You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2006-05-22 15:12:30 UTC
Update Date2016-05-20 17:21:00 UTC
HMDB IDHMDB03069
Secondary Accession NumbersNone
Metabolite Identification
Common Name20a-Dihydroprogesterone
Description20a-Dihydroprogesterone is a biologically active 20-alpha-reduced metabolite of progesterone. It is converted from progesterone to 20-alpha-hydroxypregn-4-en-3-one by the 20-alpha-hydroxysteroid dehydrogenase in the corpus luteum and the placenta. -- Pubchem; Progesterone is a C-21 steroid hormone involved in the female menstrual cycle, pregnancy (supports gestation) and embryogenesis of humans and other species. Progesterone belongs to a class of hormones called progestagens, and is the major naturally occurring human progestagen. -- Wikipedia; During implantation and gestation, progesterone appears to decrease the maternal immune response to allow for the acceptance of the pregnancy. Progesterone decreases contractility of the uterine smooth muscle. The fetus metabolizes placental progesterone in the production of adrenal mineralo- and glucosteroids. A drop in progesterone levels is possibly one step that facilitates the onset of labor. In addition progesterone inhibits lactation during pregnancy. The fall in progesterone levels following delivery is one of the triggers for milk production. -- Wikipedia.
Structure
Thumb
Synonyms
ValueSource
20beta-DihydroprogesteroneChEBI
20beta-Hydroxy-4-pregnen-3-oneChEBI
20beta-Hydroxypregn-4-en-3-oneChEBI
20b-DihydroprogesteroneGenerator
20β-dihydroprogesteroneGenerator
20b-Hydroxy-4-pregnen-3-oneGenerator
20β-hydroxy-4-pregnen-3-oneGenerator
20b-Hydroxypregn-4-en-3-oneGenerator
20β-hydroxypregn-4-en-3-oneGenerator
(20S)-20-Hydroxypregn-4-en-3-oneHMDB
20(S)-HydroxyprogesteroneHMDB
20-a-DihydroprogesteroneHMDB
20-alpha-DihydroprogesteroneHMDB
20-alpha-HydroxydihydroprogesteroneHMDB
20-alpha-HydroxyprogesteroneHMDB
20-alpha-ProgerolHMDB
20a-HydroxydihydroprogesteroneHMDB
20a-Hydroxypreg-4-en-3-oneHMDB
20a-Hydroxypregnen-2-oneHMDB
20a-HydroxyprogesteroneHMDB
20a-ProgerolHMDB
20alpha-DihydroprogesteroneHMDB
20alpha-DihydroprognenoloneHMDB
20alpha-Hydroxy-4-pregnen-3-oneHMDB
20alpha-HydroxydihydroprogesteroneHMDB
20alpha-Hydroxypreg-4-en-3-oneHMDB
20alpha-Hydroxypregn-4-en-3-oneHMDB
20alpha-Hydroxypregnen-2-oneHMDB
20alpha-HydroxyprogesteroneHMDB
20alpha-ProgerolHMDB
DihydrogesteroneHMDB
DihydroxyprogesteroneHMDB
Progesterol-20-alphaHMDB
Progesterol-20aHMDB
Chemical FormulaC21H32O2
Average Molecular Weight316.4776
Monoisotopic Molecular Weight316.240230268
IUPAC Name(1S,2R,10S,11S,14S,15S)-14-[(1R)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Name20β-dihydroprogesterone
CAS Registry Number145-14-2
SMILES
[H][C@@]12CC[C@H]([C@@H](C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C21H32O2/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/h12-13,16-19,22H,4-11H2,1-3H3/t13-,16+,17-,18+,19+,20+,21-/m1/s1
InChI KeyInChIKey=RWBRUCCWZPSBFC-SJOKZOANSA-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
  • 20-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • 20-hydroxypregn-4-en-3-one (CHEBI:36729 )
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030153 )
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
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point126 - 131 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.01 mg/mLALOGPS
logP3.52ALOGPS
logP3.94ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)19ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity93.73 m3·mol-1ChemAxon
Polarizability37.82 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Placenta
  • Testes
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0199 (0.0190-0.0208) uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0164 (0.0126 - 0.0199) uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0731 (0.0199 -0.1263) uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.0070 (0.0008 - 0.0117) uMAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023103
KNApSAcK IDNot Available
Chemspider ID83725
KEGG Compound IDC04042
BioCyc IDNot Available
BiGG ID43018
Wikipedia Link20-alpha-Dihydroprogesterone
NuGOwiki LinkHMDB03069
Metagene LinkHMDB03069
METLIN ID2125
PubChem Compound92747
PDB IDNot Available
ChEBI ID36729
References
Synthesis ReferenceSanai Y; Suzuki T; Yanaihara T; Nakayama T 20 alpha-Dihydropregnenolone-sulfate and 20 alpha-dihydroprogesterone biosynthesis and metabolism in feto-placental unit. Nippon Sanka Fujinka Gakkai zasshi (1984), 36(2), 195-201.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Rovensky J, Radikova Z, Imrich R, Greguska O, Vigas M, Macho L: Gonadal and adrenal steroid hormones in plasma and synovial fluid of patients with rheumatoid arthritis. Endocr Regul. 2004 Dec;38(4):143-9. [15841793 ]
  2. Kaaks R, Berrino F, Key T, Rinaldi S, Dossus L, Biessy C, Secreto G, Amiano P, Bingham S, Boeing H, Bueno de Mesquita HB, Chang-Claude J, Clavel-Chapelon F, Fournier A, van Gils CH, Gonzalez CA, Gurrea AB, Critselis E, Khaw KT, Krogh V, Lahmann PH, Nagel G, Olsen A, Onland-Moret NC, Overvad K, Palli D, Panico S, Peeters P, Quiros JR, Roddam A, Thiebaut A, Tjonneland A, Chirlaque MD, Trichopoulou A, Trichopoulos D, Tumino R, Vineis P, Norat T, Ferrari P, Slimani N, Riboli E: Serum sex steroids in premenopausal women and breast cancer risk within the European Prospective Investigation into Cancer and Nutrition (EPIC). J Natl Cancer Inst. 2005 May 18;97(10):755-65. [15900045 ]
  3. Reinberg A, Smolensky MH, Hallek M, Smith KD, Steinberger E: Annual variation in semen characteristics and plasma hormone levels in men undergoing vasectomy. Fertil Steril. 1988 Feb;49(2):309-15. [3123279 ]
  4. Piasek M, Gomzi M: [Environmental tobacco smoke and children: assessment of exposure and health effects] Lijec Vjesn. 2004 Nov-Dec;126(11-12):325-30. [16082891 ]
  5. Suzuki T, Hirato K, Ogawa K, Yanaihara T, Nakayama T: [Changes in steroids in amniotic fluid in relation to the initiation of labor] Nippon Sanka Fujinka Gakkai Zasshi. 1984 Oct;36(10):1841-50. [6238997 ]
  6. Kalinka J, Szekeres-Bartho J: The impact of dydrogesterone supplementation on hormonal profile and progesterone-induced blocking factor concentrations in women with threatened abortion. Am J Reprod Immunol. 2005 Apr;53(4):166-71. [15760377 ]
  7. Raja A, Hashmi SN, Sultana N, Rashid H: Presentation of polycystic ovary syndrome and its management with clomiphene alone and in combination with metformin. J Ayub Med Coll Abbottabad. 2005 Apr-Jun;17(2):50-3. [16092652 ]
  8. Ma H, Penning TM: Conversion of mammalian 3alpha-hydroxysteroid dehydrogenase to 20alpha-hydroxysteroid dehydrogenase using loop chimeras: changing specificity from androgens to progestins. Proc Natl Acad Sci U S A. 1999 Sep 28;96(20):11161-6. [10500147 ]
  9. Stranahan D, Rausch D, Deng A, Gaspari A: The role of intradermal skin testing and patch testing in the diagnosis of autoimmune progesterone dermatitis. Dermatitis. 2006 Mar;17(1):39-42. [16800278 ]
  10. Stachenfeld NS, Taylor HS: Progesterone increases plasma volume independent of estradiol. J Appl Physiol. 2005 Jun;98(6):1991-7. Epub 2005 Feb 17. [15718411 ]
  11. Kenis I, Tartakover-Matalon S, Cherepnin N, Drucker L, Fishman A, Pomeranz M, Lishner M: Simvastatin has deleterious effects on human first trimester placental explants. Hum Reprod. 2005 Oct;20(10):2866-72. Epub 2005 Jun 15. [15958395 ]
  12. Nichols AA: Cholestasis of pregnancy: a review of the evidence. J Perinat Neonatal Nurs. 2005 Jul-Sep;19(3):217-25. [16106229 ]
  13. Bruno-Ambrosius K, Yucel-Lindberg T, Twetman S: Salivary buffer capacity in relation to menarche and progesterone levels in saliva from adolescent girls: a longitudinal study. Acta Odontol Scand. 2004 Oct;62(5):269-72. [15841814 ]
  14. Nielsen FH: The alteration of magnesium, calcium and phosphorus metabolism by dietary magnesium deprivation in postmenopausal women is not affected by dietary boron deprivation. Magnes Res. 2004 Sep;17(3):197-210. [15724868 ]
  15. Stanczyk FZ, Paulson RJ, Roy S: Percutaneous administration of progesterone: blood levels and endometrial protection. Menopause. 2005 Mar;12(2):232-7. [15772572 ]
  16. Seppala M, Ranta T, Hirvonen E: Hyperprolactinaemia and luteal insufficiency. Lancet. 1976 Jan 31;1(7953):229-30. [55535 ]
  17. Rovensky J, Kvetnansky R, Radikova Z, Imrich R, Greguska O, Vigas M, Macho L: Hormone concentrations in synovial fluid of patients with rheumatoid arthritis. Clin Exp Rheumatol. 2005 May-Jun;23(3):292-6. [15971415 ]
  18. THOMAS GH: Ketonic metabolites of progesterone and 19-norprogesterone in rabbit urine. Biochem J. 1962 Jun;83:450-5. [13920778 ]
  19. Casey ML, MacDonald PC: Metabolism of deoxycorticosterone and deoxycorticosterone sulfate in men and women. J Clin Invest. 1982 Aug;70(2):312-9. [7096569 ]
  20. Grissom FE, Brooks CL, Littleton GK: The effect of placenta on lactogen receptor in pseudopregnant rabbits. Endocr Res. 1990;16(1):51-75. [2158435 ]
  21. Lappas M, Yee K, Permezel M, Rice GE: Release and regulation of leptin, resistin and adiponectin from human placenta, fetal membranes, and maternal adipose tissue and skeletal muscle from normal and gestational diabetes mellitus-complicated pregnancies. J Endocrinol. 2005 Sep;186(3):457-65. [16135665 ]
  22. Hosaka M, Oshima H, Nankin H, Troen P: Studies of the human testis. XI. Leydig cell clusters and levels of intratesticular testosterone and 20 alpha-dihydroprogesterone. J Clin Endocrinol Metab. 1978 Nov;47(5):1164-7. [263345 ]
  23. Longcope C, Franz C, Morello C, Baker R, Johnston CC Jr: Steroid and gonadotropin levels in women during the peri-menopausal years. Maturitas. 1986 Oct;8(3):189-96. [3097458 ]
  24. Halari R, Hines M, Kumari V, Mehrotra R, Wheeler M, Ng V, Sharma T: Sex differences and individual differences in cognitive performance and their relationship to endogenous gonadal hormones and gonadotropins. Behav Neurosci. 2005 Feb;119(1):104-17. [15727517 ]
  25. Tuckey RC: Progesterone synthesis by the human placenta. Placenta. 2005 Apr;26(4):273-81. [15823613 ]
  26. Auge AP, Longui CA, Almeida Prado RA, Rocha MN, Hirota A, Busso NE, Monte O, Aldrighi JM: Abnormal inhibin A and inhibin B secretion in obese women with and without insulin resistance. Gynecol Endocrinol. 2005 Jul;21(1):7-11. [16048795 ]
  27. Kivlighan KT, Granger DA, Schwartz EB: Blood contamination and the measurement of salivary progesterone and estradiol. Horm Behav. 2005 Mar;47(3):367-70. [15708767 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the intrahepatic bile acid concentration. Has a low bile-binding ability. May play a role in myelin formation.
Gene Name:
AKR1C1
Uniprot ID:
Q04828
Molecular weight:
36788.02