| Record Information |
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| Version | 3.6 |
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| Creation Date | 2006-08-13 09:23:58 UTC |
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| Update Date | 2017-03-02 21:27:26 UTC |
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| HMDB ID | HMDB04031 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | 11b-Hydroxyprogesterone |
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| 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 ) 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. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (11beta)-11-Hydroxypregn-4-ene-3,20-dione | HMDB | | 11-beta-Hydroxypregn-4-ene-3,20-dione | HMDB | | 11-beta-Hydroxyprogesterone | HMDB | | 11beta-Hydroxypregn-4-ene-3,20-dione | HMDB | | 11beta-Hydroxyprogesterone | HMDB | | 21-Deoxycorticosterone | HMDB |
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| Chemical Formula | C20H28O4 |
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| Average Molecular Weight | 332.4339 |
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| Monoisotopic Molecular Weight | 332.198759384 |
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| IUPAC Name | (1S,2R,10S,11S,14S,15S,17R)-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-14-carboxylic acid |
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| Traditional Name | 11b-hydroxyprogesterone |
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| CAS Registry Number | 600-57-7 |
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| 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 |
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| 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 |
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| InChI Key | XEFVQCSDIKHROY-CAPFDLLWSA-N |
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| Chemical Taxonomy |
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| Classification | Not classified |
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| Ontology |
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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | - Cell signaling
- Fuel and energy storage
- Fuel or energy source
- Hormones, Membrane component
- Membrane integrity/stability
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| Application | - Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations | - Extracellular
- Membrane (predicted from logP)
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | Not Available |
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- 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 ]
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- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
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