(2xi,20beta)-2,20-Dihydroxy-3-oxo-12-ursen-28-oic acid (CHEM030313)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:48:50 UTC
Update Date2016-11-09 01:19:03 UTC
Accession NumberCHEM030313
Identification
Common Name(2xi,20beta)-2,20-Dihydroxy-3-oxo-12-ursen-28-oic acid
ClassSmall Molecule
Description(2xi,20beta)-2,20-Dihydroxy-3-oxo-12-ursen-28-oic acid is found in pomes. (2xi,20beta)-2,20-Dihydroxy-3-oxo-12-ursen-28-oic acid is a constituent of apple skin.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2XI,20b)-2,20-dihydroxy-3-oxo-12-ursen-28-OateGenerator
(2XI,20b)-2,20-dihydroxy-3-oxo-12-ursen-28-Oic acidGenerator
(2XI,20beta)-2,20-dihydroxy-3-oxo-12-ursen-28-OateGenerator
(2XI,20β)-2,20-dihydroxy-3-oxo-12-ursen-28-OateGenerator
(2XI,20β)-2,20-dihydroxy-3-oxo-12-ursen-28-Oic acidGenerator
(1R,2S,4AR,6as,6BR,12ar,14BS)-2,11-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylateHMDB
Chemical FormulaC30H46O5
Average Molecular Mass486.683 g/mol
Monoisotopic Mass486.335 g/mol
CAS Registry NumberNot Available
IUPAC Name(1R,2S,4aR,6aS,6bR,12aR,14bS)-2,11-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-10-oxo-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 Name(1R,2S,4aR,6aS,6bR,12aR,14bS)-2,11-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,7,8,8a,11,12,12b,13,14b-dodecahydro-1H-picene-4a-carboxylic acid
SMILES[H][C@@]12[C@@H](C)[C@@](C)(O)CC[C@@]1(CC[C@]1(C)C2=CCC2[C@@]3(C)CC(O)C(=O)C(C)(C)C3CC[C@@]12C)C(O)=O
InChI IdentifierInChI=1S/C30H46O5/c1-17-22-18-8-9-21-26(4)16-19(31)23(32)25(2,3)20(26)10-11-28(21,6)27(18,5)12-14-30(22,24(33)34)15-13-29(17,7)35/h8,17,19-22,31,35H,9-16H2,1-7H3,(H,33,34)/t17-,19?,20?,21?,22+,26+,27-,28-,29+,30-/m1/s1
InChI KeyUYHSBQDAYWOYNS-LDQQKAIHSA-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
  • Tertiary alcohol
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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 Solubility0.0033 g/LALOGPS
logP5.1ALOGPS
logP4.96ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)4.64ChemAxon
pKa (Strongest Basic)-0.68ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity136.05 m³·mol⁻¹ChemAxon
Polarizability55.79 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0600-1001900000-9ce2cfd9562098d36aa6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-014i-1000129000-1225613f8c8f2f1fd5c0Spectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0000900000-bdd9de1495aa9e456fdbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gi0-0011900000-2bcf5c4bae250fa045a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0479800000-8a533014455653a8d354Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-5ca1a967de8a92fc48f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00rl-0000900000-add1d7c4cbab094c1367Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ou-1002900000-a45267d4a648ccfcf9b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-6a75a140e72d68a6c193Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000900000-47ca96216497c9cb9830Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00y0-0000900000-15654a2f6c1de5aefccfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000900000-8f81521a4c60e1897174Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-2005900000-40c8bdb8aac6a105f573Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-100r-1639200000-b1d0de77d2bd2ae863e3Spectrum
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 IDHMDB0036652
FooDB IDFDB015578
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35014178
ChEBI ID168713
PubChem Compound ID131752022
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM