Human Metabolome Database: Showing metabocard for 11b,21-Dihydroxy-3,20-oxo-5b-pregnan-18-al (HMDB06754)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

enzymes (2) Show 2 proteins

Record Information

Version

3.6

Creation Date

2008-08-06 10:57:16 UTC

Update Date

2017-03-02 21:28:17 UTC

HMDB ID

HMDB06754

Secondary Accession Numbers

None

Metabolite Identification

Common Name

11b,21-Dihydroxy-3,20-oxo-5b-pregnan-18-al

Description

11beta,21-Dihydroxy-3,20-oxo-5beta-pregnan-18-al is an intermediate in C21-Steroid hormone metabolism. 11beta,21-Dihydroxy-3,20-oxo-5beta-pregnan-18-al is converted from Aldosterone via the enzyme 3-oxo-5beta-steroid 4-dehydrogenase (EC:1.3.99.6). It is then converted to 3alpha,11beta,21-Trihydroxy-20-oxo-5beta-pregnan-18-al via the enzyme 3-alpha-hydroxysteroid dehydrogenase (EC:1.1.1.50).

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
11beta,21-Dihydroxy-3,20-oxo-5beta-pregnan-18-al	HMDB
Not available	HMDB

Chemical Formula

C₂₁H₃₂O₅

Average Molecular Weight

364.4758

Monoisotopic Molecular Weight

364.224974134

IUPAC Name

(1S,2S,5R,7R,10S,11S)-5,17-dihydroxy-14-(2-hydroxyacetyl)-2-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-15-carbaldehyde

Traditional Name

(1S,2S,5R,7R,10S,11S)-5,17-dihydroxy-14-(2-hydroxyacetyl)-2-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-15-carbaldehyde

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCC(C(=O)CO)C1(CC(O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C)C=O

InChI Identifier

InChI=1S/C21H32O5/c1-20-7-6-13(24)8-12(20)2-3-14-15-4-5-16(18(26)10-22)21(15,11-23)9-17(25)19(14)20/h11-17,19,22,24-25H,2-10H2,1H3/t12-,13-,14+,15+,16?,17?,19-,20+,21?/m1/s1

InChI Key

YWTDWORQGPLRLL-SXWUTGHTSA-N

Chemical Taxonomy

Classification

Not classified

Ontology

Status

Expected but 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	0.17 mg/mL	ALOGPS
logP	1.69	ALOGPS
logP	0.89	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	13.82	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	96.99 m³·mol^-1	ChemAxon
Polarizability	40.01 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Location

Not Available

Pathways

Name	SMPDB Link	KEGG Link
11-beta-hydroxylase deficiency (CYP11B1)	SMP00575	Not Available
17-alpha-hydroxylase deficiency (CYP17)	SMP00566	Not Available
21-hydroxylase deficiency (CYP21)	SMP00576	Not Available
3-Beta-Hydroxysteroid Dehydrogenase Deficiency	SMP00718	Not Available
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase Deficiency	SMP00373	Not Available
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase Deficiency	SMP00372	Not Available
Apparent mineralocorticoid excess syndrome	SMP00717	Not Available
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH	SMP00371	Not Available
Corticosterone methyl oxidase I deficiency (CMO I)	SMP00577	Not Available
Corticosterone methyl oxidase II deficiency - CMO II	SMP00578	Not Available
Steroidogenesis	SMP00130	map00140

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

DrugBank Metabolite ID

Not Available

Phenol Explorer Compound ID

Not Available

Phenol Explorer Metabolite ID

Not Available

FoodDB ID

FDB024058

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C05473

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

NuGOwiki Link

HMDB06754

Metagene Link

HMDB06754

METLIN ID

Not Available

PubChem Compound

53477896

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

Enzyme Details

1. Aldo-keto reductase family 1 member C4

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:: AKR1C4
Uniprot ID:: P17516
Molecular weight:: 37094.57

Reactions

3a,11b,21-Trihydroxy-20-oxo-5b-pregnan-18-al + NAD → 11b,21-Dihydroxy-3,20-oxo-5b-pregnan-18-al + NADH + Hydrogen Ion	details
3a,11b,21-Trihydroxy-20-oxo-5b-pregnan-18-al + NADP → 11b,21-Dihydroxy-3,20-oxo-5b-pregnan-18-al + NADPH + Hydrogen Ion	details

Enzyme Details

2. 3-oxo-5-beta-steroid 4-dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
Gene Name:: AKR1D1
Uniprot ID:: P51857
Molecular weight:: 32889.38

Reactions

11b,21-Dihydroxy-3,20-oxo-5b-pregnan-18-al + NADP → Aldosterone + NADPH + Hydrogen Ion	details

Showing metabocard for 11b,21-Dihydroxy-3,20-oxo-5b-pregnan-18-al (HMDB06754)

Structure for HMDB06754 (11b,21-Dihydroxy-3,20-oxo-5b-pregnan-18-al)

Enzymes

Reactions

Reactions