| Record Information |
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| Version | 5.0 |
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| Status | Detected and Quantified |
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| Creation Date | 2006-08-13 09:17:15 UTC |
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| Update Date | 2022-09-22 18:34:17 UTC |
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| HMDB ID | HMDB0004025 |
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| Secondary Accession Numbers | - HMDB0005943
- HMDB04025
- HMDB05943
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| Metabolite Identification |
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| Common Name | Pregnanediol |
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| Description | Pregnanediol is an endogenous human testosterone metabolite. It can be detected in the urine of adults and newborns in variable concentrations. Pregnanediol is abnormally elevated in patients with cytochrome P450 (P450C17, steroid 17alpha-monooxygenase, EC 1.14.99.9) oxidoreductase deficiency (Antley-Bixler syndrome, PORD, OMIM: 201750 ). Antley-Bixler syndrome is a multiple congenital malformation syndrome with craniosynostosis, radiohumeral synostosis, femoral bowing, choanal atresia or stenosis, joint contractures, urogenital abnormalities, and often early death. An assay of urinary pregnanediol excretion provides an accurate indication of outcome in threatened miscarriage in 74 - 93% percent of cases. Pregnanediol is one of the most important markers of pregnenolone administration, which can potentially be abused by athletes to maintain an equilibration of the steroidal environment after sex steroids administrations. Patients with recurrent vulvovaginal candidiasis have significantly lower levels of urinary pregnanediol (PMID: 126703 , 16608896 , 16906539 , 1191599 , 2905284 , 15763596 , 10360427 , 11159778 , 16687200 ). Pregnanediol excretion is low in women with suspected placental insufficiency and in women with uterine fibroma. Pregnanediol levels can change in endocrine disturbances such as hirsutism or Cushing's syndrome, depending on the stage of the disease. Pregnanediol has been tried as a more reliable compound to measure in screening of urinary steroids when suspecting doping, due to its not significant isotopic fractionation that could lead to false positive results in anti-doping testing. 13C-Enrichment caused by a diet change might be a reason of concern in athletes that move around between places and might have a considerable change of diet between competitions. In contrast to the results obtained with the carbon isotopic ratio, the profiling of urinary testosterone/epitestosterone (T/E) ratios is found to be unaffected by a diet change (PMID: 16338181 , 5172227 , 13636945 , 14440289 ). |
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| Structure | [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)O InChI=1S/C21H36O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h13-19,22-23H,4-12H2,1-3H3/t13-,14+,15+,16-,17+,18-,19-,20-,21+/m0/s1 |
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| Synonyms | | Value | Source |
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| 5beta-Pregnane-3alpha,20alpha-diol | Kegg | | Pregnandiol | Kegg | | Diol | Kegg | | 5b-Pregnane-3a,20a-diol | Generator | | 5Β-pregnane-3α,20α-diol | Generator | | (3alpha,5beta,20S)-Pregnane-3,20-diol | HMDB | | (3Α,5β,20S)-pregnane-3,20-diol | HMDB | | 3alpha,20alpha-Dihydroxy-5beta-pregnane | HMDB | | 3Α,20α-dihydroxy-5β-pregnane | HMDB | | 5beta-Pregnanediol | HMDB | | 5Β-pregnanediol | HMDB | | Pregnanediol | HMDB |
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| Chemical Formula | C21H36O2 |
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| Average Molecular Weight | 320.517 |
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| Monoisotopic Molecular Weight | 320.271530399 |
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| IUPAC Name | (1S,2S,5R,7R,10R,11S,14S,15S)-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol |
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| Traditional Name | (1S,2S,5R,7R,10R,11S,14S,15S)-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol |
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| CAS Registry Number | 80-92-2 |
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| SMILES | [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)O |
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| InChI Identifier | InChI=1S/C21H36O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h13-19,22-23H,4-12H2,1-3H3/t13-,14+,15+,16-,17+,18-,19-,20-,21+/m0/s1 |
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| InChI Key | YWYQTGBBEZQBGO-BERLURQNSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Steroids and steroid derivatives |
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| Sub Class | Pregnane steroids |
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| Direct Parent | Gluco/mineralocorticoids, progestogins and derivatives |
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| Alternative Parents | |
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| Substituents | - Progestogin-skeleton
- 20-hydroxysteroid
- 3-alpha-hydroxysteroid
- Hydroxysteroid
- 3-hydroxysteroid
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Disposition | |
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| Physical Properties |
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| State | Solid |
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| Experimental Molecular Properties | | Property | Value | Reference |
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| Melting Point | 243.5 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Experimental Chromatographic Properties | Not Available |
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| Predicted Molecular Properties | |
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| Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized| Derivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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| Pregnanediol,1TMS,isomer #1 | C[C@H](O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C | 2779.7 | Semi standard non polar | 33892256 | | Pregnanediol,1TMS,isomer #2 | C[C@H](O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C | 2752.4 | Semi standard non polar | 33892256 | | Pregnanediol,2TMS,isomer #1 | C[C@H](O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C | 2777.8 | Semi standard non polar | 33892256 | | Pregnanediol,1TBDMS,isomer #1 | C[C@H](O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C | 3036.9 | Semi standard non polar | 33892256 | | Pregnanediol,1TBDMS,isomer #2 | C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C | 3001.1 | Semi standard non polar | 33892256 | | Pregnanediol,2TBDMS,isomer #1 | C[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C | 3298.6 | Semi standard non polar | 33892256 |
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| Disease References | | Schizophrenia |
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- Cai HL, Li HD, Yan XZ, Sun B, Zhang Q, Yan M, Zhang WY, Jiang P, Zhu RH, Liu YP, Fang PF, Xu P, Yuan HY, Zhang XH, Hu L, Yang W, Ye HS: Metabolomic analysis of biochemical changes in the plasma and urine of first-episode neuroleptic-naive schizophrenia patients after treatment with risperidone. J Proteome Res. 2012 Aug 3;11(8):4338-50. doi: 10.1021/pr300459d. Epub 2012 Jul 26. [PubMed:22800120 ]
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| General References | - Guedeney X, Chanez C, Grenier A, Scherrmann JM: Temperature-dependent immunoreactive assay to screen for digoxin-like immunoreactive factor(s). Clin Chem. 1991 Nov;37(11):1900-4. [PubMed:1718632 ]
- Schindler AE, Wuchter J: Studies on steroids in urine of the male newborn. Biol Neonate. 1975;27(3-4):192-207. [PubMed:126703 ]
- Seppala M, Ranta T, Hirvonen E: Hyperprolactinaemia and luteal insufficiency. Lancet. 1976 Jan 31;1(7953):229-30. [PubMed:55535 ]
- Oriol-Bosch A, Cortes J: Effects of postovulatory estradiol benzoate administration on women's ovarian function. Fertil Steril. 1975 May;26(5):405-12. [PubMed:1126465 ]
- Lewis JG, McGill H, Patton VM, Elder PA: Caution on the use of saliva measurements to monitor absorption of progesterone from transdermal creams in postmenopausal women. Maturitas. 2002 Jan 30;41(1):1-6. [PubMed:11809337 ]
- Dolz M, Acien P, Gomez-Capilla JA, Campos-Banales ME, Comino R: [The urinary excretion of pregnanediol during pregnancy determined by gas-liquid chromatography. II. Its relation with other parameters controling pregnancy (author's transl)]. Reproduccion. 1976 Jul-Dec;3(3-4):219-26. [PubMed:1032593 ]
- Metcalf MG, Evans JJ, Mackenzie JA: Indices of ovulation: comparison of plasma and salivary levels of progesterone with urinary pregnanediol. J Endocrinol. 1984 Jan;100(1):75-80. [PubMed:6690646 ]
- Kravitz HM, Janssen I, Santoro N, Bromberger JT, Schocken M, Everson-Rose SA, Karavolos K, Powell LH: Relationship of day-to-day reproductive hormone levels to sleep in midlife women. Arch Intern Med. 2005 Nov 14;165(20):2370-6. [PubMed:16287766 ]
- Yong EL, Glasier A, Hillier H, Ledger W, Caird L, Beattie G, Sweeting V, Thong J, Baird DT: Effect of cyclofenil on hormonal dynamics, follicular development and cervical mucus in normal and oligomenorrhoeic women. Hum Reprod. 1992 Jan;7(1):39-43. [PubMed:1551955 ]
- Croxatto HB, Diaz S: The place of progesterone in human contraception. J Steroid Biochem. 1987;27(4-6):991-4. [PubMed:3320572 ]
- Reutman SR, LeMasters GK, Kesner JS, Shukla R, Krieg EF Jr, Knecht EA, Lockey JE: Urinary reproductive hormone level differences between African American and Caucasian women of reproductive age. Fertil Steril. 2002 Aug;78(2):383-91. [PubMed:12137878 ]
- Nemoto Y, Saibara T, Ogawa Y, Zhang T, Xu N, Ono M, Akisawa N, Iwasaki S, Maeda T, Onishi S: Tamoxifen-induced nonalcoholic steatohepatitis in breast cancer patients treated with adjuvant tamoxifen. Intern Med. 2002 May;41(5):345-50. [PubMed:12058881 ]
- Hargreaves T, Piper RF: Breast milk jaundice. Effect of inhibitory breast milk and 3 alpha, 20 abeta-pregnanediol on glucuronyl transferase. Arch Dis Child. 1971 Apr;46(246):195-8. [PubMed:5576030 ]
- Joseph-Horne R, Mason H, Batty S, White D, Hillier S, Urquhart M, Franks S: Luteal phase progesterone excretion in ovulatory women with polycystic ovaries. Hum Reprod. 2002 Jun;17(6):1459-63. [PubMed:12042261 ]
- Saudan C, Kamber M, Barbati G, Robinson N, Desmarchelier A, Mangin P, Saugy M: Longitudinal profiling of urinary steroids by gas chromatography/combustion/isotope ratio mass spectrometry: diet change may result in carbon isotopic variations. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Feb 2;831(1-2):324-7. Epub 2005 Dec 9. [PubMed:16338181 ]
- Homma K, Hasegawa T, Nagai T, Adachi M, Horikawa R, Fujiwara I, Tajima T, Takeda R, Fukami M, Ogata T: Urine steroid hormone profile analysis in cytochrome P450 oxidoreductase deficiency: implication for the backdoor pathway to dihydrotestosterone. J Clin Endocrinol Metab. 2006 Jul;91(7):2643-9. Epub 2006 Apr 11. [PubMed:16608896 ]
- Williamson L, Arlt W, Shackleton C, Kelley RI, Braddock SR: Linking Antley-Bixler syndrome and congenital adrenal hyperplasia: a novel case of P450 oxidoreductase deficiency. Am J Med Genet A. 2006 Sep 1;140A(17):1797-803. [PubMed:16906539 ]
- Duff GB: Prognosis in threatened abortion: a comparison between predictions made by sonar urinary hormone assays and clinical judgement. Br J Obstet Gynaecol. 1975 Nov;82(11):858-62. [PubMed:1191599 ]
- Ishwad PC, Chitlange SM, Joshi UM, Chowdhury V, Mehta AC: Urinary estrone glucuronide, pregnanediol glucuronide and human chorionic gonadotrophin in threatened abortion. Int J Gynaecol Obstet. 1988 Aug;27(1):107-11. [PubMed:2905284 ]
- Saudan C, Desmarchelier A, Sottas PE, Mangin P, Saugy M: Urinary marker of oral pregnenolone administration. Steroids. 2005 Mar;70(3):179-83. [PubMed:15763596 ]
- Aguilera R, Catlin DH, Becchi M, Phillips A, Wang C, Swerdloff RS, Pope HG, Hatton CK: Screening urine for exogenous testosterone by isotope ratio mass spectrometric analysis of one pregnanediol and two androstanediols. J Chromatogr B Biomed Sci Appl. 1999 Apr 30;727(1-2):95-105. [PubMed:10360427 ]
- Aguilera R, Chapman TE, Starcevic B, Hatton CK, Catlin DH: Performance characteristics of a carbon isotope ratio method for detecting doping with testosterone based on urine diols: controls and athletes with elevated testosterone/epitestosterone ratios. Clin Chem. 2001 Feb;47(2):292-300. [PubMed:11159778 ]
- Spacek J, Buchta V, Jilek P, Forstl M: Clinical aspects and luteal phase assessment in patients with recurrent vulvovaginal candidiasis. Eur J Obstet Gynecol Reprod Biol. 2007 Apr;131(2):198-202. Epub 2006 May 9. [PubMed:16687200 ]
- Modignani RL: [Hirsutism: metabolic and clinical problems]. Folia Endocrinol. 1971 Oct-Dec;24(5):385-92. [PubMed:5172227 ]
- UTOCHNIKOVA NS, SYCH LD: [Content of estrogens, pregnandiol and 17-ketosteroids in urine of women with fibromyoma of the uterus]. Akush Ginekol (Mosk). 1959 Mar-Apr;35(2):16-20. [PubMed:13636945 ]
- RUSSELL CS, DEWHURST CJ, BLAKEY DH: The pregnanediol excretion in suspected placental insufficiency. J Obstet Gynaecol Br Emp. 1960 Feb;67:1-10. [PubMed:14440289 ]
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