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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-01-11 19:15:19 UTC
HMDB IDHMDB0000920
Secondary Accession Numbers
  • HMDB00920
Metabolite Identification
Common Name11a-Hydroxyprogesterone
DescriptionProgesterone 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; Progesterone's reproductive function serves to convert the endometrium to its secretory stage to prepare the uterus for implantation. If pregnancy does not occur, progesterone levels will decrease leading to menstruation in the human. Normal menstrual bleeding is a progesterone withdrawal bleeding. -- 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 musculature. 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. Progesterone has an effect upon vaginal epithelium and cervical mucus. -- Wikipedia.
Structure
Data?1547234119
Synonyms
ValueSource
11-HydroxyprogesteroneHMDB
11a-Hydroxy-pregn-4-ene-3,20-dioneHMDB
11a-Hydroxy-progesteroneHMDB
11a-Hydroxypregn-4-ene-3,20-dioneHMDB
4-Pregnene-11a-ol-3,20-dioneHMDB
Pregn-4-en-11a-ol-3,20-dioneHMDB
Chemical FormulaC21H30O3
Average Molecular Weight330.4611
Monoisotopic Molecular Weight330.219494826
IUPAC Name(1S,2R,10S,11S,15S,17R)-14-acetyl-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Nameduralutin
CAS Registry Number312-90-3
SMILES
[H][C@@]12CCC(C(C)=O)[C@@]1(C)C[C@@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C21H30O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h10,15-19,24H,4-9,11H2,1-3H3/t15-,16?,17-,18+,19+,20-,21+/m0/s1
InChI KeyBFZHCUBIASXHPK-ODYOLWGQSA-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-oxosteroid
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • 11-hydroxysteroid
  • 11-alpha-hydroxysteroid
  • Hydroxysteroid
  • Oxosteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point222 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.05 mg/mLNot Available
LogP2.36HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.036 g/LALOGPS
logP2.65ALOGPS
logP2.84ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)18.88ChemAxon
pKa (Strongest Basic)-0.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity94.3 m³·mol⁻¹ChemAxon
Polarizability37.69 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-060c-1953000000-b1a4b33b602a8015fa69View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00ei-2429000000-079db188a5d002efdb6bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0009000000-3dea6ae65884847d2d23View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-3920000000-f68bb1cfb59fc92b2b29View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-006y-9800000000-c9be24b1a08fbdae7688View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0019000000-bf6b2487f64f20d9b0bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ej-0396000000-92a340550f7481b38022View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfu-4191000000-1c0ef35ebf478850133dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-f02ca96a4e201dad8f5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0019000000-394e7b1e14943d144acfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dr-1195000000-470cc2622e09566ebf95View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022318
KNApSAcK IDNot Available
Chemspider ID389106
KEGG Compound IDC03747
BioCyc IDCPD-272
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5873
PubChem Compound440105
PDB IDNot Available
ChEBI ID16076
References
Synthesis Reference11b-Hydroxylation of steroids. (1957), GB 769999 19570313 CAN 51:64205 AN 1957:64205
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Blau N, Zachmann M, Kempken B, Staudenmann W, Mohr E, Curtius HC: Identification of new steroids in patients with 17 alpha-hydroxylase deficiency by capillary gas chromatography/mass spectrometry. Biomed Environ Mass Spectrom. 1987 Nov;14(11):633-7. [PubMed:2962669 ]
  2. van der Willigen AH, Peereboom-Wynia JD, van Joost T, Stolz E: A preliminary study of the effect of 11a-hydroxyprogesterone on the hair growth in men suffering from androgenetic alopecia. Acta Derm Venereol. 1987;67(1):82-5. [PubMed:2436423 ]
  3. Iudaev NA, Afinogenova SA: [Pathways of corticosteroid biosynthesis in human adrenals (Itsenko-Cushing disease)]. Biokhimiia. 1976 Sep;41(9):1619-27. [PubMed:974176 ]