Human Metabolome Database Version 3.5

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Showing metabocard for Tetrahydrodeoxycortisol (HMDB05972)

Blood
Urine

Record Information

Version

3.5

Creation Date

2007-04-12 13:06:39 -0600

Update Date

2013-02-08 17:14:26 -0700

HMDB ID

HMDB05972

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Tetrahydrodeoxycortisol

Description

Tetrahydrodeoxycortisol (THS) is a mineralocorticoid, the main urinary metabolite of 11-deoxycortisol. THS excretion is significantly associated with tetrahydroaldosterone excretion, total androgen excretion, and cortisol metabolites. Aldosterone synthesis is highly heritable and is affected by genotype at CYP11B1. Variation in the region of chromosome 8 including the genes steroid 11-beta-hydroxylase (CYP11B1) and aldosterone synthase (CYP11B2) influences mineralocorticoid and glucocorticoid metabolism; differences in 11-hydroxylation efficiency can have downstream effects on mineralocorticoid synthesis. Such effects may be of relevance to the development of low-renin essential hypertension. Genotype differences in CYP11B1 explains approximately 5% of the variance in urinary THS excretion in the population. Excretion of THS is heritable (19.4%) and the T-allele of the -344 C/T polymorphism of CYP11B2 is more strongly associated with higher THS levels than the C-allele. (PMID: 16984984 Link_out

, 15522937 Link_out

, 15272911 Link_out

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

11-Deoxytetrahydrocortisol
3alpha,17alpha,21-Trihydroxy-5beta-pregnan-20-one
5beta-Pregnane-3alpha,17alpha,21-triol-20-one
Tetrahydro-11-deoxycortisol
Tetrahydro-S
Tetrahydrocortexolone

Chemical Formula

C₂₁H₃₄O₄

Average Molecular Weight

350.4923

Monoisotopic Molecular Weight

350.245709576

IUPAC Name

1-[(1S,2S,5R,7R,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-hydroxyethan-1-one

Traditional IUPAC Name

tetrahydrodeoxycortisol

CAS Registry Number

68-60-0

SMILES

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

InChI Identifier

InChI=1S/C21H34O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h13-17,22-23,25H,3-12H2,1-2H3/t13-,14-,15-,16+,17+,19+,20+,21+/m1/s1

InChI Key

UPTAPIKFKZGAGM-FAIYVORSSA-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
Glycine conjugates(Lipidmaps)

Substituents

17 Hydroxy Steroid
20 Keto Steroid
3 Hydroxy Steroid
Alpha Ketoaldehyde
Bicyclohexane
Cyclic Alcohol
Cyclohexane
Decaline
Ketone
Primary Alcohol
Secondary Alcohol
Tertiary Alcohol

Direct Parent

Gluco/mineralocorticoids, Progestogins and Derivatives

Ontology

Status

Detected and Quantified

Origin

Endogenous

Food

Biofunction

Cell signaling
Fuel and energy storage
Fuel or energy source
Hormones, Membrane component
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	0.044 g/L	ALOGPS
LogP	2.49	ALOGPS
LogP	2.42	ChemAxon
LogS	-3.90	ALOGPS
pKa (strongest acidic)	12.59	ChemAxon
pKa (strongest basic)	-1.4	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 A²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	96.01	ChemAxon
Polarizability	40.06	ChemAxon
Formal Charge	0	ChemAxon
Physiological Charge	0	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biofluid Locations

Blood
Urine

Tissue Location

Not Available

Pathways

Not Available

Normal Concentrations

Biofluid	Status	Value	Age	Sex	Condition	Comments
Blood	Expected and not Quantified	Not Applicable	Not Available	Not Available	Normal	Inferred from detection in urine
Urine	Detected and Quantified	0.092 +/- 0.055 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	Not Available
Urine	Detected and Quantified	0.000031 +/- 0.000093 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	Not Available

Abnormal Concentrations

Biofluid	Status	Value	Age	Sex	Condition	Comments
Urine	Detected and Quantified	0.011 +/- 0.0092 umol/mmol creatinine	Adult (>18 years old)	Female	Pregnant with an anencephalic foetus	Not Available
Urine	Detected and Quantified	0.036 +/- 0.024 umol/mmol creatinine	Adult (>18 years old)	Both	Pregnant with a normal foetus	Not Available
Urine	Detected and Quantified	0.022 +/- 0.014 umol/mmol creatinine	Adult (>18 years old)	Female	Thyroid cancer	Not Available
Urine	Detected and Quantified	0.000072 +/- 0.0001 umol/mmol creatinine	Adult (>18 years old)	Female	Stress urinary incontinence	Not Available

Associated Disorders and Diseases

Disease References

Thyroid cancer

Kim KM, Jung BH, Lho DS, Chung WY, Paeng KJ, Chung BC: Alteration of urinary profiles of endogenous steroids and polyunsaturated fatty acids in thyroid cancer. Cancer Lett. 2003 Dec 30;202(2):173-9. Pubmed: 14643447

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

Phenol Explorer Metabolite ID

Not Available

FoodDB ID

FDB023794

KNApSAcK ID