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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:51 UTC
Update Date2021-09-16 15:27:23 UTC
HMDB IDHMDB0002392
Secondary Accession Numbers
  • HMDB02392
Metabolite Identification
Common NameMaslinic acid
DescriptionMaslinic 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 ).
Structure
Data?1582752248
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 Weight472.71
Monoisotopic Molecular Weight472.355260026
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
CAS Registry Number4373-41-5
SMILES
[H][C@@]12CC(C)(C)CC[C@@]1(CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)C[C@@H](O)[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O
InChI Identifier
InChI=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)/t19-,20+,21-,22+,23-,27-,28+,29+,30-/m0/s1
InChI KeyMDZKJHQSJHYOHJ-LLICELPBSA-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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Maslinic acid,1TMS,#13846.6184https://arxiv.org/abs/1905.12712
Maslinic acid,1TMS,#23848.1587https://arxiv.org/abs/1905.12712
Maslinic acid,1TMS,#33768.579https://arxiv.org/abs/1905.12712
Maslinic acid,2TMS,#13735.7307https://arxiv.org/abs/1905.12712
Maslinic acid,2TMS,#23815.832https://arxiv.org/abs/1905.12712
Maslinic acid,2TMS,#33730.6775https://arxiv.org/abs/1905.12712
Maslinic acid,3TMS,#13685.2935https://arxiv.org/abs/1905.12712
Maslinic acid,1TBDMS,#14078.8208https://arxiv.org/abs/1905.12712
Maslinic acid,1TBDMS,#24074.2478https://arxiv.org/abs/1905.12712
Maslinic acid,1TBDMS,#34032.3528https://arxiv.org/abs/1905.12712
Maslinic acid,2TBDMS,#14210.153https://arxiv.org/abs/1905.12712
Maslinic acid,2TBDMS,#24212.836https://arxiv.org/abs/1905.12712
Maslinic acid,2TBDMS,#34191.4795https://arxiv.org/abs/1905.12712
Maslinic acid,3TBDMS,#14297.364https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0023900000-ad901ef5c32d3c8515c92017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-1000029000-b4246244219ca8eb02272017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0udi-0791000000-84517830fd9e957962ca2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0002-0900000000-c233f2a131f72e107d2f2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0000900000-387883ee881aa4b13f532021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0341900000-f9db1dc7e767773bc5162021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0c00-0641900000-2c004cf7e547633d868c2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0010900000-48dd9d7b2670fb1d99152021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-05mk-0900000000-998f0309b3ae3acecb352021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0udi-0980100000-53fdc3bf88a89370c2b62021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-05tb-1900000000-81eb8d8d7f4e5bc196892021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-05tb-1900000000-6fa3337ddc72a40009852021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0zfr-0490000000-78d39a8a0e7a33b0b5dc2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0pb9-0690800000-2df4abcc46063a3a59f92021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0010900000-099025ecae557ce6de7e2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0000900000-a3caade25e22f29c6b482017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a70-0111900000-ca10b86ddab0b1c392232017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2586900000-46428c996e2cb58156ad2017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-a6b6ada0368b6de456482017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05di-0000900000-37088e9ac327fedc6f6d2017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-0000900000-e4ebefda17c04ba388ca2017-06-28View Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013041
KNApSAcK IDC00030742
Chemspider ID66312
KEGG Compound IDC16939
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMaslinic_acid
METLIN IDNot Available
PubChem Compound73659
PDB IDNot Available
ChEBI ID66682
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceWen, 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
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:17292619 ]