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Showing metabocard for 11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid (HMDB11652)

Record Information
Version 3.5
Creation Date 2009-02-03 03:00:23 -0700
Update Date 2013-02-08 17:27:03 -0700
HMDB ID HMDB11652
Secondary Accession Numbers None
Metabolite Identification
Common Name 11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid
Description 11b-hydroxy-3,20-dioxopregn-4-en-21-oic acid or HDOPA is a major metabolite of corticosterone that is typically elevated in the liver. The in vivo conversion of corticosterone to DHOPA and then to HDOPA is thought to proceed via the aldehyde intermediate 11b-hydroxy-3,20-dioxopregn-4-en-21-al. Cytochrome P450 3A4 (CYP3A4), is known to convert corticosterone to the gem-diol form of the aldehyde. Because CYP3A4 is highly abundant in the liver, the conversion of corticosterone to its aldehyde presumably occurs readily, and the formation of DHOPA by isomerization of the aldehyde. Subsequent dehydrogenation of DHOPA to HDOPA may be done by one of several liver specfici dehydrogenases. Possible candidates include aldehyde dehydrogenase type 3, lactate dehydrogenase A4, or 11b-hydroxysteroid dehydrogenase I. HDOPA has also been identified as a biomarker that is elevated (3700 X) in animals that have been treated with PPARalpha agonists. Peroxisome proliferator-activated receptor alpha (PPARalpha) is a nuclear receptor with manifold effects on intermediary metabolism (PMID: 17550978 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 11beta-Hydroxy-3,20-dioxopregn-4-en-21-oate
  2. 11beta-Hydroxy-3,20-dioxopregn-4-en-21-oic acid
  3. HDOPA
Chemical Formula C22H32O5
Average Molecular Weight 376.4865
Monoisotopic Molecular Weight 376.224974134
IUPAC Name 3-hydroxy-3-[(2R,15S,17S)-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]propanoic acid
Traditional IUPAC Name 3-hydroxy-3-[(2R,15S,17S)-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]propanoic acid
CAS Registry Number Not Available
SMILES C[C@]12C[C@H](O)C3C(CCC4=CC(=O)CC[C@]34C)C1CCC2C(O)CC(O)=O
InChI Identifier InChI=1S/C22H32O5/c1-21-8-7-13(23)9-12(21)3-4-14-15-5-6-16(17(24)10-19(26)27)22(15,2)11-18(25)20(14)21/h9,14-18,20,24-25H,3-8,10-11H2,1-2H3,(H,26,27)/t14?,15?,16?,17?,18-,20?,21-,22-/m0/s1
InChI Key MSUMOHDXPKCNSB-ZUNXIJJCSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Gluco/mineralocorticoids, Progestogins and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
Substituents
  • 11 Hydroxy Steroid
  • 3 Keto Steroid
  • Beta Hydroxy Acid
  • Carboxylic Acid
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Decaline
  • Ketone
  • Secondary Alcohol
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
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available 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 0.06 g/L ALOGPS
LogP 1.67 ALOGPS
LogP 1.99 ChemAxon
LogS -3.80 ALOGPS
pKa (strongest acidic) 4.37 ChemAxon
pKa (strongest basic) -0.28 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 94.83 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 101.36 ChemAxon
Polarizability 41.66 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 FDB028343
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB11652 Link_out
Metagene Link HMDB11652 Link_out
METLIN ID Not Available
PubChem Compound 53481012 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available