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Record Information
Version3.6
Creation Date2006-08-13 09:18:02 UTC
Update Date2013-05-29 19:39:21 UTC
HMDB IDHMDB04026
Secondary Accession NumbersNone
Metabolite Identification
Common Name21-Hydroxypregnenolone
Description21-hydroxypregnenolone is an essential intermediate in corticosterone synthesis. The hydrolysis of 21-hydroxypregnenolone of fetal origin by steryl-sulfatase (SOS, EC 3.1.6.2), may be important in the biosynthesis of deoxycorticosterone, which is present in the plasma of pregnant women in high concentration. 21-hydroxypregnenolone has been identified in follicular fluid from follicles of women. Pregnenolone is transformed to 21-hydroxypregnenolone by human adrenal microsomal preparations, suggesting the involvement of alternative paths via 17a,21-dihydroxypregnenolone in human. (PMID 974176 , 3347051 , 3495701 , 7382480 , 6247575 ).
Structure
Thumb
Synonyms
  1. (3b)-3,21-dihydroxy-Pregn-5-en-20-one
  2. 21-Hydroxypregnenolone
  3. 3b,21-Dihydroxy-5-pregnen-20-one
  4. 3b,21-Dihydroxy-Pregn-5-en-20-one
  5. 5-Pregnen-3.beta.,21-diol-20-one
  6. 5-Pregnen-3b,21-diol-20-one
  7. 5-Pregnen-3beta,21-diol-20-one
  8. Oprea1_642453
  9. Pregn-5-ene-3b,21-diol-20-one
Chemical FormulaC21H32O3
Average Molecular Weight332.477
Monoisotopic Molecular Weight332.23514489
IUPAC Name2-hydroxy-1-[(1S,2R,5S,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one
Traditional IUPAC Name21-hydroxypregnenolone
CAS Registry Number1164-98-3
SMILES
[H][C@@]12CC[C@H](C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C21H32O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h3,14-18,22-23H,4-12H2,1-2H3/t14-,15-,16-,17-,18+,20-,21-/m0/s1
InChI KeyMOIQRAOBRXUWGN-WPWXJNKXSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassGluco/mineralocorticoids, Progestogins and Derivatives
Other Descriptors
  • 21-hydroxy steroid(ChEBI)
  • 3beta-hydroxy steroid(ChEBI)
  • Aliphatic Homopolycyclic Compounds
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives(Lipidmaps)
  • hydroxypregnenolone(ChEBI)
Substituents
  • 20 Keto Steroid
  • 3 Hydroxy Steroid
  • Alpha Ketoaldehyde
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Ketone
  • Primary Alcohol
  • Secondary Alcohol
Direct ParentGluco/mineralocorticoids, Progestogins and Derivatives
Ontology
StatusDetected and 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 (predicted from logP)
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 solubility0.045 g/LALOGPS
logP3.22ALOGPS
logP2.76ChemAxon
logS-3.9ALOGPS
pKa (strongest acidic)13.86ChemAxon
pKa (strongest basic)-1.4ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count2ChemAxon
polar surface area57.53ChemAxon
rotatable bond count2ChemAxon
refractivity95.46ChemAxon
polarizability38.84ChemAxon
Spectra
SpectraGC-MS
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
SteroidogenesisSMP00130map00140
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
UrineDetected and Quantified2.9 +/- 0.8 umol/mmol creatinineNewborn (0-30 days old)Not SpecifiedNormal details
UrineDetected and Quantified0.04 +/- 0.02 umol/mmol creatinineAdult (>18 years old)BothNormal details
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 IDFDB023281
KNApSAcK IDNot Available
Chemspider ID216208
KEGG Compound IDC05485
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04026
Metagene LinkHMDB04026
METLIN ID7002
PubChem Compound247020
PDB IDNot Available
ChEBI ID28043
References
Synthesis ReferenceDaniewski, Andrzej Robert; Wojciechowska, Wanda. Preparation of 5-pregnene-3b, 21-diol-20-one. Pol. (1987), 4 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kaufmann SH, Sinterhauf K, Lommer D: Alternative pathways in human corticosteroid biosynthesis. J Steroid Biochem. 1980 Jun;13(6):599-605. Pubmed: 6247575
  2. Iudaev NA, Afinogenova SA: [Pathways of corticosteroid biosynthesis in human adrenals (Itsenko-Cushing disease)] Biokhimiia. 1976 Sep;41(9):1619-27. Pubmed: 974176
  3. Shackleton CH, Homoki J, Taylor NF: A paradox: elevated 21-hydroxypregnenolone production in newborns with 21-hydroxylase deficiency. Steroids. 1987 Apr-May;49(4-5):295-311. Pubmed: 3502660
  4. Guerami A, Varner MW, Shackleton CH, MacDonald PC, Casey ML: Origin of deoxycorticosterone and deoxycorticosterone sulfate in human pregnancy: absence of steroid 21-sulfatase activity in sulfatase-deficient placenta. J Steroid Biochem. 1988 Jan;29(1):57-62. Pubmed: 3347051
  5. Dehennin L, Nahoul K, Scholler R: Steroid 21-hydroxylation by human preovulatory follicles from stimulated cycles: a mass spectrometrical study of deoxycorticosterone, 21-hydroxypregnenolone and 11-deoxycortisol in follicular fluid. J Steroid Biochem. 1987 Mar;26(3):337-43. Pubmed: 3495701
  6. Kaufmann SH, Sinterhauf K, Lommer D: 21-Hydroxylation of pregnenolone by microsomal preparations of rat and human adrenals. J Steroid Biochem. 1980 Jan;13(1):101-3. Pubmed: 7382480

Enzymes

General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. Efficiently catalyzes the transformation of pregnenolone to progesterone, 17-alpha-hydroxypregnenolone to 17-alpha-hydroxyprogesterone, DHEA to 4-androstenedione, dihydrotestosterone to 5-alpha-androstane-3 beta,17 beta-diol, dehydroepiandrosterone to androstenedione and 5-alpha-androstan-3 beta,17 beta-diol to 5-alpha-dihydrotestosterone.
Gene Name:
HSD3B1
Uniprot ID:
P14060
Molecular weight:
42251.25
Reactions
21-Hydroxypregnenolone + NAD → Deoxycorticosterone + NADH + Hydrogen Iondetails
General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids.
Gene Name:
HSD3B2
Uniprot ID:
P26439
Molecular weight:
42051.845
Reactions
21-Hydroxypregnenolone + NAD → Deoxycorticosterone + NADH + Hydrogen Iondetails
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
P450-CYP21B
Uniprot ID:
Q16874
Molecular weight:
56000.9
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP21A2
Uniprot ID:
Q08AG9
Molecular weight:
55972.9
General function:
Not Available
Specific function:
Specifically catalyzes the 21-hydroxylation of steroids. Required for the adrenal synthesis of mineralocorticoids and glucocorticoids.
Gene Name:
CYP21A2
Uniprot ID:
P08686
Molecular weight:
56000.94
Reactions
Pregnenolone + Reduced acceptor + Oxygen → 21-Hydroxypregnenolone + Acceptor + Waterdetails