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Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2016-02-11 01:28:49 UTC
HMDB IDHMDB14522
Secondary Accession NumbersNone
Metabolite Identification
Common NameDydrogesterone
DescriptionDydrogesterone is only found in individuals that have used or taken this drug. It is a synthetic progestational hormone with no androgenic or estrogenic properties. Unlike many other progestational compounds, dydrogesterone produces no increase in temperature and does not inhibit ovulation. [PubChem]Dydrogesterone works by regulating the healthy growth and normal shedding of the womb lining by acting on progesterone receptors in the uterus.
Structure
Thumb
Synonyms
ValueSource
10alpha-IsopregnenoneChEBI
6-dehydro-retro-ProgesteroneChEBI
delta(6)-RetroprogesteroneChEBI
DidrogesteronaChEBI
DydrogesteronumChEBI
HydrogesteroneChEBI
HydrogestroneChEBI
IsopregnenoneChEBI
retro-6-DehydroprogesteroneChEBI
10a-IsopregnenoneGenerator
10α-isopregnenoneGenerator
δ(6)-retroprogesteroneGenerator
DidrogesteroneHMDB
Chemical FormulaC21H28O2
Average Molecular Weight312.4458
Monoisotopic Molecular Weight312.20893014
IUPAC Name(1R,2S,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-5-one
Traditional Namedydrogesterone
CAS Registry Number152-62-5
SMILES
[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@@]12C
InChI Identifier
InChI=1S/C21H28O2/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/h4-5,12,16-19H,6-11H2,1-3H3/t16-,17+,18-,19+,20+,21+/m0/s1
InChI KeyInChIKey=JGMOKGBVKVMRFX-HQZYFCCVSA-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
  • Oxosteroid
  • 3-oxosteroid
  • Cyclic ketone
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Pregnadien derivatives
  • Progesterones
  • Progestins
Application
  • Nutrients
  • Pharmaceutical
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point169.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.86e-03 g/LNot Available
LogP3.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0049 mg/mLALOGPS
logP3.27ALOGPS
logP3.79ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)19.29ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity93.82 m3·mol-1ChemAxon
Polarizability36.39 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
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00378
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00378
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00378
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8699
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDydrogesterone
NuGOwiki LinkHMDB14522
Metagene LinkHMDB14522
METLIN IDNot Available
PubChem Compound9051
PDB IDNot Available
ChEBI ID31527
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Patient.co.uk [Link]

Enzymes

General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Isoform A is inactive in stimulating c-Src/MAPK signaling on hormone stimulation
Gene Name:
PGR
Uniprot ID:
P06401
Molecular weight:
98980.0
References
  1. Blois SM, Joachim R, Kandil J, Margni R, Tometten M, Klapp BF, Arck PC: Depletion of CD8+ cells abolishes the pregnancy protective effect of progesterone substitution with dydrogesterone in mice by altering the Th1/Th2 cytokine profile. J Immunol. 2004 May 15;172(10):5893-9. [15128769 ]
  2. Tamaya T, Tsurusaki T, Ide N, Yamada T, Murakami T, Wada K, Fujimoto Z, Okada H: Nuclear translocation of progesterone receptor--progestogen complex in vitro. Nihon Sanka Fujinka Gakkai Zasshi. 1983 Jan;35(1):77-82. [6827166 ]
  3. Raghupathy R, Al Mutawa E, Makhseed M, Azizieh F, Szekeres-Bartho J: Modulation of cytokine production by dydrogesterone in lymphocytes from women with recurrent miscarriage. BJOG. 2005 Aug;112(8):1096-101. [16045524 ]
  4. Okada H: [Metabolism, structure and biological activity of sex steroids]. Nihon Naibunpi Gakkai Zasshi. 1993 Feb 20;69(2):67-79. [8486204 ]
  5. Tamaya T, Furuta N, Ohono Y, Ide N, Tsurusaki T, Okada H: Chromatin transcription by progesterone-receptor complex in rabbit uterus. Endocrinol Jpn. 1979 Feb;26(1):117-22. [436795 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]