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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:00 UTC
HMDB IDHMDB0000315
Secondary Accession Numbers
  • HMDB00315
Metabolite Identification
Common Name16-a-Hydroxypregnenolone
Description16-alpha-hydroxypregnenolone, also known as 16A OH-Preg or (3beta,16alpha)-3,16-dihydroxypregn-5-en-20-one, is classified as a gluco/mineralocorticoid, a progestogin or aprogestogin derivative. Gluco/mineralocorticoids are steroids with a structure based on a hydroxylated prostane moiety. Thus, 16-alpha-hydroxypregnenolone is a steroid or more correctly a 16alpha-hydroxy steroid. 16-alpha-hydroxypregnenolone is also classified as a hydroxypregnenolone. A hydroxypregnenolone is a pregnenolone substituted by an alpha-hydroxy group at position 16. It is a steroid molecule that is produced by all vertebrates. In humans, 16-alpha-hydroxypregnenolone can be found primarily in blood, urine and in human umbilical cord tissue. 16-alpha-Hydroxypregnenolone is a normal urinary metabolite with increased total excretion in newborn infants with congenital adrenal hyperplasia due to 21-hydroxylase deficiency (PMID 6980322 ). It is therefore an important urinary marker for the occurrence of an adrenal 21-hydroxylase-deficiency. Its levels are an indication for the effectiveness of medication (cortisol supplement) against this disease. (PMID: 10399855 ).
Structure
Thumb
Synonyms
Chemical FormulaC21H32O3
Average Molecular Weight332.477
Monoisotopic Molecular Weight332.23514489
IUPAC Name1-[(1S,2R,5S,10S,11S,13R,14R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one
Traditional Name1-[(1S,2R,5S,10S,11S,13R,14R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethanone
CAS Registry Number520-88-7
SMILES
[H][C@@]12C[C@@H](O)[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C21H32O3/c1-12(22)19-18(24)11-17-15-5-4-13-10-14(23)6-8-20(13,2)16(15)7-9-21(17,19)3/h4,14-19,23-24H,5-11H2,1-3H3/t14-,15+,16-,17-,18+,19-,20-,21-/m0/s1
InChI KeyZAKJZPQDUPCXSD-YRWKUUEZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 20-oxosteroid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 16-hydroxysteroid
  • 16-alpha-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Umbilical cord
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified16.1 +/- 2.3 uMNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified0.05 (0.0 - 0.1) umol/mmol creatinineNewborn (0-30 days old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Not Available
Congenital adrenal hyperplasia
details
Associated Disorders and Diseases
Disease References
Congenital Adrenal Hyperplasia, due to 21-Hydroxylase-Deficiency
  1. Homoki J, Teller WM: Increased urinary excretion of total 16 alpha-hydroxypregnenolone in newborn infants with congenital adrenal hyperplasia due to 21-hydroxylase deficiency. Klin Wochenschr. 1982 Apr 15;60(8):407-10. [PubMed:6980322 ]
Associated OMIM IDs
  • 201910 (Congenital Adrenal Hyperplasia, due to 21-Hydroxylase-Deficiency)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021942
KNApSAcK IDNot Available
Chemspider ID4955002
KEGG Compound IDC06390
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5304
PubChem Compound6452574
PDB IDNot Available
ChEBI ID771
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferencePierrepoint, C. G.; Griffiths, Keith; Grant, James K. In vitro studies of feminizing tumors of the testis of man and dog. Proc. Int. Congr. Horm. Steroids, 2nd (1967), Meeting Date 1966, 761-6.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lee SH, Nam SY, Chung BC: Altered profile of endogenous steroids in the urine of patients with prolactinoma. Clin Biochem. 1998 Oct;31(7):529-35. [PubMed:9812172 ]
  2. Homoki J, Teller WM: Increased urinary excretion of total 16 alpha-hydroxypregnenolone in newborn infants with congenital adrenal hyperplasia due to 21-hydroxylase deficiency. Klin Wochenschr. 1982 Apr 15;60(8):407-10. [PubMed:6980322 ]
  3. Wolthers BG, Kraan GP: Clinical applications of gas chromatography and gas chromatography-mass spectrometry of steroids. J Chromatogr A. 1999 May 28;843(1-2):247-74. doi: 10.1016/s0021-9673(99)00153-3. [PubMed:10399855 ]