Record Information
Version1.0
Creation date2010-04-08 22:05:09 UTC
Update date2019-11-26 02:56:42 UTC
Primary IDFDB001871
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameProgesterone
DescriptionProgesterone, also known as gesterol or crinone, 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, progesterone is considered to be a steroid lipid molecule. Progesterone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Progesterone is a potentially toxic compound.
CAS Number57-83-0
Structure
Thumb
Synonyms
SynonymSource
(S)-4-Pregnene-3,20-dioneChEBI
(S)-Pregn-4-en-3,20-dioneChEBI
(S)-ProgesteroneChEBI
17alpha-ProgesteroneChEBI
4-Pregnene-3,20-dioneChEBI
AgolutinChEBI
AkrolutinChEBI
Corpus luteum hormoneChEBI
CrinoneChEBI
Delta(4)-Pregnene-3,20-dioneChEBI
GelbkoerperhormonChEBI
LuteohormoneChEBI
ProgesteronChEBI
PrometriumKegg
17a-ProgesteroneGenerator
17Α-progesteroneGenerator
Δ(4)-pregnene-3,20-dioneGenerator
3,20-Pregnene-4HMDB
4-Pregnen-3,20-dioneHMDB
beta-ProgesteroneHMDB
Bio-lutonHMDB
CIDRHMDB
ColprosteroneHMDB
CorlutinHMDB
CorlutinaHMDB
CorluviteHMDB
CorporinHMDB
Crinone progesterone gelHMDB
CurretabHMDB
CyclogestHMDB
CyclogesterinHMDB
D4-Pregnene-3,20-dioneHMDB
DelalutinHMDB
DuraprogenHMDB
EstimaHMDB
FlavolutanHMDB
FologenonHMDB
GesterolHMDB
Gesterol 100HMDB
Gesterol 50HMDB
GestironHMDB
GestoneHMDB
GestormoneHMDB
GestronHMDB
GlanducorpinHMDB
GynlutinHMDB
GynolutonHMDB
GynolutoneHMDB
HormoflaveineHMDB
HormolutonHMDB
Hydroxyprogesterone caproateHMDB
Hydroxyprogesterone caproic acidHMDB
LingusorbsHMDB
Lipo-lutinHMDB
LucorteumHMDB
Lucorteum solHMDB
LugesteronHMDB
Luteal hormoneHMDB
Luteocrin normaleHMDB
LuteodynHMDB
LuteoganHMDB
LuteolHMDB
LuteopurHMDB
LuteosanHMDB
LuteostabHMDB
LuteovisHMDB
LuteumHMDB
LutexHMDB
LutidonHMDB
LutociclinaHMDB
Lutocuclin mHMDB
LutocyclinHMDB
Lutocyclin mHMDB
LutocylinHMDB
LutocylolHMDB
LutoformHMDB
LutogylHMDB
LutrenHMDB
LutromoneHMDB
MembrettesHMDB
MethylpregnoneHMDB
MPAHMDB
NalutronHMDB
PercutacrineHMDB
Percutacrine luteiniqueHMDB
PiapononHMDB
PranoneHMDB
Pregn-4-en-3,20-dioneHMDB
Pregn-4-ene-3,20-dioneHMDB
Pregnene-3,20-dioneHMDB
PregnenedioneHMDB
PrimolutHMDB
ProchieveHMDB
ProgeffikHMDB
ProgekanHMDB
ProgestanHMDB
ProgestasertHMDB
ProgesterolHMDB
ProgesteronumHMDB
ProgestinHMDB
ProgestogelHMDB
ProgestolHMDB
ProgestonHMDB
ProgestoneHMDB
ProgestosolHMDB
ProgestronHMDB
ProgestronolHMDB
ProjestajectHMDB
ProletsHMDB
ProlidonHMDB
ProlutinHMDB
ProlutonHMDB
ProlutoneHMDB
ProntogestHMDB
ProtormoneHMDB
SyngesteroneHMDB
SyngestretsHMDB
Synovex SHMDB
SyntolutanHMDB
UtrogestHMDB
UtrogestanHMDB
VitarrineHMDB
Progesterone, (13 alpha,17 alpha)-(+-)-isomerHMDB
Progesterone, (17 alpha)-isomerHMDB
Progesterone, (9 beta,10 alpha)-isomerHMDB
17alpha-progesteronemanual
Progesteronemanual
Predicted Properties
PropertyValueSource
Water Solubility0.0055 g/LALOGPS
logP3.58ALOGPS
logP4.15ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)18.92ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity92.71 m³·mol⁻¹ChemAxon
Polarizability37.26 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H30O2
IUPAC name(1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
InChI IdentifierInChI=1S/C21H30O2/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/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1
InChI KeyRJKFOVLPORLFTN-LEKSSAKUSA-N
Isomeric SMILES[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
Average Molecular Weight314.4617
Monoisotopic Molecular Weight314.224580204
Classification
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
  • Oxosteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point121 oC
Boiling PointNot Available
Experimental Water Solubility0.00881 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP3.87HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
Charge0
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-006x-7931000000-f6ad83adccd7e016fa29Spectrum
GC-MSProgesterone, non-derivatized, GC-MS Spectrumsplash10-0fbc-5910000000-422e38df6de7e8b0a4b7Spectrum
GC-MSProgesterone, non-derivatized, GC-MS Spectrumsplash10-0fbc-5910000000-385f45345742235da8e0Spectrum
GC-MSProgesterone, non-derivatized, GC-MS Spectrumsplash10-024l-6923000000-639c7405f69825de7f90Spectrum
GC-MSProgesterone, non-derivatized, GC-MS Spectrumsplash10-0229-2941000000-1e075d8489b79cf4e34aSpectrum
GC-MSProgesterone, non-derivatized, GC-MS Spectrumsplash10-0229-3963000000-f35e3d9faf6b2ee87465Spectrum
GC-MSProgesterone, non-derivatized, GC-MS Spectrumsplash10-0fbc-5910000000-422e38df6de7e8b0a4b7Spectrum
GC-MSProgesterone, non-derivatized, GC-MS Spectrumsplash10-0fbc-5910000000-385f45345742235da8e0Spectrum
GC-MSProgesterone, non-derivatized, GC-MS Spectrumsplash10-0f6x-2910000000-1baafb91a3e0b988caa7Spectrum
Predicted GC-MSProgesterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000g-1590000000-3ebb52b90c541e38c0b4Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-1009000000-0f8b7c3e6c2265c3889fSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052b-8900000000-0b0167121b798e7e7534Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052b-9400000000-881510cbcecd9cb61f4fSpectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positivesplash10-024l-6923000000-639c7405f69825de7f90Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positivesplash10-0229-2941000000-1e075d8489b79cf4e34aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-004i-0950000000-ca28d8dfdf780c201716Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000i-1900000000-857f6720dd17fb2547d1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-004i-3930000000-fda87095285a83b85ad5Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kb-7955000000-a22f06eac940cd4f753dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0139000000-6b47f75a44df3e20fa3bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0aba-0950000000-b26d04d179294aa67cc7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0aba-0920000000-d0a3365efe1f8a589564Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-05aj-0910000000-61d7a07e6be85600e1f1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0009000000-67c6f0147801f0ece957Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-05mk-8956000000-aa5fe992c41261b62fbfSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-052b-6910000000-5e26497eb2d0150a30acSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4j-8900000000-7ca6fd15f0ccc18bfa31Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-052b-9700000000-523fe1ad11bfcbb46f85Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-054k-9400000000-e3d581bd8685e1d3f35dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0269000000-9aa25f8d44bc44ee4d4cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06dj-0491000000-c312ac322a549be24facSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbc-2290000000-859101eb546be9ddc938Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0019000000-e021f799bd2d232a0592Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0049000000-55066424591bf87a4a49Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-1090000000-e9387b8ab692f5ef9083Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC00410
Pubchem Compound ID5994
Pubchem Substance IDNot Available
ChEBI ID17026
Phenol-Explorer IDNot Available
DrugBank IDDB00396
HMDB IDHMDB01830
CRC / DFC (Dictionary of Food Compounds) IDHLF54-N:HLF54-N
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34898
KNApSAcK IDC00034649
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDProgesterone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.