20alpha-Dihydroprogesterone (CHEM035490)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:48:45 UTC
Update Date2016-11-09 01:21:19 UTC
Accession NumberCHEM035490
Identification
Common Name20alpha-Dihydroprogesterone
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
DihydrogesteroneHMDB
DihydroxyprogesteroneHMDB
DihydroprogesteroneHMDB
AlgestoneHMDB
Chemical FormulaC21H32O2
Average Molecular Mass316.478 g/mol
Monoisotopic Mass316.240 g/mol
CAS Registry Number145-15-3
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
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 IdentifierInChI=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 KeyRWBRUCCWZPSBFC-SJOKZOANSA-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-oxo-delta-4-steroid
  • 3-oxosteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • 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 )
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.01 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity93.73 m³·mol⁻¹ChemAxon
Polarizability37.82 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f7c-0292000000-03a07f8203a9b7f67d77Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-1109000000-f635b6b1379b4893847eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0195000000-cd14d0a9b396d1886f70Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00r2-0291000000-72c03508cdbc1340973cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-1390000000-9a6c725ff5d5fe520854Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-956e134c91b73d3e76a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0089000000-58474d2a0b2805be7785Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0597-0090000000-ee4f46fc804ae52ca359Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID43018
BioCyc IDNot Available
METLIN ID2125
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID83725
ChEBI ID36729
PubChem Compound ID92747
Kegg Compound IDC04042
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Sanai 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.
2. Sanai 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.
3. 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.
4. 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.
5. 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.
6. 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.
7. Suzuki T, Hirato K, Ogawa K, Yanaihara T, Nakayama T: [Changes in steroids in amniotic fluid in relation to the initiation of labor]. Nihon Sanka Fujinka Gakkai Zasshi. 1984 Oct;36(10):1841-50.
8. 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.
9. 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.
10. 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.
11. 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.
12. Stachenfeld NS, Taylor HS: Progesterone increases plasma volume independent of estradiol. J Appl Physiol (1985). 2005 Jun;98(6):1991-7. Epub 2005 Feb 17.
13. 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.
14. Nichols AA: Cholestasis of pregnancy: a review of the evidence. J Perinat Neonatal Nurs. 2005 Jul-Sep;19(3):217-25.
15. 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.
16. 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.
17. Stanczyk FZ, Paulson RJ, Roy S: Percutaneous administration of progesterone: blood levels and endometrial protection. Menopause. 2005 Mar;12(2):232-7.
18. Seppala M, Ranta T, Hirvonen E: Hyperprolactinaemia and luteal insufficiency. Lancet. 1976 Jan 31;1(7953):229-30.
19. 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.
20. THOMAS GH: Ketonic metabolites of progesterone and 19-norprogesterone in rabbit urine. Biochem J. 1962 Jun;83:450-5.
21. Casey ML, MacDonald PC: Metabolism of deoxycorticosterone and deoxycorticosterone sulfate in men and women. J Clin Invest. 1982 Aug;70(2):312-9.
22. Grissom FE, Brooks CL, Littleton GK: The effect of placenta on lactogen receptor in pseudopregnant rabbits. Endocr Res. 1990;16(1):51-75.
23. 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.
24. 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.
25. 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.
26. 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.
27. Tuckey RC: Progesterone synthesis by the human placenta. Placenta. 2005 Apr;26(4):273-81.
28. 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.
29. Kivlighan KT, Granger DA, Schwartz EB: Blood contamination and the measurement of salivary progesterone and estradiol. Horm Behav. 2005 Mar;47(3):367-70.