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Showing Compound Maslinic acid (FDB013041)

Record Information
Version1.0
Creation date2010-04-08 22:10:30 UTC
Update date2019-11-26 03:07:54 UTC
Primary IDFDB013041
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMaslinic acid
DescriptionMaslinic acid is a compound derived from dry olive-pomace oil (an olive skin wax) which is a byproduct of olive oil extraction. It is a member of the group of triterpenes known as oleananes.; Maslinic acid is a pentacyclic triterpene, found in the non-glyceride fraction of olive pomace oil (Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption). Pentacyclic triterpenes are natural compounds which are widely distributed in plants. These natural products have been demonstrated to possess anti-inflammatory properties. Triterpenoids have been reported to possess antioxidant properties, since they prevent lipid peroxidation and suppress superoxide anion generation. The triterpenes have a history of medicinal use in many Asian countries. Maslinic acid exhibits both pro- and anti-inflammatory properties depending on chemical structure and dose and may be useful in modulating the immune response; further studies are required to confirm the immunomodulatory behaviour of this triterpenoid, and characterise the mechanisms underlying the biphasic nature of some aspects of the inflammatory response. (PMID: 17292619)
CAS Number4373-41-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(2.alpha.,3.beta.)-2,3-dihydroxy-olean-12-en-28-OateHMDB
(2.alpha.,3.beta.)-2,3-dihydroxy-olean-12-en-28-Oic acidHMDB
(2alpha,3beta)- 2,3-Dihydroxy-olean-12-en-28-OateHMDB
(2alpha,3beta)- 2,3-Dihydroxy-olean-12-en-28-Oic acidHMDB
(2alpha,3beta)-2,3-Dihydroxy-olean-12-en-28-oatebiospider
(2alpha,3beta)-2,3-Dihydroxy-olean-12-en-28-oic acidbiospider
(4AS,6as,6br,8ar,10R,11R,12ar,12br,14bs)-10,11-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2H-picene-4a-carboxylic acidHMDB
Crataegolic acidbiospider
CrategolateGenerator
Crategolic aciddb_source
MasilinateGenerator
Masilinic acidChEBI
Maslinic aciddb_source
Predicted Properties
PropertyValueSource
Water Solubility0.004 g/LALOGPS
logP6.06ALOGPS
logP5.52ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)4.74ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity134.99 m³·mol⁻¹ChemAxon
Polarizability55.72 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC30H48O4
IUPAC name10,11-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid
InChI IdentifierInChI=1S/C30H48O4/c1-25(2)12-14-30(24(33)34)15-13-28(6)18(19(30)16-25)8-9-22-27(5)17-20(31)23(32)26(3,4)21(27)10-11-29(22,28)7/h8,19-23,31-32H,9-17H2,1-7H3,(H,33,34)
InChI KeyMDZKJHQSJHYOHJ-UHFFFAOYSA-N
Isomeric SMILESCC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(C)C5CCC34C)C2C1)C(O)=O
Average Molecular Weight472.6997
Monoisotopic Molecular Weight472.355260024
Classification
DescriptionThis compound belongs to the class of organic compounds known as oleanane triterpenoids. These are triterpenoids with a structure based on the oleanane skeleton, an 4,4,6a,8a,11,14b-heptamethyl-hexadecahydropicene derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentOleanane triterpenoids
Alternative Parents
Substituents
  • Oleanane triterpenoid
  • Cyclic alcohol
  • Secondary alcohol
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Foods

Fats and oils:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 76.23%; H 10.23%; O 13.54%DFC
Melting PointMp 267-269° (243-245°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +42.1 (c, 1.02 in Py)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0023900000-e0267136ecd72810ecd3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0000900000-a3caade25e22f29c6b48JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a70-0111900000-ca10b86ddab0b1c39223JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2586900000-46428c996e2cb58156adJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-a6b6ada0368b6de45648JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05di-0000900000-37088e9ac327fedc6f6dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-0000900000-e4ebefda17c04ba388caJSpectraViewer
ChemSpider ID66312
ChEMBL IDCHEMBL201515
KEGG Compound IDC16939
Pubchem Compound ID73659
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02392
CRC / DFC (Dictionary of Food Compounds) IDHNX65-R:HNX68-U
EAFUS IDNot Available
Dr. Duke IDCRATEGOLIC-ACID|CRATAEGOLIC-ACID|MASLINIC-ACID
BIGG IDNot Available
KNApSAcK IDC00030742
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDMaslinic acid
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
anti edemicDUKE
anti histaminic37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
anti HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
cardiotonic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
digestiveDUKE
protease inhibitor37670 A compound which inhibits or antagonizes the biosynthesis or actions of proteases (endopeptidases).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.