Human Metabolome Database Version 3.5

Showing metabocard for 11b-Hydroxyandrost-4-ene-3,17-dione (HMDB06773)

Record Information
Version 3.5
Creation Date 2008-08-08 04:29:51 -0600
Update Date 2013-02-08 17:15:18 -0700
HMDB ID HMDB06773
Secondary Accession Numbers None
Metabolite Identification
Common Name 11b-Hydroxyandrost-4-ene-3,17-dione
Description 11beta-Hydroxyandrost-4-ene-3,17-dione is an intermediate in adrenosterone production. 11beta-Hydroxyandrost-4-ene-3,17-dione is produced from androst-4-ene-3,17-dione, a reaction catalyzed by the enzyme cytochrome P450 B [EC:1.14.15.4]. 11beta-Hydroxyandrost-4-ene-3,17-dione is then converted into adrenosterone by the enzyme 11beta-hydroxysteroid dehydrogenase [EC:1.1.1.146].
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 11beta-Hydroxyandrost-4-ene-3,17-dione
  2. 4-Androsten-11beta-ol-3,17-dione
  3. Androst-4-ene-3,17-dione-11beta-ol
Chemical Formula C19H26O3
Average Molecular Weight 302.4079
Monoisotopic Molecular Weight 302.188194698
IUPAC Name (1S,2R,10S,11S,15S,17S)-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione
Traditional IUPAC Name (1S,2R,10S,11S,15S,17S)-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione
CAS Registry Number 382-44-5
SMILES [H][C@@]12CCC(=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier InChI=1S/C19H26O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-15,17,21H,3-8,10H2,1-2H3/t13-,14-,15-,17+,18-,19-/m0/s1
InChI Key WSCUHXPGYUMQEX-KCZNZURUSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Androgens and Derivatives
Other Descriptors
  • 11beta-hydroxy steroid(ChEBI)
  • 17-oxo steroid(ChEBI)
  • 3-oxo steroid(ChEBI)
  • Aliphatic Homopolycyclic Compounds
  • C19 steroids (androgens) and derivatives(KEGG)
  • C19 steroids (androgens) and derivatives(Lipidmaps)
  • Hydroxysteroids
  • Ketosteroids
  • androstanoid(ChEBI)
Substituents
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Decaline
  • Ketone
  • Secondary Alcohol
  • Sesquiterpene Backbone
Direct Parent Androgens 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 0.082 g/L ALOGPS
LogP 2.00 ALOGPS
LogP 2.62 ChemAxon
LogS -3.57 ALOGPS
pKa (strongest acidic) 14.88 ChemAxon
pKa (strongest basic) -2.9 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 54.37 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 85.2 ChemAxon
Polarizability 34 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
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
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB024075
KNApSAcK ID Not Available
Chemspider ID 84958 Link_out
KEGG Compound ID C05284 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06773 Link_out
Metagene Link HMDB06773 Link_out
METLIN ID Not Available
PubChem Compound 94141 Link_out
PDB ID Not Available
ChEBI ID 27967 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References Not Available

Enzymes
Name: Cytochrome P450 11B1, mitochondrial
Reactions:
Reduced adrenal ferredoxin + Androstenedione + Oxygen unknown 11b-Hydroxyandrost-4-ene-3,17-dione + Oxidized adrenal ferredoxin + Water details
Gene Name: CYP11B1
Uniprot ID: P15538 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Estradiol 17-beta-dehydrogenase 2
Reactions:
11beta,17beta-Dihydroxy-4-androsten-3-one + NAD unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADH + Hydrogen Ion details
11beta,17beta-Dihydroxy-4-androsten-3-one + NADP unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADPH + Hydrogen Ion details
Gene Name: HSD17B2
Uniprot ID: P37059 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Estradiol 17-beta-dehydrogenase 8
Reactions:
11beta,17beta-Dihydroxy-4-androsten-3-one + NAD unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADH + Hydrogen Ion details
11beta,17beta-Dihydroxy-4-androsten-3-one + NADP unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADPH + Hydrogen Ion details
Gene Name: HSD17B8
Uniprot ID: Q92506 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:
11b-Hydroxyandrost-4-ene-3,17-dione + NADP unknown Adrenosterone + NADPH + Hydrogen Ion details
Gene Name: HSD11B1
Uniprot ID: P28845 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Estradiol 17-beta-dehydrogenase 1
Reactions:
11beta,17beta-Dihydroxy-4-androsten-3-one + NAD unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADH + Hydrogen Ion details
11beta,17beta-Dihydroxy-4-androsten-3-one + NADP unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADPH + Hydrogen Ion details
Gene Name: HSD17B1
Uniprot ID: P14061 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 3-keto-steroid reductase
Reactions:
11beta,17beta-Dihydroxy-4-androsten-3-one + NAD unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADH + Hydrogen Ion details
11beta,17beta-Dihydroxy-4-androsten-3-one + NADP unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADPH + Hydrogen Ion details
Gene Name: HSD17B7
Uniprot ID: P56937 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 17-beta-hydroxysteroid dehydrogenase type 6
Reactions:
11beta,17beta-Dihydroxy-4-androsten-3-one + NAD unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADH + Hydrogen Ion details
11beta,17beta-Dihydroxy-4-androsten-3-one + NADP unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADPH + Hydrogen Ion details
Gene Name: HSD17B6
Uniprot ID: O14756 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 11B2, mitochondrial
Reactions:
Reduced adrenal ferredoxin + Androstenedione + Oxygen unknown 11b-Hydroxyandrost-4-ene-3,17-dione + Oxidized adrenal ferredoxin + Water details
Gene Name: CYP11B2
Uniprot ID: P19099 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Estradiol 17-beta-dehydrogenase 12
Reactions:
11beta,17beta-Dihydroxy-4-androsten-3-one + NAD unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADH + Hydrogen Ion details
11beta,17beta-Dihydroxy-4-androsten-3-one + NADP unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADPH + Hydrogen Ion details
Gene Name: HSD17B12
Uniprot ID: Q53GQ0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA