Human Metabolome Database Version 3.5

Showing metabocard for 3a,21-Dihydroxy-5b-pregnane-11,20-dione (HMDB06755)

Record Information
Version 3.5
Creation Date 2008-08-06 05:12:18 -0600
Update Date 2013-05-13 15:49:19 -0600
HMDB ID HMDB06755
Secondary Accession Numbers None
Metabolite Identification
Common Name 3a,21-Dihydroxy-5b-pregnane-11,20-dione
Description 3alpha,21-Dihydroxy-5beta-pregnane-11,20-dione is an intermediate in C21-Steroid hormone metabolism. 3alpha,21-Dihydroxy-5beta-pregnane-11,20-dione is converted from Tetrahydrocorticosterone via the enzyme 11beta-hydroxysteroid dehydrogenase (EC 1.1.1.146). It is then converted to 3alpha,20alpha,21-Trihydroxy-5beta-pregnane-11-one via the enzyme 3alpha(or 20beta)-hydroxysteroid dehydrogenase (EC 1.1.1.53).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3alpha,21-Dihydroxy-5beta-pregnane-11,20-dione
  2. 5beta-Pregnane-3alpha,21-diol-11,20-dione
Chemical Formula C21H32O4
Average Molecular Weight 348.4764
Monoisotopic Molecular Weight 348.230059512
IUPAC Name (1S,2S,5R,7R,10S,11S,15S)-5-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-17-one
Traditional IUPAC Name (1S,2S,5R,7R,10S,11S,15S)-5-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-17-one
CAS Registry Number 566-03-0
SMILES [H][C@@]12CCC(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C
InChI Identifier InChI=1S/C21H32O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h12-16,19,22-23H,3-11H2,1-2H3/t12-,13-,14+,15+,16?,19-,20+,21+/m1/s1
InChI Key XWYBFXIUISNTQG-XPYNSANSSA-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
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives(Lipidmaps)
Substituents
  • 11 Keto Steroid
  • 20 Keto Steroid
  • 3 Hydroxy Steroid
  • Alpha Ketoaldehyde
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Decaline
  • Ketone
  • Primary Alcohol
  • 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 0.064 g/L ALOGPS
LogP 2.56 ALOGPS
LogP 2.25 ChemAxon
LogS -3.74 ALOGPS
pKa (strongest acidic) 13.86 ChemAxon
pKa (strongest basic) -1.4 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 74.6 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 95.28 ChemAxon
Polarizability 39.15 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Steroidogenesis SMP00130 map00140 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB024059
KNApSAcK ID Not Available
Chemspider ID 24850110 Link_out
KEGG Compound ID C05478 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06755 Link_out
Metagene Link HMDB06755 Link_out
METLIN ID Not Available
PubChem Compound 44263347 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

Enzymes
Name: Aldo-keto reductase family 1 member C4
Reactions:
3a,21-Dihydroxy-5b-pregnane-11,20-dione + NAD unknown 21-Hydroxy-5b-pregnane-3,11,20-trione + NADH + Hydrogen Ion details
3a,21-Dihydroxy-5b-pregnane-11,20-dione + NADP unknown 21-Hydroxy-5b-pregnane-3,11,20-trione + NADPH + Hydrogen Ion details
Gene Name: AKR1C4
Uniprot ID: P17516 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Corticosteroid 11-beta-dehydrogenase isozyme 2
Reactions: Not Available
Gene Name: HSD11B2
Uniprot ID: P80365 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Corticosteroid 11-beta-dehydrogenase isozyme 1
Reactions:
Tetrahydrocorticosterone + NADP unknown 3a,21-Dihydroxy-5b-pregnane-11,20-dione + NADPH + Hydrogen Ion details
Gene Name: HSD11B1
Uniprot ID: P28845 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA