Showing metabocard for 16-Dehydroprogesterone (BMDB0000995)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:39:38 UTC
Update Date2020-04-22 15:06:15 UTC
BMDB IDBMDB0000995
Secondary Accession Numbers
  • BMDB00995
Metabolite Identification
Common Name16-Dehydroprogesterone
Description16-Dehydroprogesterone, also known as delta.16-progesterone, 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. Thus, 16-dehydroprogesterone is considered to be a steroid. Based on a literature review a small amount of articles have been published on 16-Dehydroprogesterone.
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 Weight312.4458
Monoisotopic Molecular Weight312.20893014
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
CAS Registry Number1096-38-4
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 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/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
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 Point185 - 187 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007k-0790000000-587e2010759d04be79daView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0009000000-70101cfe59fde51a8ff9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4j-5900000000-8c5e3f1358c9efe68931View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4j-9500000000-1fa651a1bfd23c37c15bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0179000000-67a5fd6afc1237e6f0c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01vt-0391000000-73037a7fa24c2f096328View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7a-2490000000-162c2aa3fd60d3279a3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0019000000-f49571271662f7a5da14View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-0098000000-4d72f69ebbb13d5f7c4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gbd-0090000000-4cd4d8acb44933c4d831View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0029000000-753e4d201cfb7cc7b807View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ow-1493000000-67e624229aa746721027View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-7920000000-6f3d42fcb774cf571fa5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-152b659b4891e36b54f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0049000000-4d4a6f7ba007f9c34c62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07fu-0192000000-c9494d220d3973cd4385View in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000995
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022357
KNApSAcK IDNot Available
Chemspider ID92118
KEGG Compound IDC03207
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5926
PubChem Compound101964
PDB IDNot Available
ChEBI ID18204
References
Synthesis ReferenceJohnson, William S. Intermediates in total synthesis of 16-dehydroprogesterone. U.S. (1973), 15 pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available