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Record Information
Version3.6
Creation Date2006-08-13 09:18:02 UTC
Update Date2017-09-21 20:53:26 UTC
HMDB IDHMDB0004026
Secondary Accession Numbers
  • HMDB04026
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
ValueSource
(3beta)-3,21-Dihydroxypregn-5-en-20-oneChEBI
(3b)-3,21-Dihydroxypregn-5-en-20-oneGenerator
(3β)-3,21-dihydroxypregn-5-en-20-oneGenerator
(3b)-3,21-Dihydroxy-pregn-5-en-20-oneHMDB
3b,21-Dihydroxy-5-pregnen-20-oneHMDB
3b,21-Dihydroxy-pregn-5-en-20-oneHMDB
5-Pregnen-3.beta.,21-diol-20-oneHMDB
5-Pregnen-3b,21-diol-20-oneHMDB
5-Pregnen-3beta,21-diol-20-oneHMDB
Oprea1_642453HMDB
Pregn-5-ene-3b,21-diol-20-oneHMDB
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[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]ethan-1-one
Traditional 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
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
  • 20-oxosteroid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Oxosteroid
  • Delta-5-steroid
  • Alpha-hydroxy ketone
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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 mg/mLALOGPS
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 Area57.53 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity95.46 m3·mol-1ChemAxon
Polarizability38.84 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-004u-4910000000-a498e59adb4a11849d3eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - GC-MSsplash10-004u-4910000000-a498e59adb4a11849d3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
11-beta-hydroxylase deficiency (CYP11B1)Pw000551Pw000551 greyscalePw000551 simpleNot Available
17-alpha-hydroxylase deficiency (CYP17)Pw000542Pw000542 greyscalePw000542 simpleNot Available
21-hydroxylase deficiency (CYP21)Pw000552Pw000552 greyscalePw000552 simpleNot Available
3-Beta-Hydroxysteroid Dehydrogenase DeficiencyPw000695Pw000695 greyscalePw000695 simpleNot Available
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase DeficiencyPw000177Pw000177 greyscalePw000177 simpleNot Available
Displaying entries 1 - 5 of 11 in total
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    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 LinkHMDB0004026
    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