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17alpha,20alpha-Dihydroxycholesterol (FDB024067)

Record Information
Version1.0
Creation date2011-09-21 00:39:21 UTC
Update date2015-07-21 06:57:59 UTC
Primary IDFDB024067
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name17alpha,20alpha-Dihydroxycholesterol
Description17alpha,21-Dihydroxypregnenolone, also known as 3β,17,21-trihydroxy-pregn-5-en-20-one, belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Thus, 17alpha,21-dihydroxypregnenolone is considered to be a steroid lipid molecule. 17alpha,21-Dihydroxypregnenolone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
CAS NumberNot Available
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0054 g/LALOGPS
logP5.05ALOGPS
logP4.87ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)13.25ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity123.6 m³·mol⁻¹ChemAxon
Polarizability50.5 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC27H46O3
IUPAC name(2R,5S,10R,14R,15S)-14-[(2R)-2-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,14-diol
InChI IdentifierInChI=1S/C27H46O3/c1-18(2)7-6-13-26(5,29)27(30)16-12-23-21-9-8-19-17-20(28)10-14-24(19,3)22(21)11-15-25(23,27)4/h8,18,20-23,28-30H,6-7,9-17H2,1-5H3/t20-,21+,22?,23?,24-,25-,26+,27+/m0/s1
InChI KeyPRZXKPDANWDCNC-IMVKCWHASA-N
Isomeric SMILES[H]C12CC[C@](O)([C@](C)(O)CCCC(C)C)[C@@]1(C)CCC1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
Average Molecular Weight418.6523
Monoisotopic Molecular Weight418.344695338
Classification
Description Belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent21-hydroxysteroids
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 21-hydroxysteroid
  • 20-oxosteroid
  • Pregnane-skeleton
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Oxosteroid
  • 3-beta-hydroxy-delta-5-steroid
  • 3-beta-hydroxysteroid
  • 17-hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS17alpha,20alpha-Dihydroxycholesterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0uel-2239400000-41515f4297af4971a848Spectrum
Predicted GC-MS17alpha,20alpha-Dihydroxycholesterol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00xr-2011249000-a657d6ae561e24b74e38Spectrum
Predicted GC-MS17alpha,20alpha-Dihydroxycholesterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS17alpha,20alpha-Dihydroxycholesterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0003900000-f535ba20543aafa8bd7e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fl9-9048500000-57767148817dd16563d32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0avi-9125000000-7949d9d82d4f9d3b20022017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0002900000-95b5f04d6c6ec228cfaf2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014s-2485900000-cd3f9e369ac3a24ebfe12017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0079-1194100000-2d013ecd999936b89e112017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-1115900000-d5e9dc6e8588fe35bcb92021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0901-7931100000-a6fdc1b6f1d0238eb7682021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9720000000-8e7c40e57518c7456eda2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-f2cb6399034352e924c82021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0030900000-99cff478edd24aa7f1632021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07vr-4692300000-68c60377630672ef50502021-09-24View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC05499
Pubchem Compound ID53477898
Pubchem Substance IDNot Available
ChEBI ID783
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06764
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
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
Pathways
NameSMPDB LinkKEGG Link
SteroidogenesisSMP00130 map00140
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference