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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-24 10:25:29 UTC
Update Date2021-09-24 10:25:29 UTC
HMDB IDHMDB0304522
Secondary Accession NumbersNone
Metabolite Identification
Common Nametyphasterol
Description2-deoxycastasterone, also known as typhasterol, belongs to trihydroxy bile acids, alcohols and derivatives class of compounds. Those are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. 2-deoxycastasterone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 2-deoxycastasterone can be found in a number of food items such as canola, kumquat, asparagus, and salmonberry, which makes 2-deoxycastasterone a potential biomarker for the consumption of these food products.
Structure
Thumb
Synonyms
ValueSource
TyphasterolHMDB
Chemical FormulaC28H48O4
Average Molecular Weight448.6783
Monoisotopic Molecular Weight448.355260024
IUPAC Name14-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-8-one
Traditional Name14-(3,4-dihydroxy-5,6-dimethylheptan-2-yl)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-8-one
CAS Registry NumberNot Available
SMILES
CC(C)C(C)C(O)C(O)C(C)C1CCC2C3CC(=O)C4CC(O)CCC4(C)C3CCC12C
InChI Identifier
InChI=1S/C28H48O4/c1-15(2)16(3)25(31)26(32)17(4)20-7-8-21-19-14-24(30)23-13-18(29)9-11-28(23,6)22(19)10-12-27(20,21)5/h15-23,25-26,29,31-32H,7-14H2,1-6H3
InChI KeySBSXXCCMIWEPEE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTrihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Ergosterol-skeleton
  • Ergostane-skeleton
  • Ecdysteroid
  • Trihydroxy bile acid, alcohol, or derivatives
  • 23-hydroxysteroid
  • 22-hydroxysteroid
  • 3-hydroxysteroid
  • 6-oxosteroid
  • Oxosteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
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
logP3.73ALOGPS
logP4.58ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)13.64ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity127.86 m³·mol⁻¹ChemAxon
Polarizability54.38 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+212.80432859911
AllCCS[M+H-H2O]+211.01732859911
AllCCS[M+Na]+214.90432859911
AllCCS[M+NH4]+214.43932859911
AllCCS[M-H]-208.95232859911
AllCCS[M+Na-2H]-211.33332859911
AllCCS[M+HCOO]-214.10332859911
DeepCCS[M-2H]-237.44430932474
DeepCCS[M+Na]+212.64630932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
typhasterol,4TMS,isomer #1CC(C)C(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)C1CCC2C3CC(O[Si](C)(C)C)=C4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C3515.1Semi standard non polar33892256
typhasterol,4TMS,isomer #1CC(C)C(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)C1CCC2C3CC(O[Si](C)(C)C)=C4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C3638.1Standard non polar33892256
typhasterol,4TMS,isomer #1CC(C)C(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)C1CCC2C3CC(O[Si](C)(C)C)=C4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C3715.4Standard polar33892256
typhasterol,4TMS,isomer #2CC(C)C(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)C1CCC2C3C=C(O[Si](C)(C)C)C4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C3513.3Semi standard non polar33892256
typhasterol,4TMS,isomer #2CC(C)C(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)C1CCC2C3C=C(O[Si](C)(C)C)C4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C3509.5Standard non polar33892256
typhasterol,4TMS,isomer #2CC(C)C(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C(C)C1CCC2C3C=C(O[Si](C)(C)C)C4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C3687.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - typhasterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-6335900000-d2dc37e1eb8c161fb7162017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - typhasterol GC-MS (3 TMS) - 70eV, Positivesplash10-0f6w-3221139000-dab271e3e801501450bd2017-10-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - typhasterol 10V, Positive-QTOFsplash10-001j-0011900000-e6c796eb955de79ad1a32015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - typhasterol 20V, Positive-QTOFsplash10-0h61-8329500000-24d91d4156e0a4add1ea2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - typhasterol 40V, Positive-QTOFsplash10-0zgi-9434100000-27d6fa255574c0b3eaa22015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - typhasterol 10V, Negative-QTOFsplash10-0002-0001900000-f4cdbf8d4110a62d1ec12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - typhasterol 20V, Negative-QTOFsplash10-0092-5318900000-71c0b4cef0fa9473d8c62015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - typhasterol 40V, Negative-QTOFsplash10-0601-9104100000-2278dba4549530b52f6c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - typhasterol 10V, Positive-QTOFsplash10-001j-0011900000-e6c796eb955de79ad1a32015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - typhasterol 20V, Positive-QTOFsplash10-0h61-8329500000-24d91d4156e0a4add1ea2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - typhasterol 40V, Positive-QTOFsplash10-0zgi-9434100000-27d6fa255574c0b3eaa22015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - typhasterol 10V, Negative-QTOFsplash10-0002-0001900000-f4cdbf8d4110a62d1ec12015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - typhasterol 20V, Negative-QTOFsplash10-0092-5318900000-71c0b4cef0fa9473d8c62015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - typhasterol 40V, Negative-QTOFsplash10-0601-9104100000-2278dba4549530b52f6c2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - typhasterol 10V, Positive-QTOFsplash10-00kb-0056900000-8bc107df472f7a8552072021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - typhasterol 20V, Positive-QTOFsplash10-0gi1-3349100000-adfaec9f2bef953f9ec52021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - typhasterol 40V, Positive-QTOFsplash10-0083-6910000000-c805a44a6659741c9e942021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - typhasterol 10V, Negative-QTOFsplash10-0002-0000900000-48d4ebbdf1be8483b1312021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - typhasterol 20V, Negative-QTOFsplash10-0002-0202900000-cf580d26d64e7504fd0f2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - typhasterol 40V, Negative-QTOFsplash10-066s-3009400000-250a8b4e5998cea7ae032021-10-21Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDFDB012821
KNApSAcK IDC00000186
Chemspider ID21142762
KEGG Compound IDC15793
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13475117
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 ReferencesNot Available