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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:10:51 UTC
Update Date2022-03-07 02:56:40 UTC
HMDB IDHMDB0040618
Secondary Accession Numbers
  • HMDB40618
Metabolite Identification
Common Name16-Hydroxy-3-oxo-12-oleanen-28-oic acid
Description16-Hydroxy-3-oxo-12-oleanen-28-oic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Based on a literature review a small amount of articles have been published on 16-Hydroxy-3-oxo-12-oleanen-28-oic acid.
Structure
Data?1563863569
Synonyms
ValueSource
16-Hydroxy-3-oxo-12-oleanen-28-OateGenerator
5-Hydroxy-2,2,6a,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 FormulaC30H46O4
Average Molecular Weight470.6838
Monoisotopic Molecular Weight470.33960996
IUPAC Name5-hydroxy-2,2,6a,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 Name5-hydroxy-2,2,6a,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
CAS Registry Number77625-71-9
SMILES
CC1(C)CCC2(C(O)CC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CCC34C)C2C1)C(O)=O
InChI Identifier
InChI=1S/C30H46O4/c1-25(2)14-15-30(24(33)34)19(16-25)18-8-9-21-27(5)12-11-22(31)26(3,4)20(27)10-13-28(21,6)29(18,7)17-23(30)32/h8,19-21,23,32H,9-17H2,1-7H3,(H,33,34)
InChI KeyNMCMUIZIKSPDCX-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
  • Beta-hydroxy acid
  • Hydroxy acid
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point212 - 214 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0019 g/LALOGPS
logP5.88ALOGPS
logP5.93ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)4.61ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity134.32 m³·mol⁻¹ChemAxon
Polarizability55.18 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+209.41331661259
DarkChem[M-H]-202.59731661259
DeepCCS[M-2H]-248.74630932474
DeepCCS[M+Na]+224.22830932474
AllCCS[M+H]+216.332859911
AllCCS[M+H-H2O]+214.732859911
AllCCS[M+NH4]+217.832859911
AllCCS[M+Na]+218.332859911
AllCCS[M-H]-215.532859911
AllCCS[M+Na-2H]-217.432859911
AllCCS[M+HCOO]-219.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
16-Hydroxy-3-oxo-12-oleanen-28-oic acidCC1(C)CCC2(C(O)CC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CCC34C)C2C1)C(O)=O3107.8Standard polar33892256
16-Hydroxy-3-oxo-12-oleanen-28-oic acidCC1(C)CCC2(C(O)CC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CCC34C)C2C1)C(O)=O3589.9Standard non polar33892256
16-Hydroxy-3-oxo-12-oleanen-28-oic acidCC1(C)CCC2(C(O)CC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CCC34C)C2C1)C(O)=O3913.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
16-Hydroxy-3-oxo-12-oleanen-28-oic acid,1TMS,isomer #1CC1(C)CCC2(C(=O)O)C(O[Si](C)(C)C)CC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CCC43C)C2C13902.8Semi standard non polar33892256
16-Hydroxy-3-oxo-12-oleanen-28-oic acid,1TMS,isomer #2CC1(C)CCC2(C(=O)O[Si](C)(C)C)C(O)CC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CCC43C)C2C13786.5Semi standard non polar33892256
16-Hydroxy-3-oxo-12-oleanen-28-oic acid,1TMS,isomer #3CC1(C)CCC2(C(=O)O)C(O)CC3(C)C(=CCC4C5(C)CC=C(O[Si](C)(C)C)C(C)(C)C5CCC43C)C2C13887.6Semi standard non polar33892256
16-Hydroxy-3-oxo-12-oleanen-28-oic acid,2TMS,isomer #1CC1(C)CCC2(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)CC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CCC43C)C2C13744.1Semi standard non polar33892256
16-Hydroxy-3-oxo-12-oleanen-28-oic acid,2TMS,isomer #2CC1(C)CCC2(C(=O)O)C(O[Si](C)(C)C)CC3(C)C(=CCC4C5(C)CC=C(O[Si](C)(C)C)C(C)(C)C5CCC43C)C2C13802.5Semi standard non polar33892256
16-Hydroxy-3-oxo-12-oleanen-28-oic acid,2TMS,isomer #3CC1(C)CCC2(C(=O)O[Si](C)(C)C)C(O)CC3(C)C(=CCC4C5(C)CC=C(O[Si](C)(C)C)C(C)(C)C5CCC43C)C2C13733.6Semi standard non polar33892256
16-Hydroxy-3-oxo-12-oleanen-28-oic acid,3TMS,isomer #1CC1(C)CCC2(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)CC3(C)C(=CCC4C5(C)CC=C(O[Si](C)(C)C)C(C)(C)C5CCC43C)C2C13689.0Semi standard non polar33892256
16-Hydroxy-3-oxo-12-oleanen-28-oic acid,3TMS,isomer #1CC1(C)CCC2(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)CC3(C)C(=CCC4C5(C)CC=C(O[Si](C)(C)C)C(C)(C)C5CCC43C)C2C13523.3Standard non polar33892256
16-Hydroxy-3-oxo-12-oleanen-28-oic acid,1TBDMS,isomer #1CC1(C)CCC2(C(=O)O)C(O[Si](C)(C)C(C)(C)C)CC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CCC43C)C2C14118.2Semi standard non polar33892256
16-Hydroxy-3-oxo-12-oleanen-28-oic acid,1TBDMS,isomer #2CC1(C)CCC2(C(=O)O[Si](C)(C)C(C)(C)C)C(O)CC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CCC43C)C2C14029.6Semi standard non polar33892256
16-Hydroxy-3-oxo-12-oleanen-28-oic acid,1TBDMS,isomer #3CC1(C)CCC2(C(=O)O)C(O)CC3(C)C(=CCC4C5(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C2C14095.6Semi standard non polar33892256
16-Hydroxy-3-oxo-12-oleanen-28-oic acid,2TBDMS,isomer #1CC1(C)CCC2(C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)CC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CCC43C)C2C14207.8Semi standard non polar33892256
16-Hydroxy-3-oxo-12-oleanen-28-oic acid,2TBDMS,isomer #2CC1(C)CCC2(C(=O)O)C(O[Si](C)(C)C(C)(C)C)CC3(C)C(=CCC4C5(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C2C14225.1Semi standard non polar33892256
16-Hydroxy-3-oxo-12-oleanen-28-oic acid,2TBDMS,isomer #3CC1(C)CCC2(C(=O)O[Si](C)(C)C(C)(C)C)C(O)CC3(C)C(=CCC4C5(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C2C14186.8Semi standard non polar33892256
16-Hydroxy-3-oxo-12-oleanen-28-oic acid,3TBDMS,isomer #1CC1(C)CCC2(C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)CC3(C)C(=CCC4C5(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C2C14333.0Semi standard non polar33892256
16-Hydroxy-3-oxo-12-oleanen-28-oic acid,3TBDMS,isomer #1CC1(C)CCC2(C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)CC3(C)C(=CCC4C5(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C2C14063.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 16-Hydroxy-3-oxo-12-oleanen-28-oic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-06di-1037900000-f883b0ff239238f5a9122017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Hydroxy-3-oxo-12-oleanen-28-oic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0f6t-1011192000-0bf5e2364ed2074112cf2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Hydroxy-3-oxo-12-oleanen-28-oic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Hydroxy-3-oxo-12-oleanen-28-oic acid 10V, Positive-QTOFsplash10-0uk9-0000900000-0a9951e1b1d32f8ddd422017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Hydroxy-3-oxo-12-oleanen-28-oic acid 20V, Positive-QTOFsplash10-0kbr-1001900000-fdb5eb65cf4a1757ab9a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Hydroxy-3-oxo-12-oleanen-28-oic acid 40V, Positive-QTOFsplash10-054k-5129600000-53a16cc7101665e2af482017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Hydroxy-3-oxo-12-oleanen-28-oic acid 10V, Negative-QTOFsplash10-016r-0000900000-bf0878674bc97f7ca69e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Hydroxy-3-oxo-12-oleanen-28-oic acid 20V, Negative-QTOFsplash10-056r-0000900000-a23da825823425cb190e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Hydroxy-3-oxo-12-oleanen-28-oic acid 40V, Negative-QTOFsplash10-0a4i-2001900000-5d20348eb45795700b752017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Hydroxy-3-oxo-12-oleanen-28-oic acid 10V, Negative-QTOFsplash10-014i-0000900000-d60788820b8857f5a5d52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Hydroxy-3-oxo-12-oleanen-28-oic acid 20V, Negative-QTOFsplash10-0690-0000900000-494a8bb5a21f49ccc0d12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Hydroxy-3-oxo-12-oleanen-28-oic acid 40V, Negative-QTOFsplash10-0a4i-0000900000-d95e1379a5175bedde052021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Hydroxy-3-oxo-12-oleanen-28-oic acid 10V, Positive-QTOFsplash10-00di-0000900000-1337051d501eea9eb3442021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Hydroxy-3-oxo-12-oleanen-28-oic acid 20V, Positive-QTOFsplash10-0udi-0409200000-372a12913b36ddb123cf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Hydroxy-3-oxo-12-oleanen-28-oic acid 40V, Positive-QTOFsplash10-052r-2922100000-6fe446bf01905f2058ad2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB020409
KNApSAcK IDNot Available
Chemspider ID35014974
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131752867
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.