Record Information
Version1.0
Creation date2010-04-08 22:06:05 UTC
Update date2018-05-28 23:13:22 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
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
β-amirinebiospider
β-amyrenolbiospider
β-amyrinbiospider
Beta-amyrenolbiospider
beta-Amyrinbiospider
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
Olean-12-en-3beta-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
Polarizability53.92 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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 - Experimental
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
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0010900000-ba7658250bf46d7eb598View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-1677900000-3786eb5b3042cc1ffa65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w2j-1779100000-01f35dc4ed9f513499b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-36d280fb50f37e8d4f65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-65a47f003658adb277f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-1019500000-b5ca2bf136a77442f7e8View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
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 capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
anti edemicDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti nociceptive35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
gastroprotective55324 A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion.DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
larvicideDUKE
mosquitocide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.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.