Record Information
Version1.0
Creation date2011-09-21 00:27:26 UTC
Update date2015-07-21 06:57:37 UTC
Primary IDFDB023283
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name21-Deoxycortisol
DescriptionPlasma 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 Number641-77-0
Structure
Thumb
Synonyms
SynonymSource
11b,17-Dihydroxy-pregn-4-ene-3,20-dioneHMDB
11b,17-Dihydroxy-progesteroneHMDB
11b,17a-Dihydroxypregn-4-ene-3,20-dioneHMDB
11b,17a-DihydroxyprogesteroneHMDB
21-DehydrohydrocortisoneHMDB
21-DeoxyhydrocortisoneHMDB
21-DesoxycortisolHMDB
4-Pregnene-11beta,17alpha-diol-3,20-dioneHMDB
Pregn-4-ene-11b,17a-diol-3,20-dioneHMDB
11b,17-dihydroxy-Pregn-4-ene-3,20-dionehmdb
11b,17-dihydroxy-Progesteronehmdb
21-Deoxycortisolhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.06 g/LALOGPS
logP2.29ALOGPS
logP2.09ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)12.69ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity95.7 m³·mol⁻¹ChemAxon
Polarizability38.59 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H30O4
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 IdentifierInChI=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 KeyLCZBQMKVFQNSJR-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 Weight346.4605
Monoisotopic Molecular Weight346.214409448
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/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 FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05mo-2957000000-d023e738b8e5b9a63cd2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-2116900000-05061eac5c0a64618c6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0009000000-71aa430e3e20af8b2c95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-0259000000-2fb2818f214612a10bbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4u-2690000000-3dd37cf0a48974795770View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-2d39ebc543dfc8393535View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f9b-0029000000-17d7de8bb31c25cb6a4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kp0-1096000000-a21e11412ea47ba1ded2View in MoNA
ChemSpider ID193458
ChEMBL IDNot Available
KEGG Compound IDC05497
Pubchem Compound ID222803
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04030
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Cytochrome P450, family 21, subfamily A, polypeptide 2CYP21A2Q08AG9
Cytochrome P450 21-hydroxylaseP450-CYP21BQ16874
Pathways
NameSMPDB LinkKEGG Link
SteroidogenesisSMP00130 map00140
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference