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4481-62-3,MFCD08459607
Catalog No.:AA00DA29

4481-62-3 | Betulonic acid

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5mg
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10mg
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25mg
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50mg
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500mg
98% by HPLC
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1000mg
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  • Technical Information
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  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00DA29
Chemical Name:
Betulonic acid
CAS Number:
4481-62-3
Molecular Formula:
C30H46O3
Molecular Weight:
454.6844
MDL Number:
MFCD08459607
SMILES:
CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)CCC(=O)C1(C)C)C(=O)O
Properties
Computed Properties
 
Complexity:
902  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
9  
Heavy Atom Count:
33  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
2  
XLogP3:
7.9  

Literature

Title: Ionic derivatives of betulinic acid exhibit antiviral activity against herpes simplex virus type-2 (HSV-2), but not HIV-1 reverse transcriptase.

Journal: Bioorganic & medicinal chemistry letters 20150815

Title: Betulin derivatives impair Leishmania braziliensis viability and host-parasite interaction.

Journal: Bioorganic & medicinal chemistry 20141101

Title: X-ray diffraction and infrared spectroscopy of N,N-dimethylformamide and dimethyl sulfoxide solvatomorphs of betulonic acid.

Journal: Journal of pharmaceutical sciences 20121201

Title: A practical synthesis of betulonic acid using selective oxidation of betulin on aluminium solid support.

Journal: Molecules (Basel, Switzerland) 20121009

Title: Effect of triterpene derivatives on the total hepatocyte count in the liver of rats with toxic hepatitis.

Journal: Bulletin of experimental biology and medicine 20121001

Title: Alkylidene branched lupane derivatives: synthesis and antitumor activity.

Journal: European journal of medicinal chemistry 20120701

Title: Cytotoxic heterocyclic triterpenoids derived from betulin and betulinic acid.

Journal: Bioorganic & medicinal chemistry 20120601

Title: Study of skin anti-ageing and anti-inflammatory effects of dihydroquercetin, natural triterpenoids, and their synthetic derivatives.

Journal: Bioorganicheskaia khimiia 20120101

Title: Synthesis and evaluation of library of betulin derivatives against the botulinum neurotoxin A protease.

Journal: Bioorganic & medicinal chemistry letters 20110415

Title: Development of a new HPLC method with precolumn fluorescent derivatization for rapid, selective and sensitive detection of triterpenic acids in fruits.

Journal: Journal of agricultural and food chemistry 20110413

Title: Rapid access to new bioconjugates of betulonic acid via click chemistry.

Journal: Bioorganic & medicinal chemistry letters 20110101

Title: [Synthesis of A-secomethylenamino- and substituted amidoximotriterpenoids].

Journal: Bioorganicheskaia khimiia 20110101

Title: Ixorapeptide I and ixorapeptide II, bioactive peptides isolated from Ixora coccinea.

Journal: Bioorganic & medicinal chemistry letters 20101215

Title: Structure of the liver in mice with transplanted Lewis carcinoma during polychemotherapy and correction with betulonic acid and its derivatives.

Journal: Bulletin of experimental biology and medicine 20101201

Title: Small structural changes of pentacyclic lupane type triterpenoid derivatives lead to significant differences in their anticancer properties.

Journal: European journal of medicinal chemistry 20100801

Title: Anti-leishmanial activity of betulin derivatives.

Journal: The Journal of antibiotics 20100301

Title: Structure-activity relationship study of betulinic acid, a novel and selective TGR5 agonist, and its synthetic derivatives: potential impact in diabetes.

Journal: Journal of medicinal chemistry 20100114

Title: Betulin-derived compounds as inhibitors of alphavirus replication.

Journal: Journal of natural products 20091101

Title: Rational design and semisynthesis of betulinic acid analogues as potent topoisomerase inhibitors.

Journal: Journal of natural products 20090901

Title: Efficient synthesis of the first betulonic acid-acetylene hybrids and their hepatoprotective and anti-inflammatory activity.

Journal: Bioorganic & medicinal chemistry 20090715

Title: [Betulonic amides modified at the ring A by amino acids: synthesis and inhibition of influenza A virus reproduction].

Journal: Bioorganicheskaia khimiia 20090101

Title: [Synthesis and modification of triterpenoids with two lupan backbones].

Journal: Bioorganicheskaia khimiia 20090101

Title: Cardiomyocyte count in rat myocardium under the effect of antitumor agents cyclophosphamide and triterpenoids.

Journal: Bulletin of experimental biology and medicine 20070901

Title: Specific plant terpenoids and lignoids possess potent antiviral activities against severe acute respiratory syndrome coronavirus.

Journal: Journal of medicinal chemistry 20070823

Title: Triterpenoids from the floral spikes of Betula platyphylla var. japonica and their reversing activity against multidrug-resistant cancer cells.

Journal: Journal of natural products 20070401

Title: Triterpenoid pyrazines and benzopyrazines with cytotoxic activity.

Journal: Journal of natural products 20070401

Title: Biotransformation of betulinic and betulonic acids by fungi.

Journal: Phytochemistry 20070301

Title: A new benzofuranone and anti-HIV constituents from the stems of Rhus chinensis.

Journal: Planta medica 20070301

Title: Boc-lysinated-betulonic acid: a potent, anti-prostate cancer agent.

Journal: Bioorganic & medicinal chemistry 20060915

Title: Cytotoxic terpenes and lignans from the roots of Ainsliaea acerifolia.

Journal: Archives of pharmacal research 20060301

Title: Effect of betulonic acid and its derivative [3-oxo-20(29)-lupene-28-oyl]-3-aminopropionic acid on liver structure in mice with RLS lymphoma.

Journal: Bulletin of experimental biology and medicine 20050901

Title: [Qualitative and quantitative methods of betulonic acid in fruits of Liquidambar formosana].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20050801

Title: Betulinic acid and its derivatives, potent DNA topoisomerase II inhibitors, from the bark of Bischofia javanica.

Journal: Chemistry & biodiversity 20050501

Title: [Synthesis and antitumor activity of cyclopropane derivatives of betulinic and betulonic acids].

Journal: Bioorganicheskaia khimiia 20050101

Title: [The effect of betulonic acid and its alanine amide derivatives on rat liver parenchyma repair during postcytostatic period].

Journal: Eksperimental'naia i klinicheskaia farmakologiia 20050101

Title: Synthesis and cytotoxic activity of 3-O-acyl/3-hydrazine /2-bromo/20,29-dibromo betulinic acid derivatives.

Journal: Bioorganic & medicinal chemistry letters 20040802

Title: Synthesis of A-seco derivatives of betulinic acid with cytotoxic activity.

Journal: Journal of natural products 20040701

Title: Synthesis of 3-O-acyl/3-benzylidene/3-hydrazone/3-hydrazine/17-carboxyacryloyl ester derivatives of betulinic acid as anti-angiogenic agents.

Journal: Bioorganic & medicinal chemistry letters 20040621

Title: Betulinic acid and its derivatives as anti-angiogenic agents.

Journal: Bioorganic & medicinal chemistry letters 20040503

Title: [Synthesis and antiviral activity of amides and conjugates of betulonic acid with amino acids].

Journal: Bioorganicheskaia khimiia 20040101

Title: Betulonic acid and derivatives, a new group of agents reducing side effects of cytostatics.

Journal: Doklady biological sciences : proceedings of the Academy of Sciences of the USSR, Biological sciences sections 20040101

Title: Lupane triterpenes and derivatives with antiviral activity.

Journal: Bioorganic & medicinal chemistry letters 20031020

Title: Antiviral activity of betulin, betulinic and betulonic acids against some enveloped and non-enveloped viruses.

Journal: Fitoterapia 20030701

Title: Natural anti-HIV agents. Part IV. Anti-HIV constituents from Vatica cinerea.

Journal: Journal of natural products 20030201

Title: [Intermolecular interactions of dipeptide triterpene derivatives and natural quinones with alpha-tocopherol].

Journal: Biomeditsinskaia khimiia 20030101

Title: [Studies on chemical constituents in fruit of Eucalyptus globulus].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20020801

Title: Microbial transformations of two lupane-type triterpenes and anti-tumor-promoting effects of the transformation products.

Journal: Journal of natural products 20020301

Title: Selective cytotoxicity of betulinic acid on tumor cell lines, but not on normal cells.

Journal: Cancer letters 20020110

Title: Anti-AIDS agents. 48.(1) Anti-HIV activity of moronic acid derivatives and the new melliferone-related triterpenoid isolated from Brazilian propolis.

Journal: Journal of natural products 20011001

Title: Development of C-20 modified betulinic acid derivatives as antitumor agents.

Journal: Bioorganic & medicinal chemistry letters 20010903

Title: Anti-herpes simplex virus activity of moronic acid purified from Rhus javanica in vitro and in vivo.

Journal: The Journal of pharmacology and experimental therapeutics 19990401

Title: Anti-AIDS agents--XXVII. Synthesis and anti-HIV activity of betulinic acid and dihydrobetulinic acid derivatives.

Journal: Bioorganic & medicinal chemistry 19971201

Title: Bastos DZL, et, al. Biotransformation of betulinic and betulonic acids by fungi. Phytochemistry. 2007 Mar;68(6):834-9.

Title: Yang SJ, et, al. Synthesis and biological evaluation of betulonic acid derivatives as antitumor agents. Eur J Med Chem. 2015;96:58-65.

Title: Sá MS, et, al. Antimalarial activity of betulinic acid and derivatives in vitro against Plasmodium falciparum and in vivo in P. berghei-infected mice. Parasitol Res. 2009 Jul;105(1):275-9.

Title: Pavlova NI, et, al. Antiviral activity of betulin, betulinic and betulonic acids against some enveloped and non-enveloped viruses. Fitoterapia. 2003 Jul;74(5):489-92.

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