Human Metabolome Database Version 3.5

Showing metabocard for 11b-Hydroxyprogesterone (HMDB04031)

Record Information
Version 3.5
Creation Date 2006-08-13 03:23:58 -0600
Update Date 2013-05-29 13:39:23 -0600
HMDB ID HMDB04031
Secondary Accession Numbers
  • HMDB13594
Metabolite Identification
Common Name 11b-Hydroxyprogesterone
Description 11beta-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 Link_out) 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 Link_out, 2537337 Link_out). 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 Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (11beta)-11-hydroxypregn-4-ene-3,20-dione
  2. 11-beta-Hydroxypregn-4-ene-3,20-dione
  3. 11-beta-Hydroxyprogesterone
  4. 11b-Hydroxyprogesterone
  5. 11beta-hydroxypregn-4-ene-3,20-dione
  6. 11beta-Hydroxyprogesterone
  7. 21-Deoxycorticosterone
Chemical Formula C20H28O4
Average Molecular Weight 332.4339
Monoisotopic Molecular Weight 332.198759384
IUPAC Name (1S,2R,10S,11S,14S,15S,17R)-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-14-carboxylic acid
Traditional IUPAC Name 11β-hydroxyprogesterone
CAS Registry Number 600-57-7
SMILES [H][C@@]12CC[C@H](C(O)=O)[C@@]1(C)C[C@@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier InChI=1S/C20H28O4/c1-19-8-7-12(21)9-11(19)3-4-13-14-5-6-15(18(23)24)20(14,2)10-16(22)17(13)19/h9,13-17,22H,3-8,10H2,1-2H3,(H,23,24)/t13-,14-,15+,16+,17+,19-,20-/m0/s1
InChI Key XEFVQCSDIKHROY-CAPFDLLWSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Gluco/mineralocorticoids, Progestogins and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives(Lipidmaps)
Substituents
  • 11 Hydroxy Steroid
  • 3 Keto Steroid
  • Carboxylic Acid
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Decaline
  • Ketone
  • Secondary Alcohol
Direct Parent Gluco/mineralocorticoids, Progestogins and Derivatives
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.064 g/L ALOGPS
LogP 1.97 ALOGPS
LogP 2.51 ChemAxon
LogS -3.71 ALOGPS
pKa (strongest acidic) 4.68 ChemAxon
pKa (strongest basic) -0.26 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 74.6 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 90.75 ChemAxon
Polarizability 36.77 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Muscle
  • Skeletal Muscle
  • Bladder
  • Fibroblasts
  • Intestine
  • Neuron
  • Placenta
  • Testes
  • Kidney
  • Epidermis
  • Thyroid Gland
  • Myelin
  • Prostate
  • Adrenal Gland
  • Adipose Tissue
  • Adrenal Cortex
  • Nerve Cells
  • Platelet
  • Gonads
  • Spleen
Pathways
Name SMPDB Link KEGG Link
Steroidogenesis SMP00130 map00140 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.00002 +/- 0.00001 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023284
KNApSAcK ID Not Available
Chemspider ID 24840621 Link_out
KEGG Compound ID C05498 Link_out
BioCyc ID CPD-272 Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB04031 Link_out
Metagene Link HMDB04031 Link_out
METLIN ID 7005 Link_out
PubChem Compound 44263342 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Rosenkranz, 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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  7. Wiebe JP: Nongenomic actions of steroids on gonadotropin release. Recent Prog Horm Res. 1997;52:71-99; discussion 99-101. Pubmed: 9238848 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  17. Tuckey RC: Progesterone synthesis by the human placenta. Placenta. 2005 Apr;26(4):273-81. Pubmed: 15823613 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out

Enzymes
Name: Cytochrome P450 11B1, mitochondrial
Reactions:
Progesterone + Reduced ferredoxin + Oxygen unknown 11b-Hydroxyprogesterone + Oxidized ferredoxin + Water details
Gene Name: CYP11B1
Uniprot ID: P15538 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Steroid 17-alpha-hydroxylase/17,20 lyase
Reactions:
21-Deoxycortisol + Acceptor + Water unknown 11b-Hydroxyprogesterone + Reduced acceptor + Oxygen details
Gene Name: CYP17A1
Uniprot ID: P05093 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 11B2, mitochondrial
Reactions:
Progesterone + Reduced ferredoxin + Oxygen unknown 11b-Hydroxyprogesterone + Oxidized ferredoxin + Water details
Gene Name: CYP11B2
Uniprot ID: P19099 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450, family 21, subfamily A, polypeptide 2
Reactions: Not Available
Gene Name: CYP21A2
Uniprot ID: Q08AG9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Steroid 21-hydroxylase
Reactions:
11b-Hydroxyprogesterone + Reduced acceptor + Oxygen unknown Corticosterone + Acceptor + Water details
Gene Name: CYP21A2
Uniprot ID: P08686 Link_out
Protein Sequence: FASTA