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Human Metabolome Database Version 3.5

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Showing metabocard for 16-Dehydroprogesterone (HMDB00995)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:43 -0700
HMDB ID HMDB00995
Secondary Accession Numbers None
Metabolite Identification
Common Name 16-Dehydroprogesterone
Description Prometrium is a brand of micronized progesterone. It is used as a prescription drug in hormone replacement therapy.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 16,17-Didehydroprogesterone
  2. 16-Dehydroprogesterone
  3. 3,20-Dioxopregna-4,16-diene
  4. 4,16-Pregnadiene-3,20-dione
  5. D16-Progesterone
  6. D4,16-Pregnadiene-3,20-dione
  7. delta.16-Progesterone
  8. Delta4,16-Pregnadiene-3,20-dione
  9. Pregna-4,16-diene-3,20-dione
Chemical Formula C21H28O2
Average Molecular Weight 312.4458
Monoisotopic Molecular Weight 312.20893014
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 IUPAC Name 16-dehydroprogesterone
CAS Registry Number 1096-38-4
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 Key VRRHHTISESGZFN-RKFFNLMFSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Gluco/mineralocorticoids, Progestogins and Derivatives
Other Descriptors
  • 20-oxo steroid(ChEBI)
  • 3-oxo Delta(4)-steroid(ChEBI)
  • Aliphatic Homopolycyclic Compounds
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives(Lipidmaps)
  • enone(ChEBI)
Substituents
  • 20 Keto Steroid
  • 3 Keto Steroid
  • Cyclohexane
  • Cyclohexene
  • Decaline
  • Ketone
Direct Parent Gluco/mineralocorticoids, Progestogins and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 185 - 187 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0097 g/L ALOGPS
LogP 3.80 ALOGPS
LogP 4 ChemAxon
LogS -4.51 ALOGPS
pKa (strongest acidic) 18.98 ChemAxon
pKa (strongest basic) -4.6 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 34.14 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 93.58 ChemAxon
Polarizability 36.77 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022357
KNApSAcK ID Not Available
Chemspider ID 92118 Link_out
KEGG Compound ID C03207 Link_out
BioCyc ID 16-17-DIDEHYDROPROGESTERONE Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00995 Link_out
Metagene Link HMDB00995 Link_out
METLIN ID 5926 Link_out
PubChem Compound 101964 Link_out
PDB ID Not Available
ChEBI ID 18204 Link_out
References
Synthesis Reference Johnson, William S. Intermediates in total synthesis of 16-dehydroprogesterone. U.S. (1973), 15 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Schindler AE, Wuchter J: Studies on steroids in urine of the male newborn. Biol Neonate. 1975;27(3-4):192-207. Pubmed: 126703 Link_out