28-dideoxy-3,28-dioxobetulin
(1r,3as,4s,5ar,5br,7ar,11ar,11br,13ar,13br)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-9-oxo-eicosahydro-cyclopenta[a]chrysene-3a-carbaldehyde
CHEMBL297478
betulonic aldehyde
betulonal
(1r,3as,5ar,5br,7ar,11ar,11br,13ar,13br)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1h-cyclopenta[a]chrysene-3a-carbaldehyde
AKOS015959637
3-oxolup-20(29)-en-28-al
STL370357
SCHEMBL5956547
(1r,3as,5ar,5br,7ar,11ar,11br,13ar,13br)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-(prop-1-en-2-yl)icosahydro-1h-cyclopenta[a]chrysene-3 a-carbaldehyde
(1r,3as,5ar,5br,7ar,11ar,11br,13ar,13br)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-(prop-1-en-2-yl)icosahydro-1h-cyclopenta[a]chrysene-3a-carbaldehyde
MHAVMNJPXLZEIG-CNRMHUMKSA-N
4439-98-9
(1r,5ar,5br,7ar,11ar,11br,13ar,13br)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-9-oxoicosahydro-3ah-cyclopenta[a]chrysene-3a-carbaldehyde
betulonic aldehyde, betulonal
lup-20(29)-en-28-al-3-one
betulonaldehyde
nsc-818146
nsc818146
DTXSID301346531
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID95520Cytotoxicity against human epidermoid carcinoma of the mouth (KB) cell line.1998Bioorganic & medicinal chemistry letters, Jul-07, Volume: 8, Issue:13
Synthesis of betulinic acid derivatives with activity against human melanoma.
AID665419Solubility of the compound in water2012European journal of medicinal chemistry, Jul, Volume: 53Alkylidene branched lupane derivatives: synthesis and antitumor activity.
AID79295Anti-HIV activity against acutely infected H9 lymphocytes. Activity expressed as concentration of compound able to suppress HIV replication by 50%.1998Journal of medicinal chemistry, Nov-05, Volume: 41, Issue:23
Anti-AIDS agents. 34. Synthesis and structure-activity relationships of betulin derivatives as anti-HIV agents.
AID334273Induction of melanogenesis in mouse B16 2F2 cells assessed as intracellular melanin content after 3 days2002Journal of natural products, May, Volume: 65, Issue:5
Differentiation- and apoptosis-inducing activities by pentacyclic triterpenes on a mouse melanoma cell line.
AID1228703Cytotoxicity against mock-infected human MT2 cells assessed as reduction in cell viability incubated for 48 hrs by cell-titer Glo assay2015Journal of natural products, May-22, Volume: 78, Issue:5
Isolation, Structural Modification, and HIV Inhibition of Pentacyclic Lupane-Type Triterpenoids from Cassine xylocarpa and Maytenus cuzcoina.
AID210597Therapeutic Index is the average of the IC50 to that of EC501998Journal of medicinal chemistry, Nov-05, Volume: 41, Issue:23
Anti-AIDS agents. 34. Synthesis and structure-activity relationships of betulin derivatives as anti-HIV agents.
AID468093Antiviral activity against SFV infected in BHK cells after 14 hrs by luciferase reporter gene assay2009Journal of natural products, Nov, Volume: 72, Issue:11
Betulin-derived compounds as inhibitors of alphavirus replication.
AID468096Cytotoxicity against human HuH7 cells assessed as cell viability at 500 uM after 24 hrs2009Journal of natural products, Nov, Volume: 72, Issue:11
Betulin-derived compounds as inhibitors of alphavirus replication.
AID1228704Antiviral activity against HIV1 NL4.3-Ren infected in human MT2 cells assessed as inhibition of viral growth measured 48 hrs post infection by luminometry2015Journal of natural products, May-22, Volume: 78, Issue:5
Isolation, Structural Modification, and HIV Inhibition of Pentacyclic Lupane-Type Triterpenoids from Cassine xylocarpa and Maytenus cuzcoina.
AID79309Anti-HIV activity against acutely infected H9 lymphocytes. Activity expressed as concentration of compound toxic to 50% of mock-infected H9 cells.1998Journal of medicinal chemistry, Nov-05, Volume: 41, Issue:23
Anti-AIDS agents. 34. Synthesis and structure-activity relationships of betulin derivatives as anti-HIV agents.
AID1228705Selectivity index, ratio of CC50 for mock-infected human MT2 cells to IC50 for HIV1 NL4.3-Ren infected in human MT2 cells2015Journal of natural products, May-22, Volume: 78, Issue:5
Isolation, Structural Modification, and HIV Inhibition of Pentacyclic Lupane-Type Triterpenoids from Cassine xylocarpa and Maytenus cuzcoina.
AID334272Growth inhibition of mouse B16 2F2 cells after 3 days2002Journal of natural products, May, Volume: 65, Issue:5
Differentiation- and apoptosis-inducing activities by pentacyclic triterpenes on a mouse melanoma cell line.
AID468092Antiviral activity against SFV infected in BHK cells assessed as surviving virus fraction at 50 uM after 14 hrs by luciferase reporter gene assay2009Journal of natural products, Nov, Volume: 72, Issue:11
Betulin-derived compounds as inhibitors of alphavirus replication.
AID468095Cytotoxicity against human HuH7 cells assessed as cell viability at 50 uM after 24 hrs2009Journal of natural products, Nov, Volume: 72, Issue:11
Betulin-derived compounds as inhibitors of alphavirus replication.
AID106299Cytotoxicity against cultured human melanoma (MEL-2) cell line.1998Bioorganic & medicinal chemistry letters, Jul-07, Volume: 8, Issue:13
Synthesis of betulinic acid derivatives with activity against human melanoma.
AID1228702Antiviral activity against HIV1 NL4.3-Ren infected in human MT2 cells assessed as inhibition of viral growth at 10 uM measured 48 hrs post infection by luminometry2015Journal of natural products, May-22, Volume: 78, Issue:5
Isolation, Structural Modification, and HIV Inhibition of Pentacyclic Lupane-Type Triterpenoids from Cassine xylocarpa and Maytenus cuzcoina.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (25.00)18.2507
2000's2 (25.00)29.6817
2010's4 (50.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
acetone
methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).		2.1310ketone body;
methyl ketone;
propanones;
volatile organic compound		EC 3.5.1.4 (amidase) inhibitor;
human metabolite;
polar aprotic solvent
oleanolic acid
[no description available]		2.4520hydroxy monocarboxylic acid;
pentacyclic triterpenoid		plant metabolite
zidovudine
Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.		1.9910azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
ribavirin
Rebetron: Rebetron is tradename		2.05101-ribosyltriazole;
aromatic amide;
monocarboxylic acid amide;
primary carboxamide		anticoronaviral agent;
antiinfective agent;
antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
ursolic acid
[no description available]		2.0110hydroxy monocarboxylic acid;
pentacyclic triterpenoid		geroprotector;
plant metabolite
betulinic acid
[no description available]		2.9240hydroxy monocarboxylic acid;
pentacyclic triterpenoid		anti-HIV agent;
anti-inflammatory agent;
antimalarial;
antineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
plant metabolite
3'-amino-3'-deoxyadenosine
[no description available]		2.0510
betulin
betulin: isolated from various white birch bark (BETULA). betulin : A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-hydroxymethyl substituents.		3.2860diol;
pentacyclic triterpenoid		analgesic;
anti-inflammatory agent;
antineoplastic agent;
antiviral agent;
metabolite
beta-amyrin
beta-amyrin: alpha-amyrin is also available; a 5 ring triterpene derived from oleanane that differs from alpha-amyrin in having the 29-carbon at the 20 position; RN given refers to (3 beta)-isomer. beta-amyrin : A pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants.		2.0110pentacyclic triterpenoid;
secondary alcohol		Aspergillus metabolite;
plant metabolite
alpha-amyrin
alpha-amyrin: beta-amyrin is also available; a 5 ring triterpene derived from taraxasterol that differs from beta-amyrin in having the 29-carbon at the 19 position. alpha-amyrin : A pentacyclic triterpenoid that is ursane which contains a double bond between positions 12 and 13 and in which the hydrogen at the 3beta position is substituted by a hydroxy group.		2.0110pentacyclic triterpenoid;
secondary alcohol
betulinic acid methyl ester
betulinic acid methyl ester: from the roots of Saussurea lappa; structure in first source		2.7130triterpenoid
3-acetyllupeol
3-acetyllupeol: from root of Euphorbia fischeriana Steud; RN refers to (3beta)-isomer		2.0110organic molecular entitymetabolite
lupenone
lupenone: structure in first source		2.4520triterpenoidmetabolite
uvaol
uvaol: from Vauquelinia corymbosa (Rosaceae)		2.0110triterpenoidmetabolite
Lup-20(29)-en-28-al, 3beta-hydroxy-
[no description available]		2.4320triterpenoid
erythrodiol
[no description available]		2.0110diol;
pentacyclic triterpenoid;
primary alcohol;
secondary alcohol		plant metabolite
betulonic acid
betulonic acid: isolated from Rush javanica; strucure in first source		2.9640triterpenoidanticoronaviral agent
lupeol
[no description available]		2.7130pentacyclic triterpenoid;
secondary alcohol		anti-inflammatory drug;
plant metabolite
ochraceolide a
ochraceolide A: structure given in first source; isolated from Kokoona ochracea stem bark		2.1110
bevirimat
bevirimat: an HIV inhibitor; disrupts late step in processing HIV Major Core Protein p24, preventing the capsid precursor p25 from being converted to mature capsid p24. bevirimat : A pentacyclic triterpenoid obtained by the formal condensation of 2,2-dimethylsuccinic acid with the 3-hydroxy group of betulinic acid. It is isolated from the Chinese herb Syzygium claviflorum. The first in the class of HIV-1 maturation inhibitors to be studied in humans, bevirimat was identified as a potent HIV drug candidate and several clinical trials were conducted, but development into a new drug was plagued by numerous resistance-related problems.		2.4420dicarboxylic acid monoester;
monocarboxylic acid;
pentacyclic triterpenoid		HIV-1 maturation inhibitor;
metabolite
betulin-3-caffeate
betulin-3-caffeate: has antineoplastic activity; isolated from Hibiscus syriacus; structure in first source		2.1110
betulone
[no description available]		2.4520triterpenoidmetabolite
alpha-amyrenone
alpha-amyrenone: from Marsdenia officinalis Tsiang		2.0110
enfuvirtide
Enfuvirtide: A synthetic 36-amino acid peptide that corresponds to the heptad repeat sequence of HIV-1 gp41. It blocks HIV cell fusion and viral entry and is used with other anti-retrovirals for combination therapy of HIV INFECTIONS and AIDS.. enfuvirtide : A synthetic 36-amino acid peptide consisting of N-acetyltyrosyl, threonyl, seryl, leucyl, isoleucyl, histidyl, seryl, leucyl, isoleucyl, alpha-glutamyl, alpha-glutamyl, seryl, glutaminyl, asparaginyl, glutaminyl, glutaminyl, alpha-glutamyl, lysyl, asparaginyl, alpha-glutamyl, alpha-glutamyl, alpha-glutamyl, leucyl, leucyl, alpha-glutamyl, leucyl, alpha-aspartyl, lysyl, tryptophyl, alanyl, seryl, leucyl, tryptophyl, asparaginyl, tryptophyl, and phenylalaninamide residues joined in sequence. An HIV fusion inhibitor, it was the first of a novel class of antiretroviral drugs used in combination therapy for the treatment of HIV-1 infection. It interferes with entry of HIV into cells by binding to the gp41 sub-unit of the viral envelope glycoprotein, so inhibiting fusion of viral and cellular membranes.		1.9910
lupane
lupane: has antineoplastic activity; structure in first source		7.110
ConditionIndicatedRelationship StrengthStudiesTrials
Acquired Immune Deficiency Syndrome
[description not available]		01.9910
Acquired Immunodeficiency Syndrome
An acquired defect of cellular immunity associated with infection by the human immunodeficiency virus (HIV), a CD4-positive T-lymphocyte count under 200 cells/microliter or less than 14% of total lymphocytes, and increased susceptibility to opportunistic infections and malignant neoplasms. Clinical manifestations also include emaciation (wasting) and dementia. These elements reflect criteria for AIDS as defined by the CDC in 1993.		01.9910
Carcinoma, Epidermoid
[description not available]		01.9910
Malignant Melanoma
[description not available]		01.9910
Cancer of Mouth
[description not available]		01.9910
Carcinoma, Squamous Cell
A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)		01.9910
Melanoma
A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)		01.9910
Mouth Neoplasms
Tumors or cancer of the MOUTH.		01.9910
B16 Melanoma
[description not available]		02.0110