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Showing Compound beta-Amyrin (FDB004092)

Record Information
Version1.0
Creation date2010-04-08 22:06:05 UTC
Update date2025-11-18 22:55:09 UTC
Primary IDFDB004092
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namebeta-Amyrin
DescriptionBeta-amyrin, also known as amyrin or (3beta)-olean-12-en-3-ol, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Thus, beta-amyrin is considered to be an isoprenoid lipid molecule. Beta-amyrin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Beta-amyrin can be synthesized from oleanane. Beta-amyrin is also a parent compound for other transformation products, including but not limited to, erythrodiol, glycyrrhetaldehyde, and 24-hydroxy-beta-amyrin. Beta-amyrin can be found in a number of food items such as thistle, pepper (c. baccatum), wakame, and endive, which makes beta-amyrin a potential biomarker for the consumption of these food products. The amyrins are three closely related natural chemical compounds of the triterpene class. They are designated α-amyrin (ursane skeleton), β-amyrin (oleanane skeleton) and δ-amyrin. Each is a pentacyclic triterpenol with the chemical formula C30H50O. They are widely distributed in nature and have been isolated from a variety of plant sources such as epicuticular wax. In plant biosynthesis, α-amyrin is the precursor of ursolic acid and β-amyrin is the precursor of oleanolic acid. All three amyrins occur in the surface wax of tomato fruit. α-Amyrin is found in dandelion coffee .
CAS Number559-70-6
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(3beta)-Olean-12-en-3-olChEBI
3beta-Hydroxyolean-12-eneChEBI
AmyrinChEBI
beta-AmyrenolChEBI
(3b)-Olean-12-en-3-olGenerator
(3Β)-olean-12-en-3-olGenerator
3b-Hydroxyolean-12-eneGenerator
3Β-hydroxyolean-12-eneGenerator
b-AmyrenolGenerator
Β-amyrenolGenerator
b-AmyrinGenerator
Β-amyrinGenerator
alpha-AmyrinMeSH
Amyrin, (3alpha)-isomerMeSH
Olean-12-en-3beta-olPhytoBank
Olean-12-en-3β-olPhytoBank
(+)-beta-AmyrinPhytoBank
(+)-β-AmyrinPhytoBank
beta-AmirinPhytoBank
β-AmirinPhytoBank
beta-AmyrinPhytoBank
beta-AmyrinePhytoBank
β-AmyrinePhytoBank
β-amirinebiospider
β-amyrenolbiospider
β-amyrinbiospider
Beta-amyrenolbiospider
Beta.-amyrenolbiospider
Beta.-amyrinbiospider
Olean-12-en-3-olbiospider
Olean-12-en-3-ol, (3β)-biospider
Olean-12-en-3-ol, (3beta)- (9CI)biospider
Olean-12-en-3β-olbiospider
Predicted Properties
PropertyValueSource
Water Solubility7.2e-05 g/LALOGPS
logP7.53ALOGPS
logP7.4ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)19.49ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity131.91 m³·mol⁻¹ChemAxon
Polarizability53.86 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC30H50O
IUPAC name(3S,4aR,6aR,6bS,8aR,12aR,14aR,14bR)-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-ol
InChI IdentifierInChI=1S/C30H50O/c1-25(2)15-16-27(5)17-18-29(7)20(21(27)19-25)9-10-23-28(6)13-12-24(31)26(3,4)22(28)11-14-30(23,29)8/h9,21-24,31H,10-19H2,1-8H3/t21-,22-,23+,24-,27+,28-,29+,30+/m0/s1
InChI KeyJFSHUTJDVKUMTJ-QHPUVITPSA-N
Isomeric SMILESCC1(C)CC[C@]2(C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2C1
Average Molecular Weight426.7174
Monoisotopic Molecular Weight426.386166222
Classification
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
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point197 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0010900000-ba7658250bf46d7eb5982016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-1677900000-3786eb5b3042cc1ffa652016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w2j-1779100000-01f35dc4ed9f513499b22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-36d280fb50f37e8d4f652016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-65a47f003658adb277f82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-1019500000-b5ca2bf136a77442f7e82016-08-03View Spectrum
NMRNot Available
ChemSpider ID65921
ChEMBL IDCHEMBL455098
KEGG Compound IDC08616
Pubchem Compound ID73145
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDBETA-AMYRIN
BIGG IDNot Available
KNApSAcK IDC00003738
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Analgesic35480 An agent that relieves pain by reducing or blocking pain signals in the brain, commonly used to manage acute or chronic pain, inflammation, and fever, with therapeutic applications in surgery, injury, and disease treatment.DUKE
Anti-edemicAn agent that relieves or prevents edema, reducing abnormal fluid accumulation in tissues or the circulatory system, commonly used to treat conditions such as swelling, inflammation, and water retention.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti nociceptive35470 An agent that reduces the sensitivity to painful stimuli, blocking the transmission of pain signals. Its biological role is to modulate pain perception, with therapeutic applications in managing acute and chronic pain. Key medical uses include treating headaches, arthritis, and post-surgical pain, as well as providing relief for cancer and neuropathic pain.DUKE
Anti ulcer49201 An agent that reduces stomach acid and protects the mucous lining, preventing ulcer formation. It is used to treat conditions like gastroesophageal reflux disease (GERD), peptic ulcers, and Zollinger-Ellison syndrome, promoting healing and relieving symptoms.DUKE
Gastroprotective55324 An agent that protects the stomach and intestinal lining, reducing inflammation and preventing damage. It has therapeutic applications in managing gastrointestinal disorders, such as ulcers and gastritis, and is commonly used to prevent NSAID-induced stomach damage and treat acid reflux disease.DUKE
Hepatoprotective62868 An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities.DUKE
LarvicideAn insecticide that targets the larval life stage of insects, preventing their development into adults. Its biological role is to control insect populations, and its therapeutic applications include managing mosquito-borne diseases such as malaria and dengue fever, as well as controlling pest infestations in agriculture and public health.DUKE
Mosquitocide24852 An agent that kills mosquitoes, playing a crucial role in preventing the spread of mosquito-borne diseases. Therapeutically, it is used to control insect vectors, reducing the risk of diseases like malaria, dengue fever, and Zika virus. Key medical uses include public health campaigns and epidemic control measures.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.