Maslinic acid (CHEM028567)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:32:36 UTC
Update Date2016-11-09 01:18:43 UTC
Accession NumberCHEM028567
Identification
Common NameMaslinic acid
ClassSmall Molecule
DescriptionA pentacyclic triterpenoid that is olean-12-ene substituted by hydroxy groups at positions 2 and 3 and a carboxy group at position 28 (the 2alpha,3beta stereoisomer). It is isolated from Olea europaea and Salvia canariensis and exhibits anti-inflammatory, antioxidant and antineoplastic activity.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Crategolic acidChEBI
Masilinic acidChEBI
CrategolateGenerator
MasilinateGenerator
MaslinateGenerator
(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
(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
Bredemolic acidHMDB
Maslic acidHMDB
Chemical FormulaC30H48O4
Average Molecular Mass472.700 g/mol
Monoisotopic Mass472.355 g/mol
CAS Registry Number4373-41-5
IUPAC Name(4aS,6aS,6bR,8aR,10R,11R,12aR,12bR,14bS)-10,11-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
Traditional Namemaslinic acid
SMILESCC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(C)C5CCC34C)C2C1)C(O)=O
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
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
  • Cyclic alcohol
  • Secondary alcohol
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Polarizability55.78 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0023900000-ad901ef5c32d3c8515c9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-1000029000-b4246244219ca8eb0227Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0udi-0791000000-84517830fd9e957962caSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0002-0900000000-c233f2a131f72e107d2fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0000900000-387883ee881aa4b13f53Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0341900000-f9db1dc7e767773bc516Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0c00-0641900000-2c004cf7e547633d868cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0010900000-48dd9d7b2670fb1d9915Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-05mk-0900000000-998f0309b3ae3acecb35Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0udi-0980100000-53fdc3bf88a89370c2b6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-05tb-1900000000-81eb8d8d7f4e5bc19689Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-05tb-1900000000-6fa3337ddc72a4000985Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0zfr-0490000000-78d39a8a0e7a33b0b5dcSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0pb9-0690800000-2df4abcc46063a3a59f9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0010900000-099025ecae557ce6de7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0000900000-a3caade25e22f29c6b48Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a70-0111900000-ca10b86ddab0b1c39223Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2586900000-46428c996e2cb58156adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-a6b6ada0368b6de45648Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05di-0000900000-37088e9ac327fedc6f6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-0000900000-e4ebefda17c04ba388caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-ce83f241675374237da4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0000900000-df2b3ea552ae00b11362Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0000900000-ca6d9ef7df5c2201c99eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000900000-23194a03010761625bc5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05g1-1085900000-17b4120f33e31f9f06f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0941000000-2da99d319567a1e7f60eSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002392
FooDB IDFDB013041
Phenol Explorer IDNot Available
KNApSAcK IDC00030742
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMaslinic_acid
Chemspider ID66312
ChEBI ID66682
PubChem Compound ID73659
Kegg Compound IDC16939
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12802735
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21288041
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21309591
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21384845
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21973054
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23003682
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23175023
8. Wen, Xiaoan; Zhang, Pu; Liu, Jun; Zhang, Luyong; Wu, Xiaoming; Ni, Peizhou; Sun, Hongbin. Pentacyclic triterpenes. Part 2: Synthesis and biological evaluation of maslinic acid derivatives as glycogen phosphorylase inhibitors. Bioorg Med Chem Lett. 2006 Feb;16(3):722-6. Epub 2005 Oct 21. Pubmed: 16246555
9. Marquez-Martin A, De La Puerta R, Fernandez-Arche A, Ruiz-Gutierrez V, Yaqoob P: Modulation of cytokine secretion by pentacyclic triterpenes from olive pomace oil in human mononuclear cells. Cytokine. 2006 Dec;36(5-6):211-7. Epub 2007 Feb 9.