You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 09:23:58 UTC
Update Date2020-08-13 16:56:01 UTC
HMDB IDHMDB0004031
Secondary Accession Numbers
  • HMDB0013594
  • HMDB04031
  • HMDB13594
Metabolite Identification
Common Name11beta-Hydroxyprogesterone
Description11beta-Hydroxyprogesterone is a normal human metabolite. Plasma 11beta-Hydroxyprogesterone concentrations does not vary significantly as a function of age, sex, or phase of the menstrual cycle, in contrast to 17-hydroxyprogesterone. Increased plasma 11beta-Hydroxyprogesterone levels in late-onset adrenal 21-hydroxylase deficiency suggest a mild defect of the mineralocorticoid pathway. 21-hydroxylase deficiency (OMIM 201910 ) is probably the most frequent (if not the most frequent) autosomal recessive genetic disease, occurring in almost 1% of Caucasians and about 3% of Ashkenazi Jews. 21-hydroxylase deficiency is unusual among genetic diseases in that approximately 95% of the mutant alleles have apparently been generated by recombination between a normally active gene (CYP21) and a closely linked pseudogene (CYP21P). There are 4 recognized clinical forms of congenital adrenal hyperplasia, the majority of cases being associated with 21-hydroxylase deficiency: salt-wasting (SW), simple virilizing (SV), nonclassic (NC) late-onset (also called attenuated and acquired), and cryptic. (PMID: 3546944 , 2537337 ). 11beta-hydroxyprogesterone acts as a mineralocorticoid agonist in stimulating Na+ absorption in mammalian principal cortical collecting duct cells.It activates the transiently expressed hMR in COS-7 cells in a dose-dependent manner (ED(50): 10(-8) M) and, like aldosterone, stimulated Ams I(sc) in mpkCCD(cl4) cells. Docking 11OHP within the hMR-ligand-binding domain homology model revealed that the agonist activity of 11OHP is caused by contacts between its 11 beta-hydroxyl group and Asn770. Furthermore, 11OHP was unable to activate the mutant hMR/N770A, in which Ala is substituted for Asn at position 770. These findings demonstrate that in the absence of the 21-hydroxyl group, the 11 beta-hydroxyl group can produce the contact with the hMR-Asn770 required for the hMR activation leading to stimulated Na(+) absorption.
Structure
Data?1597337575
Synonyms
ValueSource
(11beta)-11-Hydroxypregn-4-ene-3,20-dioneChEBI
21-DeoxycorticosteroneChEBI
(11b)-11-Hydroxypregn-4-ene-3,20-dioneGenerator
(11Β)-11-hydroxypregn-4-ene-3,20-dioneGenerator
11b-HydroxyprogesteroneGenerator
11Β-hydroxyprogesteroneGenerator
Pregn-4-ene-11 beta-ol-3,20-dioneMeSH
HylutinMeSH
HyprogestMeSH
11-Hydroxyprogesterone, (11alpha,17alpha)-(+-)-isomerMeSH
11-HydroxyprogesteroneMeSH
DuralutinMeSH
ProdroxMeSH
11 beta-Hydroxy-4-pregnen-3,20-dioneMeSH
11-Hydroxyprogesterone, (11beta)-isomerMeSH
11-Hydroxyprogesterone, (11alpha)-(+-)-isomerMeSH
11-Hydroxyprogesterone, (9beta,10alpha,11alpha)-isomerMeSH
11 alpha-HydroxyprogesteroneMeSH
11ohp CompoundMeSH
Hy-gestroneMeSH
PergestronMeSH
Pro-depoMeSH
GesterolMeSH
11-Hydroxyprogesterone, (11alpha)-isomerMeSH
11beta-Hydroxy-4-pregnene-3,20-dioneHMDB
11beta-Hydroxy-P4HMDB
11beta-HydroxyprogesteroneHMDB
11β-Hydroxy-4-pregnene-3,20-dioneHMDB
11β-Hydroxy-P4HMDB
Pregn-4-en-11beta-ol-3,20-dioneHMDB
Pregn-4-en-11β-ol-3,20-dioneHMDB
Pregn-4-ene-11beta-ol-3,20-dioneHMDB
Pregn-4-ene-11β-ol-3,20-dioneHMDB
delta4-Pregnene-11beta-ol-3,20-dioneHMDB
Δ4-Pregnene-11β-ol-3,20-dioneHMDB
Chemical FormulaC21H30O3
Average Molecular Weight330.4611
Monoisotopic Molecular Weight330.219494826
IUPAC Name(1S,2R,10S,11S,14S,15S,17S)-14-acetyl-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional Name(1S,2R,10S,11S,14S,15S,17S)-14-acetyl-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
CAS Registry Number600-57-7
SMILES
[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C21H30O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h10,15-19,24H,4-9,11H2,1-3H3/t15-,16+,17-,18-,19+,20-,21+/m0/s1
InChI KeyBFZHCUBIASXHPK-ATWVFEABSA-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-oxo-delta-4-steroid
  • 3-oxosteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Hydroxysteroid
  • Oxosteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

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 Solubility0.064 g/LALOGPS
logP2.65ALOGPS
logP2.84ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)18.88ChemAxon
pKa (Strongest Basic)-0.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity94.3 m³·mol⁻¹ChemAxon
Polarizability38.12 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 MEOX; 1 TMS)splash10-0ffx-4910000000-0cca73076134866f5851Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 MEOX; 1 TMS)splash10-0ffx-4900000000-22180c23fc90db83965bSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue Locations
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Bladder
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Neuron
  • Ovary
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
  • Testis
  • Thyroid Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00002 +/- 0.00001 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023284
KNApSAcK IDNot Available
Chemspider ID91968
KEGG Compound IDC05498
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link11β-Hydroxyprogesterone
METLIN IDNot Available
PubChem Compound101788
PDB IDNot Available
ChEBI ID28247
Food Biomarker OntologyNot Available
VMH IDM00285
MarkerDB ID
References
Synthesis ReferenceRosenkranz, G.; Pataki, J.; Djerassi, Carl. Steroids. XXIX. Synthesis of 11b-hydroxyprogesterone. Journal of Organic Chemistry (1952), 17 290-3.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lambert JJ, Belelli D, Peden DR, Vardy AW, Peters JA: Neurosteroid modulation of GABAA receptors. Prog Neurobiol. 2003 Sep;71(1):67-80. [PubMed:14611869 ]
  2. Herrero P, Soto PF, Dence CS, Kisrieva-Ware Z, Delano DA, Peterson LR, Gropler RJ: Impact of hormone replacement on myocardial fatty acid metabolism: potential role of estrogen. J Nucl Cardiol. 2005 Sep-Oct;12(5):574-81. [PubMed:16171718 ]
  3. Antic T, Perry KT, Harrison K, Zaytsev P, Pins M, Campbell SC, Picken MM: Mixed epithelial and stromal tumor of the kidney and cystic nephroma share overlapping features: reappraisal of 15 lesions. Arch Pathol Lab Med. 2006 Jan;130(1):80-5. [PubMed:16390243 ]
  4. Shikone T, Matzuk MM, Perlas E, Finegold MJ, Lewis KA, Vale W, Bradley A, Hsueh AJ: Characterization of gonadal sex cord-stromal tumor cell lines from inhibin-alpha and p53-deficient mice: the role of activin as an autocrine growth factor. Mol Endocrinol. 1994 Aug;8(8):983-95. [PubMed:7997239 ]
  5. Barnhill SD, Zhang Z, Madyastha KR: Evaluation of a new biochemical index for the estimation of bone demineralization using artificial intelligence. Contemp Orthop. 1995 Apr;30(4):315-8. [PubMed:10150355 ]
  6. Saxena BB, Clavio A, Singh M, Rathnam P, Bukharovich EY, Reimers TJ Jr, Saxena A, Perkins S: Effect of immunization with bovine luteinizing hormone receptor on ovarian function in cats. Am J Vet Res. 2003 Mar;64(3):292-8. [PubMed:12661868 ]
  7. Wiebe JP: Nongenomic actions of steroids on gonadotropin release. Recent Prog Horm Res. 1997;52:71-99; discussion 99-101. [PubMed:9238848 ]
  8. Holtta-Vuori M, Maatta J, Ullrich O, Kuismanen E, Ikonen E: Mobilization of late-endosomal cholesterol is inhibited by Rab guanine nucleotide dissociation inhibitor. Curr Biol. 2000 Jan 27;10(2):95-8. [PubMed:10662671 ]
  9. Celayir S, Ilce Z, Dervisoglu S: The sex hormone receptors in the bladder in childhood - I: preliminary report in male subjects. Eur J Pediatr Surg. 2002 Oct;12(5):312-7. [PubMed:12469257 ]
  10. Agoulnik IU, Krause WC, Bingman WE 3rd, Rahman HT, Amrikachi M, Ayala GE, Weigel NL: Repressors of androgen and progesterone receptor action. J Biol Chem. 2003 Aug 15;278(33):31136-48. Epub 2003 May 27. [PubMed:12771131 ]
  11. Laatikainen T, Apter D, Wahlstrom T: Steroids in spermatic and peripheral vein blood in testicular feminization. Fertil Steril. 1980 Nov;34(5):461-4. [PubMed:7439411 ]
  12. Beer R, Barnhill SD, Madyastha KR: Comparative study of a biochemical index for the estimation of bone demineralization and dual photon absorptiometry. Contemp Orthop. 1995 Mar;30(3):230-4. [PubMed:10150317 ]
  13. Pepe GJ, Albrecht ED: Actions of placental and fetal adrenal steroid hormones in primate pregnancy. Endocr Rev. 1995 Oct;16(5):608-48. [PubMed:8529574 ]
  14. Feuring M, Christ M, Roell A, Schueller P, Losel R, Dempfle CE, Schultz A, Wehling M: Alterations in platelet function during the ovarian cycle. Blood Coagul Fibrinolysis. 2002 Jul;13(5):443-7. [PubMed:12138372 ]
  15. Rasmussen KM, Kjolhede CL: Prepregnant overweight and obesity diminish the prolactin response to suckling in the first week postpartum. Pediatrics. 2004 May;113(5):e465-71. [PubMed:15121990 ]
  16. Parikh P, Chan TY, Epstein JI, Argani P: Incidental stromal-predominant mixed epithelial-stromal tumors of the kidney: a mimic of intraparenchymal renal leiomyoma. Arch Pathol Lab Med. 2005 Jul;129(7):910-4. [PubMed:15974815 ]
  17. Tuckey RC: Progesterone synthesis by the human placenta. Placenta. 2005 Apr;26(4):273-81. [PubMed:15823613 ]
  18. Money SR, Muss W, Thelmo WL, Boeckl O, Pimpl W, Kaindl H, Sungler P, Kirwin J, Waclawicek H, Jaffe BM, et al.: Immunocytochemical localization of estrogen and progesterone receptors in human thyroid. Surgery. 1989 Dec;106(6):975-8; discussion 979. [PubMed:2686061 ]
  19. Karalis K, Goodwin G, Majzoub JA: Cortisol blockade of progesterone: a possible molecular mechanism involved in the initiation of human labor. Nat Med. 1996 May;2(5):556-60. [PubMed:8616715 ]
  20. Sereda MW, Meyer zu Horste G, Suter U, Uzma N, Nave KA: Therapeutic administration of progesterone antagonist in a model of Charcot-Marie-Tooth disease (CMT-1A). Nat Med. 2003 Dec;9(12):1533-7. Epub 2003 Nov 9. [PubMed:14608378 ]
  21. Gueux B, Fiet J, Galons H, Bonete R, Villette JM, Vexiau P, Pham-Huu-Trung MT, Raux-Eurin MC, Gourmelen M, Brerault JL, et al.: The measurement of 11 beta-hydroxy-4-pregnene-3,20-dione (21-deoxycorticosterone) by radioimmunoassay in human plasma. J Steroid Biochem. 1987 Jan;26(1):145-50. [PubMed:3546944 ]
  22. Fiet J, Gueux B, Raux-DeMay MC, Kuttenn F, Vexiau P, Brerault JL, Couillin P, Galons H, Villette JM, Julien R, et al.: Increased plasma 21-deoxycorticosterone (21-DB) levels in late-onset adrenal 21-hydroxylase deficiency suggest a mild defect of the mineralocorticoid pathway. J Clin Endocrinol Metab. 1989 Mar;68(3):542-7. [PubMed:2537337 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochrome P450 XIB.
Gene Name:
CYP11B1
Uniprot ID:
P15538
Molecular weight:
57572.44
Reactions
Progesterone + Reduced ferredoxin + Oxygen → 11beta-Hydroxyprogesterone + Oxidized ferredoxin + Waterdetails
General function:
Involved in monooxygenase activity
Specific function:
Conversion of pregnenolone and progesterone to their 17-alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation and the 17,20-lyase reaction. Involved in sexual development during fetal life and at puberty.
Gene Name:
CYP17A1
Uniprot ID:
P05093
Molecular weight:
57369.995
Reactions
21-Deoxycortisol + Acceptor + Water → 11beta-Hydroxyprogesterone + Reduced acceptor + Oxygendetails
General function:
Involved in monooxygenase activity
Specific function:
Preferentially catalyzes the conversion of 11-deoxycorticosterone to aldosterone via corticosterone and 18-hydroxycorticosterone.
Gene Name:
CYP11B2
Uniprot ID:
P19099
Molecular weight:
57559.62
Reactions
Progesterone + Reduced ferredoxin + Oxygen → 11beta-Hydroxyprogesterone + Oxidized ferredoxin + Waterdetails
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
11beta-Hydroxyprogesterone + Reduced acceptor + Oxygen → Corticosterone + Acceptor + Waterdetails