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Record Information
Version3.6
Creation Date2006-08-13 09:17:15 UTC
Update Date2016-10-18 22:50:18 UTC
HMDB IDHMDB04025
Secondary Accession NumbersNone
Metabolite Identification
Common NamePregnanediol
DescriptionPregnanediol is an endogenous human testosterone metabolite. It can be detected in adults and newborns urine 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 abortion in 74 - 93% per cent 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 ).
Structure
Thumb
Synonyms
ValueSource
(3a,5b,20S)-Pregnane-3,20-diolHMDB
3a,20a-Dihydroxy-5b-pregnaneHMDB
5b-Pregnane-3a,20a-diolHMDB
5beta-Pregnane-3alpha,20 alpha-diolHMDB
PregnandiolHMDB
Chemical FormulaC21H36O2
Average Molecular Weight320.5093
Monoisotopic Molecular Weight320.271530396
IUPAC Name(1S,2S,10S,11S,14S,15R)-14-ethyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,5-diol
Traditional Name5b-pregnane-3a,20a-diol
CAS Registry Number80-92-2
SMILES
[H][C@@]12CC[C@H](CC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)(O)CC[C@]12C
InChI Identifier
InChI=1S/C21H36O2/c1-4-14-6-8-17-16-7-5-15-13-21(22,23)12-11-20(15,3)18(16)9-10-19(14,17)2/h14-18,22-23H,4-13H2,1-3H3/t14-,15?,16-,17-,18-,19+,20-/m0/s1
InChI KeyInChIKey=JBSVQUOGNMYMSF-CIQUAOMQSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • 3-beta-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • 1,1-diol
  • Carbonyl hydrate
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected 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
StateSolid
Experimental Properties
PropertyValueReference
Melting Point243.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.000523 mg/mLALOGPS
logP4.79ALOGPS
logP4.52ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)12.03ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity93.95 m3·mol-1ChemAxon
Polarizability39.58 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Urine
Tissue Location
  • Liver
  • Spleen
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot ApplicableAdult (>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
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot ApplicableAdult (>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. [22800120 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023280
KNApSAcK IDNot Available
Chemspider ID2297701
KEGG Compound IDC05484
BioCyc IDPREGNANEDIOL
BiGG IDNot Available
Wikipedia LinkDiol
NuGOwiki LinkHMDB04025
Metagene LinkHMDB04025
METLIN ID7001
PubChem Compound3032822
PDB IDNot Available
ChEBI 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. 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. [1718632 ]
  2. Schindler AE, Wuchter J: Studies on steroids in urine of the male newborn. Biol Neonate. 1975;27(3-4):192-207. [126703 ]
  3. Seppala M, Ranta T, Hirvonen E: Hyperprolactinaemia and luteal insufficiency. Lancet. 1976 Jan 31;1(7953):229-30. [55535 ]
  4. Oriol-Bosch A, Cortes J: Effects of postovulatory estradiol benzoate administration on women's ovarian function. Fertil Steril. 1975 May;26(5):405-12. [1126465 ]
  5. 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. [11809337 ]
  6. 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. [1032593 ]
  7. 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. [6690646 ]
  8. 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. [16287766 ]
  9. 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. [1551955 ]
  10. Croxatto HB, Diaz S: The place of progesterone in human contraception. J Steroid Biochem. 1987;27(4-6):991-4. [3320572 ]
  11. 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. [12137878 ]
  12. 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. [12058881 ]
  13. 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. [5576030 ]
  14. 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. [12042261 ]
  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. [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. [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. [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. [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. [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. [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. [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. [16687200 ]