Showing Compound 21-Deoxycortisol (FDB023283)

Record Information

Version

1.0

Creation date

2011-09-21 00:27:26 UTC

Update date

2015-07-21 06:57:37 UTC

Primary ID

FDB023283

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

21-Deoxycortisol

Description

Plasma 21-deoxycortisol (21DF) is an excellent marker of 21-hydroxylase deficiency. Currently, it is the only marker able to detect heterozygous carriers with 21-hydroxylase deficiency after Adrenocorticotropic Hormone (ACTH) stimulation. The syndrome of congenital adrenal hyperplasia (CAH) comprises the spectrum of autosomal recessive enzymatic disorders that impair cortisol biosynthesis. The hormonal pattern and clinical manifestations result from hyperstimulation of the adrenal cortex by excessive production of ACTH, untied from the negative feedback exerted by reduced cortisol levels, and the ultimate accumulation of F precursors and androgens. These abnormalities predispose the female newborn to ambiguous genitalia (female pseudohermaphroditism) and precocious puberty that may occur in both sexes. CAH due to 21-hydroxylase deficiency (21OHD) comprises nearly 90% of all cases, with an estimated worldwide incidence of 1 in 14,000 live births. Because 21-deoxycortisol (21DF) is an 11b-hydroxylase (11bOH) derivative of 17-hydroxyprogesterone (17OHP), its serum levels are parallel and proportionally elevated in patients with 21OHD but decreased or undetectable in those with 11b-hydroxylase deficiency (11bOHD). Due to the marked buildup of 17OHP in 21OHD, this precursor steroid can proceed directly to 11-hydroxylation, producing distinct elevations of 21DF. (PMID: 16551734, 10731638) [HMDB]

CAS Number

641-77-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
11b,17-Dihydroxy-pregn-4-ene-3,20-dione	HMDB
11b,17-dihydroxy-Pregn-4-ene-3,20-dione	hmdb
11b,17-Dihydroxy-progesterone	HMDB
11b,17-dihydroxy-Progesterone	hmdb
11b,17a-Dihydroxypregn-4-ene-3,20-dione	HMDB
11b,17a-Dihydroxyprogesterone	HMDB
21-Dehydrohydrocortisone	HMDB
21-Deoxycortisol	hmdb
21-Deoxyhydrocortisone	HMDB
21-Desoxycortisol	HMDB

Showing 1 to 10 of 12 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.06 g/L	ALOGPS
logP	2.29	ALOGPS
logP	2.09	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	12.69	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	95.7 m³·mol⁻¹	ChemAxon
Polarizability	38.59 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C21H30O4

IUPAC name

(1S,2R,10S,11S,14R,15S,17R)-14-acetyl-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

InChI Identifier

InChI=1S/C21H30O4/c1-12(22)21(25)9-7-16-15-5-4-13-10-14(23)6-8-19(13,2)18(15)17(24)11-20(16,21)3/h10,15-18,24-25H,4-9,11H2,1-3H3/t15-,16-,17+,18+,19-,20-,21-/m0/s1

InChI Key

LCZBQMKVFQNSJR-CZUPSRJTSA-N

Isomeric SMILES

[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)C[C@@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

Average Molecular Weight

346.4605

Monoisotopic Molecular Weight

346.214409448

Classification

Description

Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-oxosteroid
3-oxo-delta-4-steroid
3-oxosteroid
Hydroxysteroid
Oxosteroid
11-alpha-hydroxysteroid
11-hydroxysteroid
17-hydroxysteroid
Delta-4-steroid
Cyclohexenone
Tertiary alcohol
Alpha-hydroxy ketone
Cyclic alcohol
Secondary alcohol
Ketone
Cyclic ketone
Organic oxide
Organooxygen compound
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect:

Health condition:

Metabolism and nutrition disorders:

Observation:

Preterm birth

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Hepatic tissue

Organ and components:

Testicle

Endocrine gland:

Adrenal gland

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

System process:

Reproduction

Cellular process:

Cell signaling

Role

Biological role:

Molecular messenger:

Industrial application:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	21-Deoxycortisol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05mo-2957000000-d023e738b8e5b9a63cd2	Spectrum
Predicted GC-MS	21-Deoxycortisol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-2116900000-05061eac5c0a64618c6f	Spectrum
Predicted GC-MS	21-Deoxycortisol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004j-0009000000-71aa430e3e20af8b2c95	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01t9-0259000000-2fb2818f214612a10bbf	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4u-2690000000-3dd37cf0a48974795770	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-2d39ebc543dfc8393535	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f9b-0029000000-17d7de8bb31c25cb6a4a	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kp0-1096000000-a21e11412ea47ba1ded2	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0009000000-19287cb485f1fddca890	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0009000000-d1621dd0a863681c08e9	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udr-0079000000-0ce5cfb77bffcbe17979	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0009000000-f6d8370e2ec523e5bab7	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1924000000-3c950cee78e9c59f06f0	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06tf-7960000000-15e137fe577c2459aaf6	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

193458

ChEMBL ID

Not Available

KEGG Compound ID

C05497

Pubchem Compound ID

222803

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB04030

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Anatidae	Expected but not quantified	Not Available	HMDB
Beefalo	Expected but not quantified	Not Available	HMDB
Bison	Expected but not quantified	Not Available	HMDB
Buffalo	Expected but not quantified	Not Available	HMDB
Cattle (Beef, Veal)	Expected but not quantified	Not Available	HMDB
Chicken	Expected but not quantified	Not Available	HMDB
Columbidae (Dove, Pigeon)	Expected but not quantified	Not Available	HMDB
Deer	Expected but not quantified	Not Available	HMDB
Domestic goat	Expected but not quantified	Not Available	HMDB
Domestic pig	Expected but not quantified	Not Available	HMDB