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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:36 UTC
HMDB IDHMDB00382
Secondary Accession NumbersNone
Metabolite Identification
Common Name3b,17a,21-Trihydroxypregnenone
Description3b,17a,21-Trihydroxypregnenone is an intermediate in the human fetus at midpregnancy converting it to cortisol (PMID 4231965 ). It has been found as an intermediate in alternative pathways in human adrenal steroidogenesis that take place under in vitro conditions of normal adrenal slices from patients with hypernephroid kidney carcinomas that bypass cholesterol, pregnenolone, progesterone and proceed to 21-hydroxypregnenolone (PMID 6247575 ).
Structure
Thumb
Synonyms
ValueSource
17,21-DihydroxypregnenoloneHMDB
17a,21-DihydroxypregnenoloneHMDB
3b,17a,21-Trihydroxypregn-5-en-20-oneHMDB
Chemical FormulaC21H32O4
Average Molecular Weight348.4764
Monoisotopic Molecular Weight348.230059512
IUPAC Name(1S,2S,10S,11S,14S,15S)-5,14-dihydroxy-14-(2-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-3-one
Traditional Name(1S,2S,10S,11S,14S,15S)-5,14-dihydroxy-14-(2-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-3-one
CAS Registry Number1167-48-2
SMILES
[H][C@@]12CC[C@](O)(CCO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C
InChI Identifier
InChI=1S/C21H32O4/c1-19-7-5-17-15(16(19)6-8-21(19,25)9-10-22)4-3-13-11-14(23)12-18(24)20(13,17)2/h12-13,15-17,22-23,25H,3-11H2,1-2H3/t13?,15-,16-,17-,19-,20-,21-/m0/s1
InChI KeyInChIKey=RJKJQHWLCLYSHD-DGFNXGTDSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • 21-hydroxysteroid
  • Progestogin-skeleton
  • Pregnane-skeleton
  • 17-hydroxysteroid
  • Oxosteroid
  • 1-oxosteroid
  • 3-hydroxysteroid
  • Vinylogous acid
  • Tertiary alcohol
  • Cyclic alcohol
  • Ketone
  • Enol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.055 mg/mLALOGPS
logP2.33ALOGPS
logP2.39ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)8.84ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity97.84 m3·mol-1ChemAxon
Polarizability40.01 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022000
KNApSAcK IDNot Available
Chemspider ID17215943
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00382
Metagene LinkHMDB00382
METLIN ID5371
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceHeer, J.; Miescher, K. Steroids. CIV. The synthesis of the dihydroxyacetone side chain in the steroid series. Helvetica Chimica Acta (1951), 34 359-72.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pasqualini JR, Lowy J, Wiqvist N, Diczfalusy E: Biosynthesis of cortisol from 3 beta, 17 alpha,21-trihydroxypregn-5-en-20-one by the intact human foetus at midpregnancy. Biochim Biophys Acta. 1968 May 1;152(3):648-50. [4231965 ]
  2. Kaufmann SH, Sinterhauf K, Lommer D: Alternative pathways in human corticosteroid biosynthesis. J Steroid Biochem. 1980 Jun;13(6):599-605. [6247575 ]