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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:34:43 UTC
Update Date2020-05-01 17:33:53 UTC
HMDB IDHMDB0030094
Secondary Accession Numbers
  • HMDB30094
Metabolite Identification
Common NameBetulinic acid
DescriptionBetulinic acid is found in abiyuch. Betulinic acid is a naturally occurring pentacyclic triterpenoid which has anti-retroviral, anti-malarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase. It is found in the bark of several species of plants, principally the white birch (Betula pubescens) from which it gets its name, but also the Ber tree (Ziziphus mauritiana), the tropical carnivorous plants Triphyophyllum peltatum and Ancistrocladus heyneanus, Diospyros leucomelas a member of the persimmon family, Tetracera boiviniana, the jambul (Syzygium formosanum), flowering quince (Chaenomeles sinensis), Rosemary, and Pulsatilla chinensis. Controversial is a role of p53 in betulinic acid-induced apoptosis. Fulda suggested p53-independent mechanism of the apoptosis, basing on fact of no accumulation of wild-type p53 detected upon treatment with the betulinic acid, whereas wild-type p53 protein strongly increased after treatment with doxorubicin. The suggestion is supported by study of Raisova. On the other hand Rieber suggested that betulinic acid exerts its inhibitory effect on human metastatic melanoma partly by increasing p53
Structure
Data?1588354433
Synonyms
ValueSource
MairinChEBI
BetulinateGenerator
3-Epi-betulinic acidHMDB
Betulic acidHMDB
Chemical FormulaC30H48O3
Average Molecular Weight456.711
Monoisotopic Molecular Weight456.360345406
IUPAC Name(1R,2R,5S,8R,9R,10R,13R,14R,17S,19R)-17-hydroxy-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-5-carboxylic acid
Traditional Name(1R,2R,5S,8R,9R,10R,13R,14R,17S,19R)-17-hydroxy-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-5-carboxylic acid
CAS Registry Number472-15-1
SMILES
[H][C@]12[C@@H](CC[C@@]1(CC[C@]1(C)[C@]2([H])CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O)C(C)=C
InChI Identifier
InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1
InChI KeyQGJZLNKBHJESQX-FZFNOLFKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • 18-oxosteroid
  • 18-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Carbonyl group
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point316 - 318 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0002 g/LALOGPS
logP5.34ALOGPS
logP6.64ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)4.75ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity132.63 m³·mol⁻¹ChemAxon
Polarizability54.64 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0019400000-d634f687c0b20b3bf518Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0019400000-946b3acbf03ebc325984Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-06vi-0009700000-133d884e7fe1aabfb659Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-06vr-0019800000-a2c226a96551460f31b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0000411190-9e794d71d8e215a3ef7fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0000511290-00b42fd32f4bea1aac24Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004i-0009100000-02c4ffe35137e2459ef9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004i-0009100000-b369b92782bf0058f776Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0000900000-31877b3328749253f478Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0000900000-46226c91dca257ecbdbeSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004i-0119300000-d165dda7f84c911bb084Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004i-0119400000-c8efa7eb386af139bbbbSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0000900000-5daf110b6535ef5e1cbaSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0000900000-1a6ea554c157db014b7cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-01p9-0000900000-95cc62b5cf4bd28b6108Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-01p9-0000900000-1a328cc168bc37caf6d7Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4r-0920300000-e3035523b40f714793c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0001900000-b8dd0421a0b0886464d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01vy-0007900000-fa6391d5931c416add2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0016-3359300000-9f556d5f0a61208b8cdeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-5567c27847c37f89e74fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fu-0003900000-4699eedd9cf8bfc1aa61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000e-2007900000-4109b9ad459c3012d1abSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12480
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00003741
Chemspider ID58496
KEGG Compound IDC08619
BioCyc IDCPD-14493
BiGG IDNot Available
Wikipedia LinkBetulinic_acid
METLIN IDNot Available
PubChem Compound64971
PDB IDNot Available
ChEBI ID3087
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Rzeski W, Stepulak A, Szymanski M, Sifringer M, Kaczor J, Wejksza K, Zdzisinska B, Kandefer-Szerszen M: Betulinic acid decreases expression of bcl-2 and cyclin D1, inhibits proliferation, migration and induces apoptosis in cancer cells. Naunyn Schmiedebergs Arch Pharmacol. 2006 Oct;374(1):11-20. Epub 2006 Sep 9. [PubMed:16964520 ]
  2. Lo YC, Chang YH, Wei BL, Huang YL, Chiou WF: Betulinic acid stimulates the differentiation and mineralization of osteoblastic MC3T3-E1 cells: involvement of BMP/Runx2 and beta-catenin signals. J Agric Food Chem. 2010 Jun 9;58(11):6643-9. doi: 10.1021/jf904158k. [PubMed:20443623 ]
  3. Mukherjee R, Jaggi M, Rajendran P, Srivastava SK, Siddiqui MJ, Vardhan A, Burman AC: Synthesis of 3-O-acyl/3-benzylidene/3-hydrazone/3-hydrazine/17-carboxyacryloyl ester derivatives of betulinic acid as anti-angiogenic agents. Bioorg Med Chem Lett. 2004 Jun 21;14(12):3169-72. [PubMed:15149668 ]
  4. Viji V, Shobha B, Kavitha SK, Ratheesh M, Kripa K, Helen A: Betulinic acid isolated from Bacopa monniera (L.) Wettst suppresses lipopolysaccharide stimulated interleukin-6 production through modulation of nuclear factor-kappaB in peripheral blood mononuclear cells. Int Immunopharmacol. 2010 Aug;10(8):843-9. doi: 10.1016/j.intimp.2010.04.013. Epub 2010 Apr 26. [PubMed:20430119 ]
  5. Liu WK, Ho JC, Cheung FW, Liu BP, Ye WC, Che CT: Apoptotic activity of betulinic acid derivatives on murine melanoma B16 cell line. Eur J Pharmacol. 2004 Sep 13;498(1-3):71-8. [PubMed:15363977 ]
  6. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  7. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  8. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  9. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  10. (). Afendi FM, Okada T, Yamazaki M, Hirai-Morita A, Nakamura Y, Nakamura K, Ikeda S, Takahashi H, Altaf-Ul-Amin M, Darusman LK, Saito K, Kanaya S. (2012) KNApSAcK family databases: integrated metabolite-plant species databases for multifaceted plant research. Plant Cell Physiol. 2012 Feb;53(2):e1.. .
  11. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.