Record Information
Version1.0
Creation date2010-04-08 22:14:06 UTC
Update date2019-11-26 03:17:01 UTC
Primary IDFDB019040
Secondary Accession Numbers
  • FDB019041
  • FDB019042
Chemical Information
FooDB Name(2alpha,3alpha,5alpha,22R,23R)-2,3,22,23-Tetrahydroxy-25-methylergost-24(28)en-6-one
Description(2alpha,3alpha,5alpha,22R,23R)-2,3,22,23-Tetrahydroxy-25-methylergost-24(28)en-6-one, also known as 25-methyldiolichosterone, belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups (2alpha,3alpha,5alpha,22R,23R)-2,3,22,23-Tetrahydroxy-25-methylergost-24(28)en-6-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number111618-87-2
Structure
Thumb
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.024 g/LALOGPS
logP3.05ALOGPS
logP3.53ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)13.3ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity133.4 m³·mol⁻¹ChemAxon
Polarizability55.53 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC29H48O5
IUPAC name14-(3,4-dihydroxy-6,6-dimethyl-5-methylideneheptan-2-yl)-4,5-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-8-one
InChI IdentifierInChI=1S/C29H48O5/c1-15(25(33)26(34)16(2)27(3,4)5)18-8-9-19-17-12-22(30)21-13-23(31)24(32)14-29(21,7)20(17)10-11-28(18,19)6/h15,17-21,23-26,31-34H,2,8-14H2,1,3-7H3
InChI KeyHAOQPQZVDMAOKT-UHFFFAOYSA-N
Isomeric SMILESCC(C(O)C(O)C(=C)C(C)(C)C)C1CCC2C3CC(=O)C4CC(O)C(O)CC4(C)C3CCC12C
Average Molecular Weight476.6884
Monoisotopic Molecular Weight476.350174646
Classification
Description Belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTetrahydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Ergosterol-skeleton
  • Ergostane-skeleton
  • Tetrahydroxy bile acid, alcohol, or derivatives
  • Ecdysteroid
  • 23-hydroxysteroid
  • 22-hydroxysteroid
  • 3-hydroxysteroid
  • 2-hydroxysteroid
  • Hydroxysteroid
  • Oxosteroid
  • 6-oxosteroid
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Route of exposure:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 73.07%; H 10.15%; O 16.78%DFC
Melting PointMp 254° (246-247°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]22D +4.3 (c, 0.13 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(2alpha,3alpha,5alpha,22R,23R)-2,3,22,23-Tetrahydroxy-25-methylergost-24(28)en-6-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-1507900000-897e16ccbea7ecb07da8Spectrum
Predicted GC-MS(2alpha,3alpha,5alpha,22R,23R)-2,3,22,23-Tetrahydroxy-25-methylergost-24(28)en-6-one, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-2210029000-30690aab9742d3c68536Spectrum
Predicted GC-MS(2alpha,3alpha,5alpha,22R,23R)-2,3,22,23-Tetrahydroxy-25-methylergost-24(28)en-6-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06vi-0102900000-2fd81e8b2a091a1036052015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-4908600000-5884bd376a7478af53882015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-4903000000-6cf175c82182fbb9e7b82015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0001900000-60025f5dbcc3fecbecba2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9208700000-89a36f122832868194d92015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9104000000-b96e458fdd73a33458122015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06ur-1019400000-6c5a3de93160cfe404252021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07w9-1019100000-104c888a3346d41060022021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9501000000-950dac189be4f90068b82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0001900000-86a4f613459c2b1bffae2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-1105900000-992b4544e6eac49e2a842021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0009400000-ad283d56f2ffd21611a12021-09-23View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDLNR69-J:LNR70-D
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00000194
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.