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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 09:17:15 UTC
Update Date2020-05-13 16:12:26 UTC
HMDB IDHMDB0004025
Secondary Accession Numbers
  • HMDB0005943
  • HMDB04025
  • HMDB05943
Metabolite Identification
Common NamePregnanediol
DescriptionPregnanediol 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 ).
Structure
Data?1589386346
Synonyms
ValueSource
DiolKegg
5beta-Pregnane-3alpha,20alpha-diolKegg
PregnandiolKegg
5b-Pregnane-3a,20a-diolGenerator
5Β-pregnane-3α,20α-diolGenerator
(3alpha,5beta,20S)-Pregnane-3,20-diolHMDB
(3α,5β,20S)-Pregnane-3,20-diolHMDB
3alpha,20alpha-Dihydroxy-5beta-pregnaneHMDB
3α,20α-Dihydroxy-5β-pregnaneHMDB
5beta-PregnanediolHMDB
5β-PregnanediolHMDB
PregnanediolHMDB
Chemical FormulaC21H36O2
Average Molecular Weight320.517
Monoisotopic Molecular Weight320.271530399
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
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
CAS Registry Number80-92-2
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
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
InChI KeyYWYQTGBBEZQBGO-BERLURQNSA-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-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point243.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00052 g/LALOGPS
logP4.35ALOGPS
logP3.78ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-0.87ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity93.93 m³·mol⁻¹ChemAxon
Polarizability39.1 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0049000000-bd41f0c790337473e5acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0496000000-6685cf85a653eddaee68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0550-1590000000-5a35883cc16aa60a150aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-369d0ceac1cc91054484Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-0039000000-216a9cda912ba69dda81Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-0092000000-8861e9a22f55c5c0f2c3Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Urine
Tissue Locations
  • Liver
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.12 (0.032-0.21) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.25 (0.046-0.46) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Schizophrenia
details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. 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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023280
KNApSAcK IDNot Available
Chemspider ID190585
KEGG Compound IDC05484
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPregnanediol
METLIN IDNot Available
PubChem Compound219833
PDB IDNot Available
ChEBI ID8387
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis Referencetoh, Shinji; Ichikawa, Harumi; Takagi, Hidetoshi; Yoshizawa, Itsuo. Clinical analysis on steroids. XLII. On the rearrangement reactions of pregnanediol disulfate to D13-steroid, and its 20-isomeric sulfate to D-homosteroids. Chemical & Pharmaceutical Bull
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. Seppala M, Ranta T, Hirvonen E: Hyperprolactinaemia and luteal insufficiency. Lancet. 1976 Jan 31;1(7953):229-30. [PubMed:55535 ]
  8. Croxatto HB, Diaz S: The place of progesterone in human contraception. J Steroid Biochem. 1987;27(4-6):991-4. [PubMed:3320572 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. Schindler AE, Wuchter J: Studies on steroids in urine of the male newborn. Biol Neonate. 1975;27(3-4):192-207. [PubMed:126703 ]
  15. 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 ]
  16. 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 ]
  17. 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 ]
  18. 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 ]
  19. 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 ]
  20. 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 ]
  21. 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 ]
  22. 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 ]
  23. 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 ]
  24. Modignani RL: [Hirsutism: metabolic and clinical problems]. Folia Endocrinol. 1971 Oct-Dec;24(5):385-92. [PubMed:5172227 ]
  25. 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 ]
  26. 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 ]