Human Metabolome Database Version 3.5

Showing metabocard for 11b,17a,21-Trihydroxypreg-nenolone (HMDB06760)

Record Information
Version 3.5
Creation Date 2008-08-06 09:19:57 -0600
Update Date 2013-02-08 17:15:16 -0700
HMDB ID HMDB06760
Secondary Accession Numbers
  • HMDB06761
Metabolite Identification
Common Name 11b,17a,21-Trihydroxypreg-nenolone
Description 11beta,17alpha,21-Trihydroxypregnenolone is an intermediate in C21-Steroid hormone metabolism. 11beta,17alpha,21-Trihydroxypregnenolone is the 4th to last step in the synthesis of Cortol and is converted from 17alpha,21-Dihydroxypregnenolone via the enzyme cytochrome P450 (EC:1.14.15.4). It is then converted to Cortisol via the enzyme 3beta-hydroxy-delta5-steroid dehydrogenase (EC 1.1.1.145) and the enzyme steroid delta-isomerase (EC 5.3.3.1).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 11beta,17alpha,21-Trihydroxypreg-nenolone
  2. 11beta,17alpha,21-Trihydroxypregnenolone
Chemical Formula C21H32O5
Average Molecular Weight 364.4758
Monoisotopic Molecular Weight 364.224974134
IUPAC Name 2-hydroxy-1-[(14R)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one
Traditional IUPAC Name 2-hydroxy-1-[(14R)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethanone
CAS Registry Number Not Available
SMILES CC12CC(O)C3C(CC=C4CC(O)CCC34C)C1CC[C@]2(O)C(=O)CO
InChI Identifier InChI=1S/C21H32O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h3,13-16,18,22-24,26H,4-11H2,1-2H3/t13?,14?,15?,16?,18?,19?,20?,21-/m0/s1
InChI Key HAFVWTUQBYRPOB-QGGNSXJXSA-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
  • 20 Keto Steroid
  • 3 Hydroxy Steroid
  • Alpha Ketoaldehyde
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Ketone
  • Primary Alcohol
  • Secondary Alcohol
  • Tertiary 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 0.54 g/L ALOGPS
LogP 1.38 ALOGPS
LogP 0.71 ChemAxon
LogS -2.83 ALOGPS
pKa (strongest acidic) 12.58 ChemAxon
pKa (strongest basic) -1.4 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 97.99 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 98.45 ChemAxon
Polarizability 40.06 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 FDB024064
KNApSAcK ID Not Available
Chemspider ID 389583 Link_out
KEGG Compound ID C05489 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06760 Link_out
Metagene Link HMDB06760 Link_out
METLIN ID Not Available
PubChem Compound 440708 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: Cytochrome P450 11B1, mitochondrial
Reactions:
17a,21-Dihydroxypreg-nenolone + Reduced ferredoxin + Oxygen unknown 11b,17a,21-Trihydroxypreg-nenolone + Oxidized ferredoxin + Water details
Gene Name: CYP11B1
Uniprot ID: P15538 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1
Reactions:
Hydrocortisone + Hydrogen Ion + NADH unknown 11b,17a,21-Trihydroxypreg-nenolone + NAD details
Gene Name: HSD3B1
Uniprot ID: P14060 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2
Reactions:
Hydrocortisone + Hydrogen Ion + NADH unknown 11b,17a,21-Trihydroxypreg-nenolone + NAD details
Gene Name: HSD3B2
Uniprot ID: P26439 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 11B2, mitochondrial
Reactions:
17a,21-Dihydroxypreg-nenolone + Reduced ferredoxin + Oxygen unknown 11b,17a,21-Trihydroxypreg-nenolone + Oxidized ferredoxin + Water details
Gene Name: CYP11B2
Uniprot ID: P19099 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA