Showing metabocard for 5a-Pregnane-3,20-dione (BMDB0003759)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:06:02 UTC
Update Date2020-05-11 20:56:18 UTC
BMDB IDBMDB0003759
Secondary Accession Numbers
  • BMDB03759
Metabolite Identification
Common Name5a-Pregnane-3,20-dione
Description5a-5a-5a-pregnane-3,20-dione, also known as 5a-5a-pregnane-3,20-dione or 5a-5a-pregnane-3,20-dione, 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. Thus, 5a-5a-pregnane-3,20-dione is considered to be a steroid lipid molecule. 5a-5a-5a-pregnane-3,20-dione exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 5a-5a-5a-pregnane-3,20-dione exists in all living organisms, ranging from bacteria to humans. 5a-5a-5a-pregnane-3,20-dione participates in a number of enzymatic reactions, within cattle. In particular, 5a-5a-5a-pregnane-3,20-dione can be biosynthesized from progesterone; which is catalyzed by the enzyme 3-oxo-5-beta-steroid 4-dehydrogenase. In addition, 5a-5a-5a-pregnane-3,20-dione can be biosynthesized from 3a-hydroxy-5b-pregnane-20-one; which is catalyzed by the enzyme aldo-keto reductase family 1 member C4. In cattle, 5a-5a-pregnane-3,20-dione is involved in the metabolic pathway called the steroidogenesis pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,20-AllopregnanedioneChEBI
3,20-Dioxo-5alpha-pregnaneChEBI
5-alpha-DihydroprogesteroneChEBI
5alpha-DihydroprogesteroneChEBI
3,20-Dioxo-5a-pregnaneGenerator
3,20-Dioxo-5α-pregnaneGenerator
5-a-DihydroprogesteroneGenerator
5-Α-dihydroprogesteroneGenerator
5a-DihydroprogesteroneGenerator
5Α-dihydroprogesteroneGenerator
5-alpha-Pregnane-3,20-dioneHMDB, MeSH
5a-Pregnan-3,20-dioneHMDB
5alpha-Pregnan-3,20-dioneHMDB
5alpha-Pregnane-3,20-dioneHMDB, MeSH
5b-Pregnane-3,20-dioneHMDB
5beta-Pregnane-3,20-dioneHMDB
Allopregnan-3,20-dioneHMDB
Pregnane-3,20-dioneHMDB
5 alpha DihydroprogesteroneMeSH, HMDB
5 beta Pregnane 3,20 dioneMeSH, HMDB
5 beta-Pregnane-3,20-dioneMeSH, HMDB
5-beta-DihydroprogesteroneMeSH, HMDB
5alpha-DHPMeSH, HMDB
3,20-Allopregnanedione, (5beta,13alpha,17alpha)-isomerMeSH, HMDB
5 alpha PregnanedioneMeSH, HMDB
5alpha DHPMeSH, HMDB
5alpha Pregnane 3,20 dioneMeSH, HMDB
5beta DHPMeSH, HMDB
5beta-DHPMeSH, HMDB
3,20 AllopregnanedioneMeSH, HMDB
3,20-Allopregnanedione, (5alpha)-isomerMeSH, HMDB
5 alpha Pregnane 3,20 dioneMeSH, HMDB
5 alpha-DihydroprogesteroneMeSH, HMDB
5 alpha-Pregnane-3,20-dioneMeSH, HMDB
5 beta DihydroprogesteroneMeSH, HMDB
5-alpha-PregnanedioneMeSH, HMDB
Chemical FormulaC21H32O2
Average Molecular Weight316.4776
Monoisotopic Molecular Weight316.240230268
IUPAC Name(1S,2S,7S,10R,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
Traditional Name5a-pregnane-3,20-dione
CAS Registry Number566-65-4
SMILES
[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])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/h14,16-19H,4-12H2,1-3H3/t14-,16-,17+,18-,19-,20-,21+/m0/s1
InChI KeyXMRPGKVKISIQBV-BJMCWZGWSA-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-oxosteroid
  • 3-oxo-5-alpha-steroid
  • Oxosteroid
  • 3-oxosteroid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point200 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.06ALOGPS
logP4.19ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)19.34ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity91.88 m³·mol⁻¹ChemAxon
Polarizability37.86 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0umu-9810000000-76ef4cf96a30792f4d73View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0umu-9810000000-7151501afadd028a99ecView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0umu-9810000000-76ef4cf96a30792f4d73View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0umu-9810000000-7151501afadd028a99ecView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f76-4910000000-81546b52d59f9518cb0cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f76-4910000000-dbf8c4ca357b5f19f54dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fkj-0391000000-1964b2faffc1ae5ab9b4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0159000000-fdffc096796499edd3d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05p2-0492000000-3f8a5badfddf1ced4edfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-2590000000-932901e825351ef60bc4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-8848319d0e10bc22bc8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0039000000-04efc7afcedbf957d0eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006t-1090000000-259e4f493b06ea76a0d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0069000000-c9fab448f80ee78066daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0491000000-c1e83a8609698882ba42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-3920000000-1083c653754015836eb2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-be6e06313d0abca8e664View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0049000000-e44dad0db5aa758e4dd5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ls-0091000000-f15b1c3e520b40f7172bView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Fibroblasts
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0003759
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023222
KNApSAcK IDNot Available
Chemspider ID83782
KEGG Compound IDC03681
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link5%CE%B1-Dihydroprogesterone
METLIN IDNot Available
PubChem Compound92810
PDB IDNot Available
ChEBI ID28952
References
Synthesis ReferenceValenta, Zdenek. Steroid total synthesis and intermediates. U.S. (1975), 14 pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available