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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:34:43 UTC
Update Date2021-10-13 06:05:34 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
(+)-Betulinic acidPhytoBank
Betulinic acidPhytoBank
Lupatic acidPhytoBank
(3beta)-3-Hydroxylup-20(29)-en-28-oic acidPhytoBank
(3β)-3-Hydroxylup-20(29)-en-28-oic acidPhytoBank
3beta-Hydroxylup-20(29)-en-28-oic acidPhytoBank
3β-Hydroxylup-20(29)-en-28-oic acidPhytoBank
beta-Betulinic acidPhytoBank
β-Betulinic acidPhytoBank
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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point316 - 318 °CNot Available
Boiling Point550.02 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.0016 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP7.653 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0002 g/LALOGPS
logP10(5.34) g/LALOGPS
logP10(6.64) g/LChemAxon
logS10(-6.4) g/LALOGPS
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
Polarizability54.67 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Betulinic acid[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)=C3291.8Standard polar33892256
Betulinic acid[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)=C3599.6Standard non polar33892256
Betulinic acid[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)=C3671.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Betulinic acid,1TMS,isomer #1C=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]123638.4Semi standard non polar33892256
Betulinic acid,1TMS,isomer #2C=C(C)[C@@H]1CC[C@]2(C(=O)O[Si](C)(C)C)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]123537.4Semi standard non polar33892256
Betulinic acid,2TMS,isomer #1C=C(C)[C@@H]1CC[C@]2(C(=O)O[Si](C)(C)C)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]123502.4Semi standard non polar33892256
Betulinic acid,1TBDMS,isomer #1C=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C(C)(C)C)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]123857.7Semi standard non polar33892256
Betulinic acid,1TBDMS,isomer #2C=C(C)[C@@H]1CC[C@]2(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]123799.8Semi standard non polar33892256
Betulinic acid,2TBDMS,isomer #1C=C(C)[C@@H]1CC[C@]2(C(=O)O[Si](C)(C)C(C)(C)C)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O[Si](C)(C)C(C)(C)C)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]123999.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Betulinic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , negative-QTOFsplash10-004i-0019400000-d634f687c0b20b3bf5182017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , negative-QTOFsplash10-004i-0019400000-946b3acbf03ebc3259842017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , negative-QTOFsplash10-06vi-0009700000-133d884e7fe1aabfb6592017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , negative-QTOFsplash10-06vr-0019800000-a2c226a96551460f31b82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , negative-QTOFsplash10-0a4i-0000411190-9e794d71d8e215a3ef7f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , negative-QTOFsplash10-0a4i-0000511290-00b42fd32f4bea1aac242017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , positive-QTOFsplash10-004i-0009100000-02c4ffe35137e2459ef92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , positive-QTOFsplash10-004i-0009100000-b369b92782bf0058f7762017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , positive-QTOFsplash10-0udi-0000900000-31877b3328749253f4782017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , positive-QTOFsplash10-0udi-0000900000-46226c91dca257ecbdbe2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , positive-QTOFsplash10-004i-0119300000-d165dda7f84c911bb0842017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , positive-QTOFsplash10-004i-0119400000-c8efa7eb386af139bbbb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , positive-QTOFsplash10-0udi-0000900000-5daf110b6535ef5e1cba2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , positive-QTOFsplash10-0udi-0000900000-1a6ea554c157db014b7c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , positive-QTOFsplash10-01p9-0000900000-95cc62b5cf4bd28b61082017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betulinic acid Linear Ion Trap , positive-QTOFsplash10-01p9-0000900000-1a328cc168bc37caf6d72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betulinic acid , positive-QTOFsplash10-0a4r-0920300000-e3035523b40f714793c72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betulinic acid 10V, Negative-QTOFsplash10-0a4i-0000900000-d90a9a8ffded459e1b382021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Betulinic acid 20V, Negative-QTOFsplash10-0a4i-0000900000-99c8bb2b318a1cfdacef2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betulinic acid 10V, Positive-QTOFsplash10-052r-0001900000-b8dd0421a0b0886464d32017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betulinic acid 20V, Positive-QTOFsplash10-01vy-0007900000-fa6391d5931c416add2d2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betulinic acid 40V, Positive-QTOFsplash10-0016-3359300000-9f556d5f0a61208b8cde2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betulinic acid 10V, Negative-QTOFsplash10-0a4i-0000900000-5567c27847c37f89e74f2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betulinic acid 20V, Negative-QTOFsplash10-08fu-0003900000-4699eedd9cf8bfc1aa612017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betulinic acid 40V, Negative-QTOFsplash10-000e-2007900000-4109b9ad459c3012d1ab2017-06-28Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents IDrw1223341
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.