16-Dehydroprogesterone (CHEM035021)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:25:30 UTC
Update Date2016-11-09 01:21:14 UTC
Accession NumberCHEM035021
Identification
Common Name16-Dehydroprogesterone
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,20-Dioxopregna-4,16-dieneChEBI
Delta(4,16)-Pregnadiene-3,20-dioneChEBI
16,17-DidehydroprogesteroneKegg
Δ(4,16)-pregnadiene-3,20-dioneGenerator
4,16-Pregnadiene-3,20-dioneHMDB
D16-ProgesteroneHMDB
D4,16-Pregnadiene-3,20-dioneHMDB
Delta.16-progesteroneHMDB
Delta4,16-Pregnadiene-3,20-dioneHMDB
Pregna-4,16-diene-3,20-dioneHMDB
delta(16)-ProgesteroneHMDB
16-DehydroprogesteroneChEBI
Chemical FormulaC21H28O2
Average Molecular Mass312.446 g/mol
Monoisotopic Mass312.209 g/mol
CAS Registry Number1096-38-4
IUPAC Name(1S,2R,10R,11S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,13-dien-5-one
Traditional Name(1S,2R,10R,11S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,13-dien-5-one
SMILES[H][C@@]12CC=C(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI IdentifierInChI=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/h6,12,16,18-19H,4-5,7-11H2,1-3H3/t16-,18-,19-,20-,21+/m0/s1
InChI KeyVRRHHTISESGZFN-RKFFNLMFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 20-oxosteroids. These are steroid derivatives carrying a C=O group at the 20-position of the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassOxosteroids
Direct Parent20-oxosteroids
Alternative Parents
Substituents
  • 20-oxosteroid
  • Androgen-skeleton
  • Androstane-skeleton
  • 3-oxosteroid
  • Cyclohexenone
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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 Solubility0.0097 g/LALOGPS
logP3.8ALOGPS
logP4ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)18.98ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity93.58 m³·mol⁻¹ChemAxon
Polarizability36.77 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, Positivesplash10-007k-0790000000-587e2010759d04be79daSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0009000000-70101cfe59fde51a8ff9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4j-5900000000-8c5e3f1358c9efe68931Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4j-9500000000-1fa651a1bfd23c37c15bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0179000000-67a5fd6afc1237e6f0c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01vt-0391000000-73037a7fa24c2f096328Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7a-2490000000-162c2aa3fd60d3279a3cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0019000000-f49571271662f7a5da14Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-0098000000-4d72f69ebbb13d5f7c4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gbd-0090000000-4cd4d8acb44933c4d831Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0029000000-753e4d201cfb7cc7b807Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ow-1493000000-67e624229aa746721027Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-7920000000-6f3d42fcb774cf571fa5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-152b659b4891e36b54f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0049000000-4d4a6f7ba007f9c34c62Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07fu-0192000000-c9494d220d3973cd4385Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
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 IDHMDB0000995
FooDB IDFDB022357
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5926
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID92118
ChEBI ID18204
PubChem Compound ID101964
Kegg Compound IDC03207
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Johnson, William S. Intermediates in total synthesis of 16-dehydroprogesterone. U.S. (1973), 15 pp.
2. Schindler AE, Wuchter J: Studies on steroids in urine of the male newborn. Biol Neonate. 1975;27(3-4):192-207.