Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 03:39:41 UTC
Update Date2021-09-26 22:59:52 UTC
HMDB IDHMDB0249168
Secondary Accession NumbersNone
Metabolite Identification
Common NameBetulonic acid
Description1,2,14,18,18-pentamethyl-17-oxo-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosane-5-carboxylic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 1,2,14,18,18-pentamethyl-17-oxo-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosane-5-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Betulonic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Betulonic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
1,2,14,18,18-Pentamethyl-17-oxo-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0,.0,.0,]henicosane-5-carboxylateGenerator
1,2,14,18,18-Pentamethyl-17-oxo-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosane-5-carboxylateGenerator
BetulonateGenerator
Chemical FormulaC30H46O3
Average Molecular Weight454.695
Monoisotopic Molecular Weight454.344695341
IUPAC Name1,2,14,18,18-pentamethyl-17-oxo-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosane-5-carboxylic acid
Traditional Name1,2,14,18,18-pentamethyl-17-oxo-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosane-5-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC(=C)C1CCC2(CCC3(C)C(CCC4C5(C)CCC(=O)C(C)(C)C5CCC34C)C12)C(O)=O
InChI Identifier
InChI=1S/C30H46O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-22,24H,1,8-17H2,2-7H3,(H,32,33)
InChI KeySLJTWDNVZKIDAU-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
  • 18-oxosteroid
  • 18-hydroxysteroid
  • Hydroxysteroid
  • Oxosteroid
  • Steroid
  • Ketone
  • Cyclic ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP5.81ALOGPS
logP7.2ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)4.75ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity131.8 m³·mol⁻¹ChemAxon
Polarizability53.86 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
DeepCCS[M-2H]-245.47930932474
DeepCCS[M+Na]+220.70830932474
AllCCS[M+H]+213.532859911
AllCCS[M+H-H2O]+211.832859911
AllCCS[M+NH4]+215.132859911
AllCCS[M+Na]+215.532859911
AllCCS[M-H]-214.532859911
AllCCS[M+Na-2H]-216.232859911
AllCCS[M+HCOO]-218.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Betulonic acidCC(=C)C1CCC2(CCC3(C)C(CCC4C5(C)CCC(=O)C(C)(C)C5CCC34C)C12)C(O)=O3064.2Standard polar33892256
Betulonic acidCC(=C)C1CCC2(CCC3(C)C(CCC4C5(C)CCC(=O)C(C)(C)C5CCC34C)C12)C(O)=O3542.7Standard non polar33892256
Betulonic acidCC(=C)C1CCC2(CCC3(C)C(CCC4C5(C)CCC(=O)C(C)(C)C5CCC34C)C12)C(O)=O3702.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Betulonic acid,2TMS,isomer #1C=C(C)C1CCC2(C(=O)O[Si](C)(C)C)CCC3(C)C(CCC4C5(C)CC=C(O[Si](C)(C)C)C(C)(C)C5CCC43C)C123575.0Semi standard non polar33892256
Betulonic acid,2TMS,isomer #1C=C(C)C1CCC2(C(=O)O[Si](C)(C)C)CCC3(C)C(CCC4C5(C)CC=C(O[Si](C)(C)C)C(C)(C)C5CCC43C)C123428.3Standard non polar33892256
Betulonic acid,2TMS,isomer #1C=C(C)C1CCC2(C(=O)O[Si](C)(C)C)CCC3(C)C(CCC4C5(C)CC=C(O[Si](C)(C)C)C(C)(C)C5CCC43C)C123807.2Standard polar33892256
Betulonic acid,2TBDMS,isomer #1C=C(C)C1CCC2(C(=O)O[Si](C)(C)C(C)(C)C)CCC3(C)C(CCC4C5(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C124039.6Semi standard non polar33892256
Betulonic acid,2TBDMS,isomer #1C=C(C)C1CCC2(C(=O)O[Si](C)(C)C(C)(C)C)CCC3(C)C(CCC4C5(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C123810.4Standard non polar33892256
Betulonic acid,2TBDMS,isomer #1C=C(C)C1CCC2(C(=O)O[Si](C)(C)C(C)(C)C)CCC3(C)C(CCC4C5(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)(C)C5CCC43C)C124020.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Betulonic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ug3-1036900000-c2e8c6969cf8174ebd802021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Betulonic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Betulonic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Betulonic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Betulonic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Betulonic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betulonic acid 10V, Positive-QTOFsplash10-0a4i-0002900000-ff433b7ff5975c438d352021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betulonic acid 20V, Positive-QTOFsplash10-052r-0396800000-fd590e3b01786a63e24f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betulonic acid 40V, Positive-QTOFsplash10-0fri-5971000000-9a20f337ea91405db9f22021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betulonic acid 10V, Negative-QTOFsplash10-0udi-0000900000-896a352facf680cb901f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betulonic acid 20V, Negative-QTOFsplash10-0udi-0000900000-896a352facf680cb901f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Betulonic acid 40V, Negative-QTOFsplash10-0udi-0000900000-56985c34cd94aa7ee60d2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound289985
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]