Back to Compounds

Showing Compound Desoxycorticosterol (FDB006404)

Record Information
Version1.0
Creation date2010-04-08 22:07:07 UTC
Update date2018-05-29 00:40:55 UTC
Primary IDFDB006404
Secondary Accession Numbers
  • FDB021873
Chemical Information
FooDB NameDesoxycorticosterol
DescriptionDesoxycorticosterol, also known as 21-hydroxy-4-pregnene-3,20-dione or 21-hydroxyprogesterone, is a member of the class of compounds known as 21-hydroxysteroids. 21-hydroxysteroids are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Thus, desoxycorticosterol is considered to be a steroid lipid molecule. Desoxycorticosterol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Desoxycorticosterol can be synthesized from progesterone. Desoxycorticosterol can also be synthesized into 11-deoxycorticosterone-21-hemisuccinate and 5beta-dihydrodeoxycorticosterone. Desoxycorticosterol can be found in rice, which makes desoxycorticosterol a potential biomarker for the consumption of this food product. Desoxycorticosterol can be found primarily in amniotic fluid and blood, as well as throughout all human tissues. In humans, desoxycorticosterol is involved in the steroidogenesis. Desoxycorticosterol is also involved in several metabolic disorders, some of which include corticosterone methyl oxidase I deficiency (CMO I), 21-hydroxylase deficiency (CYP21), corticosterone methyl oxidase II deficiency - CMO II, and 11-beta-hydroxylase deficiency (CYP11B1). Desoxycorticosterol is a non-carcinogenic (not listed by IARC) potentially toxic compound.
CAS Number64-85-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.017 g/LALOGPS
logP3.1ALOGPS
logP3.33ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)13.86ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.41 m³·mol⁻¹ChemAxon
Polarizability38.19 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H30O3
IUPAC name(1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
InChI IdentifierInChI=1S/C21H30O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h11,15-18,22H,3-10,12H2,1-2H3/t15-,16-,17-,18+,20-,21-/m0/s1
InChI KeyZESRJSPZRDMNHY-YFWFAHHUSA-N
Isomeric SMILES[H][C@@]12CC[C@H](C(=O)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
Average Molecular Weight330.4611
Monoisotopic Molecular Weight330.219494826
Classification
Description Belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent21-hydroxysteroids
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 21-hydroxysteroid
  • Pregnane-skeleton
  • 20-oxosteroid
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • Oxosteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Alpha-hydroxy ketone
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Indirect biological role:

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0002-6971000000-e4a2b497c3f1902376792014-09-20View Spectrum
GC-MSDesoxycorticosterol, 2 MEOX; 1 TMS, GC-MS Spectrumsplash10-0fbl-5910000000-c5e47cf4a734228e8190Spectrum
GC-MSDesoxycorticosterol, non-derivatized, GC-MS Spectrumsplash10-0005-9640000000-847952a8ec3d6fcf23d6Spectrum
GC-MSDesoxycorticosterol, non-derivatized, GC-MS Spectrumsplash10-006t-0491000000-147f3880bd096269f1e5Spectrum
GC-MSDesoxycorticosterol, non-derivatized, GC-MS Spectrumsplash10-0fbl-5910000000-c5e47cf4a734228e8190Spectrum
Predicted GC-MSDesoxycorticosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0g4l-1595000000-d809868c6663b71a3d30Spectrum
Predicted GC-MSDesoxycorticosterol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-1249000000-3bfc1d7ec076060fdbdeSpectrum
Predicted GC-MSDesoxycorticosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDesoxycorticosterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDesoxycorticosterol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDesoxycorticosterol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDesoxycorticosterol, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDesoxycorticosterol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDesoxycorticosterol, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDesoxycorticosterol, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDesoxycorticosterol, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0009000000-e7a6d422ea2bacd462a62012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052b-8900000000-2a8ec06e636135e7f1a62012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052b-9500000000-5f9c88fc7ed062bfa3f92012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0005-9640000000-3a4ef053cdcc6d13ad032012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-006t-0491000000-8f8a662c709ceb10d5a12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00fr-2920000000-4cb1f49316cc482381222017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4j-4921000000-a2171271b5cf1b4be2132017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0532-6966000000-f57233040f10efef4ba92021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-001i-0009000000-0cff8a9a4549636b3f422021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-052b-5910000000-7f1d5740a09ef36424852021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-052b-6900000000-6970a665800f041e96122021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0a4j-9800000000-4a04f32e5cb77516241f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0a6s-9600000000-17d56b65d46a46d9f6532021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0039000000-6c47839c30a0a237e1172017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0il1-2197000000-1c89c50b55ae4c372e762017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-3392000000-381ce772e5eeb46eab9c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0019000000-8ba1d5bf9b1cd5e2ffa32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-072a-2089000000-f762aa07c4d2c9a1ba2d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-3091000000-9170898ad4f59afc21472017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-d95b73baf953ad32ef3d2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ba-0096000000-e24f47a2c3de74d2cbab2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00pj-0091000000-df2a7ff10136d851b3e02021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-aba02f501a0b016a82022021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03yi-0795000000-3e5ec71612f4300e6dac2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-2910000000-f2aa245e24e0a1ca19a42021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDDESOXYCORTICOSTEROL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH 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
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference