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Bredemolic acid

PubChem CID: 3694932

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Compound Synonyms bredemolic acid, 26563-68-8, 2,3-dihydroxyolean-12-en-28-oic acid, 2,3-Dihydroxy-12-oleanen-28-oic acid, 5957-40-4, SCHEMBL23716504, DTXSID70863386, BBA56368, STL564445, AKOS037623082, LS-15296, NS00018298, B0005-177401, (4aS,6aR,6aS,6bR,12aR,14bR)-10,11-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Topological Polar Surface Area 77.8
Hydrogen Bond Donor Count 3.0
Heavy Atom Count 34.0
Description Maslinic 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)
Isotope Atom Count 0.0
Molecular Complexity 919.0
Database Name cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;npass_chem_all;pubchem
Defined Atom Stereocenter Count 0.0
Iupac Name 10,11-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Prediction Hob 0.0
Class Prenol lipids
Xlogp 6.5
Superclass Lipids and lipid-like molecules
Subclass Triterpenoids
Molecular Formula C30H48O4
Prediction Swissadme 0.0
Inchi Key MDZKJHQSJHYOHJ-UHFFFAOYSA-N
Fcsp3 0.9
Rotatable Bond Count 1.0
State Solid
Synonyms (2.alpha.,3.beta.)-2,3-dihydroxy-olean-12-en-28-Oate, (2.alpha.,3.beta.)-2,3-dihydroxy-olean-12-en-28-Oic acid, (2alpha,3beta)- 2,3-Dihydroxy-olean-12-en-28-Oate, (2alpha,3beta)- 2,3-Dihydroxy-olean-12-en-28-Oic acid, (2alpha,3beta)-2,3-Dihydroxy-olean-12-en-28-oate, (2alpha,3beta)-2,3-Dihydroxy-olean-12-en-28-oic acid, (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 acid, Crataegolic acid, Crategolate, Crategolic acid, Masilinate, Masilinic acid, Maslinic acid, Maslinate
Substituent Name 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
Compound Name Bredemolic acid
Kingdom Organic compounds
Prediction Hob Swissadme 0.0
Exact Mass 472.355
Formal Charge 0.0
Monoisotopic Mass 472.355
Hydrogen Bond Acceptor Count 4.0
Molecular Weight 472.7
Covalent Unit Count 1.0
Total Atom Stereocenter Count 9.0
Total Bond Stereocenter Count 0.0
Molecular Framework Aliphatic homopolycyclic compounds
Esol -6.806102000000002
Inchi 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)
Smiles CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CC(C(C5(C)C)O)O)C)C)C2C1)C)C(=O)O)C
Defined Bond Stereocenter Count 0.0
Taxonomy Direct Parent Triterpenoids